Danielle Oteri's Italy

If you loved Ep. 38: How To Plan Multigenerational Travel, this episode is part 2, especially if you’ve accepted the unpopular but very good advice that renting a villa in Tuscany is a bad idea. This episode offers a better alternative.

A quick recap of resources and upcoming events:

* Tuesday, October 6th at 7 pm ET is the next Ask Me Anything About Italy for paid subscribers. This live Q&A with me happens monthly. If you can’t attend live, send me your questions at [email protected]. I’ll answer them live, and you can watch the replay, available the following day.

* Thursday, October 8th at 7 pm ET is a new online class for people with Italian roots. “Finding Your Way Back to Italy” debunks Ellis Island myths and explains why Italians left Italy en masse starting in the 1870s. This history is surprising, but it shouldn’t be—it’s beautiful, but also complex, and you will learn a lot about yourself and your family by understanding the underpinnings of the stories and ways of being you inherited. Click here to register.

Danielle Oteri's Italy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

There are hundreds of books about Italy’s art and food, but you can count on one hand the number of books available about Italy’s nature. The oldest is Pliny’s Natural History, written in the 1st century CE, before he died on a rescue mission to Pompeii. The newest is Edward Cutler’s magnificent “This Beautiful Country,” a joy and a humbling reminder of how much we overlook every day.

I hope you enjoy this episode and let me know what you think in the comments.

Danielle Oteri's Italy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Joseph Walker, author of Buried Italy and the voice behind Italian History with Joseph, spent the early 1990s exploring the submerged Roman resort of Baia and harvesting grapes in the ancient amphitheater at Cuma.

Before Baia had snorkeling schools and glass-bottom boats, Joseph Walker was hiring a local fisherman to take him out into the Gulf of Pozzuoli and swimming down into what turned out to be the nymphaeum of Claudius and Nero. That dive became his life’s work. He arrived in Italy with the U.S. Navy in the late 1980s and never really left. This episode is a long, winding conversation about the Campi Flegrei, the volcanic zone west of Naples where myth and geology keep colliding. Joseph and I share a lot of interests, and this conversation could have gone on for hours.

What we discuss:

* How Walker found Portus Julius and started bringing tourists to see the underwater ruins.

* The Cave of Cumean Synil, how it predates Virgil by roughly 600 years, and Walker’s case for Etruscan involvement in its construction

* The amphitheater at Cuma that isn’t on the archaeological park’s tourist map, and the harvest feast that Walker got invited to as a young man

* Lago d’Averno as one of the mythological entrances to Hades, and the Oscan cult of death that came before the Greeks arrived

* Naples’ own relationship to death and the ritual of adopting bones at the Fontanelle Cemetery

* Bradyseism, the rising and falling of the Campi Flegrei landmass, and the current push to reopen sites like the Piscina Mirabilis to tourism

* How the region’s volcanic history may connect to the extinction of the Neanderthals

We also got into Puglia a bit and discussed:

* Castel del Monte and Frederick II’s use of the octagon as a symbol linking heaven and earth

* The mosaic floor at the Cathedral of Otranto, its King Arthur panel, and the monastery library destroyed in the 1480 Ottoman sack

Find Joseph Walker:italianhistorywithjoseph.com/oteri — includes a free download of seven “Buried Italy” sites and a free chapter of the book (the Narnia chapter, cut from the final edit).

Danielle Oteri's Italy is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Intense, I would say unbearable, summer heat is the new normal in Italy, and it changes how you should be planning a trip. This episode covers when to actually go (spring over fall, with one exception), what to do if summer is your only option, and why “I’m used to heat” doesn’t mean the same thing in Dallas as it does in Rome.

In this episode:

* Why hot summers in Europe can no longer be treated as an anomaly

* Best time to visit for Venice, Florence, Rome: spring (minus Easter week) over the increasingly-booked-out fall

* The seaside strategy for anyone who can only travel in summer — including how to structure a day around the heat

* Why an Italian beach club is a unique cultural experience

* Where to find real sagre and summer festivals

* The single biggest mistake I have to unravel for clients overstuffed itineraries

* Tipping in 2026: what’s expected now for guides, drivers, and restaurant staff — and why even the Germans are tipping.

All podcasts are free, but if you want to hang out with my live, and ask questions, consider becoming a paid subscriber. On August 27th at 8 pm ET, I’ll be doing a Destination Deep Dive on Pompeii, Herculaneum, Baia, and Oplontis. Because even though Pompeii is worthy of a thousand visits, it’s just one piece of the story, and one of these others sites might actually be more appropriate for your trip.

A quick note for paid subscribers: the August Ask Me Anything About Italy will take place on August 13th at 8 pm ET. This month’s Destination Deep Dive will cover Baia, Pompeii, Herculaneum, and Oplontis — the ancient Roman cities around Naples in honor of the new series about Pompeii Out of Time currently streaming on Disney+. We’ll convene here on Substack Live for that on August 27th at 8 pm ET.

Podcast Show Notes: The Fake (Maybe) at the Met

I visited a piece that I absolutely love, but I also think it’s too good to be true. It’s a thymiaterion, an ancient incense burner used for weddings, ceremonies, and funerals, at the Metropolitan Museum of Art: a ring with five figures, each holding a different attribute, like little action figures. I think it could be a pastiche, a mix of something ancient with something modern, if not an outright forgery.

Terracotta group of women seated around a well head

The Instagram post that started it

I posted about it on Instagram, where I wrote: “I love this beautiful thing, but I think it’s a fake. Please prove me wrong.” The post got over 21,000 views and around 110 comments.

The original Instagram post — danielleoteri_italy

Prior owners

Mary Jaharis donated the piece to the Met in 2012. She acquired it at the 1999 Sotheby’s sale of the Christos Bastis collection. Before that, it was on view at the Merrin Gallery in New York until the early eighties.

The Getty’s own former curator of antiquities, Marion True, was put on criminal trial in Italy for conspiring to receive looted antiquities; that trial collapsed in 2010 when the statute of limitations expired. The dealer tied to that network, Giacomo Medici, was convicted in Rome and sentenced to prison. If you’re interested in this topic, I highly recommend “Chasing Aphrodite: The Hunt for Looted Antiquities at the World’s Richest Museum” by Jason Felch and Ralph Frammolino.

Chasing Aphrodite, by Jason Felch and Ralph Frammolino

Also, my apologies to Ralph Frammolino — I mispronounced your name in the recording.

The tombaroli and Taranto

The word for the people who do the tomb robbing is tombaroli. Taranto, in Puglia, is one of the most abused archaeological sites there is; its old city, la città vecchia, is Greek, filled with underground burial chambers that smugglers have used for storage in more recent times.

Museum of Looted Art

I got a message from an Instagram account called Museum of Looted Art, pointing me to their database of documented looted works, specifically the history of the Merrin Gallery. MoLA is a project of Jason Felch, author of Chasing Aphrodite.

The Tanagra connection

The figures are most closely aligned with those of Tanagra. In the 1860s, hundreds of these terracotta figures were accidentally discovered by farmers plowing their fields. When they first appeared on the French art market around 1871, collectors and artists went wild, calling them the Parisians of Antiquity. They were displayed at the Paris World’s Fair in 1878.

More about Tanagra figures here.

A more recent parallel: the flood of fakes in Islamic art tied to wealthy collectors in Doha, Dubai, and Abu Dhabi since the early 2000s, and the “Salvator Mundi” painting sold at Christie’s in 2017 for $450 million, which I have never for one minute believed was an authentic Leonardo.

Coverage of the Salvator Mundi sale

Paestum

Throughout the Southern Italian Greek colonies, most notably Paestum, you find hundreds, potentially thousands, of terracotta heads with an incense burner, often in the form of a flower, from the sanctuary of Hera. Many are on display in the museum right next to the archaeological park, but none show five women in a composition like this one.

Why testing doesn’t settle it

The main dating tool is thermoluminescence, which measures the energy stored in an object since it was last fired. Forgers can defeat this: carving fakes from genuinely ancient fired material, grinding real ancient ceramic into new clay, or artificially irradiating pieces with X-ray equipment.

Where I landed

I don’t love it quite as much as I did. I still very much want it to be real, but I’m going to trust my initial reaction here and say I don’t believe it. I’m not accusing the Met of anything nefarious; I don’t know the politics behind this object’s display, and I’ll leave open the possibility that the curators have good reason to believe it’s real.

What I hope this episode has done is made you more curious. Let me know what you think in the comments.

I recorded this voice note from Borgo La Pietraia, where I’m currently recovering and preparing for a busy travel schedule in the days ahead. Now, as I prepare to hit send, I’m sitting with Arianna, my business partner, technically a 4th cousin, and, in every other way, my sister. We have decided to offer a small group experience in late October. The reason? The property’s olive trees come in every other year; this year, we’ll have a harvest and make olive oil. We focused and put together all the details this morning, with an itinerary based on the popular Episode 35: The Mozzarella Highway. (The text of that episode is below.)

If you’d like to join us, all the information is here: https://www.feasttravel.com/cilento

Also, a quick note for paid subscribers: the next Ask Me Anything About Italy will be July 23rd at 8 pm ET.

The most delicious thing you can eat in Southern Italy is buffalo milk mozzarella. Italy has earned such a sterling culinary reputation that most people just open their mouths and say yes to whatever is put in front of them. But every once in a while, someone says buffalo mozzarella, what the hell is that?

It is a strange thing to encounter, especially because the languid, enormous, but very sensitive water buffalo are cugini to the ones you’ll find in Vietnam or Cambodia, where buffalo milk mozzarella is not a thing. Buffalo mozzarella is made primarily in the region of Campania. It graces pizzas in Naples and has a different casein than most cow’s milk, so the lactose-intolerant among us can indulge. Buffalo farms abound in Caserta, near the stupendous Palace of Caserta, from where the Bourbon monarchy ruled over “the Kingdom of the Two Sicilies.” Before Italy became the nation we know it as today in 1861, it was a monarchy that pioneered several industries, including a dairy industry based on buffalo milk. But even more exquisite is the stuff made at a handful of farms, a little farther south.

If you’re driving there, maybe on a day trip from Naples or the Amalfi Coast, you’ll inevitably get snarled in traffic on what locals call “the mozzarella highway” through Battipaglia. Every sign on the roadside is flashing mozzarella di bufala. The traffic is largely due to hundreds of trucks that pass through daily to pick up mozzarella and transport it to supermarkets across Italy. I’ve heard waiters in Florence extol the virtues of its freshness, boasting that it just arrived in the restaurant that afternoon. I’ve also heard waiters in New York cooing that they just picked it up from JFK that morning. Keep driving; Battipaglia is an industrial farming zone, and everything is pasteurized for export. Better things await in the town called Capaccio-Paestum.

Paestum is most famous for three extraordinarily well-preserved Greek temples. They are massive and built of travertine, a volcanic stone, then coated in plaster and painted to mimic marble, which doesn’t exist in Southern Italy. Paestum was colonized by Greeks, conquered by Lucanians, who were the indigenous people of the area, whom the Greeks employed as their security goons, and then became a Roman city. Paestum was considered very old when the Romans conquered it. The oldest of the three temples was 280 years old. The Greeks regarded everything around the temples as sacred ground, but the Romans were insatiable real estate developers. There developed markets, civic buildings, a large Asclepieion, which was the closest thing to a hospital in the classical world, and dozens of smaller temples, all surrounding the big, very old ones.

Roman Paestum was bigger and far more important than Pompeii or Herculaneum, and though it’s beyond the reach of Mount Vesuvius’s molten tentacles, it is still affected by earthquakes. The Roman Empire declined, and Paestum sank. Literally. The reason: a phenomenon called bradyseism, which is a Greek word: bradys means slow, and seismos means movement.” It’s an imperceptible but continuous slow rising and falling of the earth - a slow-motion earthquake.

When the Greeks built the temples close to the glittering Tyrrhenian sea, things were on the up. But by the third and fourth centuries, Paestum was a swamp, infested with malaria carrying mosquitos. Mal aria means ‘bad air.”

The Paestani fled for the hills. Some went to the hills just above Paestum, founding Capaccio, my grandmother’s hometown, while others went higher to the sea-facing cliffs of the Amalfi Coast. The name Positano may be related to the Paestani who settled there.

And certainly people also went to Salerno, which was a Roman city, then under Lombard rule, and in 1077 was officially conquered by the Normans, proud descendants of the Vikings, loosely related to the Normans who just 11 years earlier had taken England at the Battle of Hastings. Salerno was a luxurious city, full of international merchants, and home to the world’s first medical school. Meanwhile, once glorious Paestum, not very far away at all, must have looked like the zombie apocalypse.

Just to let you know, I haven’t forgotten we were talking about buffalo and delicious cheese; they will soon re-enter our story, but first we need to stop in Salerno.

Salerno was where the Norman king built a cathedral dedicated to Saint Matthew the Apostle. It’s believed he died in either Ethiopia or Persia, but his bones somehow ended up near Paestum, and two people had a dream, alerting them to the location. They retrieved the old bones, and the cathedral was built around them. The Normans also began to adorn the area we now call the centro storico of Salerno with Roman columns from Paestum. They’re embedded in many corners, and sometimes you’ll see a sign with a dog lifting its leg and a red line across it. It may read “Questa e storia” - this is history, and don’t let your dog pee on it. The massive columns that you’ll encounter in the courtyard of the cathedral came from what must have been another enormous temple at Paestum, which was clearly functioning as an open quarry.

Why? Because using Roman columns made an architectural argument that the new power is heir to the Roman one. For someone from somewhere else, Northern France in this case, to frame himself as the legitimate successor to Roman Caesars. And how did they physically pull them out of the swamp and drag them back to Salerno? With water buffalo, which are naturally immune to malaria.

Buffalo arrived on Italian soil via Arab merchants, who first brought them from Southeast Asia to Egypt for use as work animals. For roughly two centuries, Sicily was under Muslim rule, first governed by emirs from North Africa. Sicily was wealthy and well-developed, so much so that the various wealthy factions descended into infighting, which allowed the Normans to conquer them more easily. Neither gentlemen nor scholars, they kept what the Arabs did best, including mathematics, agricultural practices, and sugary desserts such as cannoli. Buffalo thrived in the marshy lands along the Italian coast and were incredibly effective at doing the impossible work of clearing rivers. As they plod through streams, the underwater reeds that are nearly impossible for humans to remove will tangle around the legs of a buffalo sauntering through the day and easily snap and break.

Paestum doesn’t appear in the historical record again until the 1700s, during the period known as the Grand Tour. Part of a complete education was a trip to the Italian peninsula, where something astonishing had happened. Pompeii was discovered. The Bourbon kings of Naples not only founded the buffalo mozzarella industry, but also the field of archaeology, which didn’t exist. Pompeii fever swept the educated world and set off the Neoclassical movement. Paestum, though never completely abandoned, defined the word backwater, and was a more adventurous leg of the Grand Tour. In paintings from this period, you can see these beautiful Doric temples, their reflections in pools of water, and grazing buffalo all around them.

Can you imagine what a sight that must have been to citified elites from England and Germany? People who had never seen or even imagined a buffalo, or were accustomed to having their dopamine spiked by imagery hundreds of times every day?

In those paintings, you’ll also notice houses, and the locals – my ancestors – guiding the buffalo, or sitting on a hill wearing loose pants and a floppy hat, playing a flute, or some other peasanty activity. As a sidenote, I don’t understand how my lineage in this area survived long enough to produce me, as I am target number one on every mosquito’s agenda.

When you arrive in Paestum today, you will also find the very best farms producing buffalo-milk mozzarella within a mile of the temples. Most well-reputed is Tenuta Vannulo, a local family-owned farm that has made artisanal cheesemaking and the highest standards of animal welfare a point of attraction. You can tour the facility and watch buffalo using state-of-the-art self-milking machines, getting massages with what look like car-wash brushes, while a guide explains how Mozart is played for them in their pens. The result is a product unlike anything on the mozzarella highway, and it is exquisite. I especially recommend the buffalo milk gelato. If you’re a coffee person, get the coffee flavor, drowned with a shot of espresso. (To the uninitiated, this is called an affogato.) That’s it, that’s the peak coffee experience of your life.

But my favorite place is Barlotti, partially because it’s within walking distance of the Paestum temples. You don’t have the full organized tour experience that you have at Vannulo, but you can hang out with the buffalo, who are very quiet and relaxed in a very Southern Italian way. Have lunch inside their beautiful glass-encased restaurant or in the garden underneath the pergola. Don’t overthink your menu choices. Get the sample plate that includes fresh mozzarella, smoked mozzarella, and a mound of ricotta, followed by a plate of cooked vegetables, a selection of whatever is growing at the moment. For dessert, a cannoli filled with buffalo milk ricotta.

After lunch, walk to the Paestum temples. The swamp was officially drained in the 1930s by the Fascists, another group that sought to legitimize itself by resuscitating Roman ruins, and the ground continues to be managed today. After the war, when malaria was eradicated, a modern Paestum was fully developed. If you walk on the right side of the road, you’ll see water running – there are ancient springs here, which certainly inspired the placement of the temples nearly 3,000 years ago. The presence of the Asclepieion, natural springs, and temples together indicates that the Greek colonists identified this as a place of healing. And you can squint past the sunlight and use your imagination to see a parade of buffalo, pulling a plow with a giant Roman column atop it, en route to Salerno. Because everything good from the old world should be used to build the new one.

This month Christopher Nolan’s Odyssey hits IMAX, giving me the perfect excuse to talk about where the epic actually happened. Consider it the earliest travelogue of southern Italy, tracking a the journey from Circe’s mountain outside Rome down through the Scylla’s wrath in Calabria. Travel writer Laura Itzkowitz of The New Roman Times joins to talk about the Riviera di Ulisse, the beach clubs that haven’t changed since the 1950, and the mythic beauty of Calabria and Capri.

In this episode:

* The Bronze Age Collapse, and how the Odyssey emerged from that dark age

* The Nestor Cup on Ischia and the earliest written Greek in the region

* The Riviera di Ulisse: Monte Circeo, Sabaudia, San Felice Circeo, Sperlonga, Terracina, Gaeta

* Where Lazio starts feeling like Campania (and why)

* Laura’s mystery cruise from Athens through Magna Graecia

* Scilla, the Riace Bronzes, and the archaeological museum in Reggio Calabria

* The many legends of the sirens and what they really mean

* Capri: how best to enjoy it

* The Aeolian Islands and the god of the winds

If you want to learn more about the Bronze Age Collapse, I highly recommend Eric Cline’s 1177 BC: The Year Civilization Collapsed.

The Ulysses Coast

Thanks to Laura for these recommendations:

* Saporetti — the old school beach club in Sabaudia

* Hotel La Nave — retro family-run hotel in Sperlonga

* Bazzano Beach — beach club in Sperlonga

Laura also wrote about beaches on the Riviera d’Ulisse for a Lazio special edition of Bellissimo, Italy Magazine’s quarterly e-magazine for paid subscribers, and included several of these towns in her list of best beach towns near Rome on The New Roman Times.

You can read Laura’s Afar piece on Windstar’s mystery cruise here.

And in keeping with my advice to never trust an Italian website — the website for Sperlonga’s archaeological park, Villa di Tiberio is —- not working. But don’t be disssuaded, definitely go there, it’s amazing!

Ischia & Capri

The Nestor Cup is at Villa Arbusto on Ischia. Here’s my Ischia Deep Dive for more.

On Capri, this is Farella, the textile studio Laura describes.

We didn’t discuss it, but the Li Galli islands are strongly tied to the sirens as well — which is why the most famous hotel on the Amalfi Coast, Positano’s Le Sirenuse, takes its name.

Cilento

The siren Leucosia is said to have washed ashore near Castelabate on the Cilento coast — one of three regional claims on the myth, alongside Capri and Sicily. My Cilento Deep Dive has the fuller history if this coast is new to you.

Join us, free or paid, the conversation here is always full of interesting stories you won’t find elsewhere

Packing reliably stresses people out, and almost always, people pack more than they need. Less is more, plus you can buy anything you need in Italy, so don’t worry.

Ideally, you need just a four-wheeled suitcase and a carry-on bag. I have a Calpak backpack with a strap on the back that slides right onto the suitcase handle. It also fits my 16-inch laptop. Any system that is too complicated stresses me out, so I keep my stuff organized while traveling with packing cubes. They let you move from place to place without fully unpacking, and they make it easy to see exactly what you have to work with in your capsule wardrobe. They also prevent me from overpacking by forcing me to look at all my clothes as a system and make sure everything goes together.

Ensure your day bag has ample space for your passport, a phone charger, and sunglasses. You may want to bring a couple of cotton tote bags if you’d like to carry a sketchbook or do any grocery shopping during your trip.

For the women who want a detailed list with links, here we go:

* Two to four pairs of cotton or linen pants in neutral colors

* Jeans, but not skinny jeans, in the summer. If you’re traveling in a cool season, and you’re a jeans person, bring 2 or 3 pairs

* One casual dress

* 5-8 T-shirts and tank tops (if traveling in winter, substitute T-shirts for simple sweaters). You can get a variety of scoop necks and V-necks. Get them at Uniqlo, J.Crew Factory, AYR, or Perfect White Tee

* 1 blouse in a print or bright color. This is your going-out shirt. (Remember the aughts, my elder Millennial friends.)

* 1 blazer or cardigan

* 1 cotton scarf

* 1 pair of pajamas, cotton

* Bras, panties, of course

* 1 pair of simple white trainers

* 1 pair of ballet flats or loafers

* Sunglasses

* 1 white or blue collared shirt

Let’s get more specific:

This dress from Marine Layer. You can roll it up, stuff it into a beach bag, drive a FIAT over it, and it still looks great.

I wear jeans almost every day, and that makes traveling easy. They match with everything, don’t show panty lines, don’t wrinkle, and don’t need to be washed as much. However, if you’re traveling in the hottest months, they’re not ideal, though I find these wide-leg jeans from Kut From the Kloth to be cool and comfortable. Just make sure to size down with this brand. I’m a size 8, but I got these in 6 petite, and they're still a little roomy.

This Frank & Eileen blazer seems wildly expensive for an unlined jacket, but I have done unspeakable things to it over the course of 5 years, and it has retained its shape and looks fantastic with everything. You don’t have to buy this one specifically, but the idea is to bring a casual, versatile jacket that adds a little polish to your lewk while still being low-maintenance.

These shirts from AYR are worth every penny. Button them up, wear them open over a tank top, or use them as beach cover-ups. You can pretty much wear this shirt with a mix of tanks and dresses for your entire trip.

I also love these scoop neck shirts from AYR. The black-and-white striped one has been out of stock forever, but it’s the most useful shirt I own. It’s soft and light and pairs with everything.

* Bombas socks. They are just so well-made and give you a little extra cushion for those 20,000-step days.

* A toiletries bag with a hook to hang on the back of the bathroom door.

* Miracle Balm from Jones Road is indeed a miracle. I travel with the Flushed shade, a tube of their black mascara, and lipstick. I think Korres makes the best lip balm ever.

* A Tide pen that’s always in my purse.

* Soak for hand-washing undies in the sink.

I’m not getting a kick-back on any of these items, but Bobbi Brown, if you wanna send me some mascara, I’m almost out. Danielle Oteri's Italy is a reader-supported publication. If you enjoy my work and want to support it, consider becoming a free or paid subscriber.

The Italian Pharmacy

Hyaluronic acid, particularly the French brands. I see a major difference, and I’ve got one of those Anna Magnani faces that has a distinct line and wrinkle that appears instantly for everything I don’t like or find even mildly suspicious.

Note: This is not medical advice, and I’m not a doctor. This is something I personally buy and use. OKI is a popular Italian over-the-counter and prescription painkiller. It contains Ketoprofen lysine salt, an NSAID used across Italy to treat headaches, toothaches, menstrual cramps, joint pain, and sore throats. I’m not a doctor; I’m not giving you medical information. Obviously, check with your doctor, but as a lifelong migraine sufferer, this is like a religious experience. Again, I’m not a doctor, and definitely not your doctor. I’m just sharing my experience, not giving you medical advice.

Pack your toiletries in a bag that can unfold and hang by a hook on the back of the bathroom drawer. Especially in cities, hotel bathrooms can be tiny, and you won’t have to store your things in the bidet if you bring the right stuff.

For the men

Man friends, if you’re actually reading this, my advice is to keep your clothes simple like Stanley Tucci. Cotton pants or jeans, a polo shirt with a collar you can pop if you’re feeling the Italian vibes.

If you want to really look like an Italian man, wear lots of blue, and also blue on blue. Again, no one nails it quite like Stanley.

And finally, the Italian word for a blow-out is piega. Want to get your roots done? The term is la ricrescita.

There’s a hotel in Naples that’s perfect for the night before a flight. In fact, all the United pilots and flight attendants stay there. The hotel is pretty standard and part of a chain, but the building itself is the only “skyscraper” in Naples, which is 24 floors high. As a New Yorker, this is funny to me, but the elevator is a little anxiety-inducing, since Naples is, of course, very prone to earthquakes. But all the rooms have beautiful views, depending on which side of the hotel you’re on: either over the bay of Naples toward elegant Posillipo, or toward the historic center, which I prefer, because it’s a fascinating top-down view of one of the oldest urban grids on earth.

You can see Spaccanapoli, the street that cuts a straight line across the old part of town — spaccare means to split, and the splitter is the original decumanus, the main east-west road of the original Greek city. The city is tightly woven, almost impossibly dense, and what catches my eye are the cloisters: enclosed gardens adjacent to churches, tucked right into the urban fabric. The largest cloister I can see from my hotel window is Santa Chiara, attached to one of Naples’ most historic and beloved churches. It’s a Gothic church built when the city was ruled by the French Angevins, and it has both a monastery and a convent, residences for Franciscan monks and nuns called the Poor Clares, separate, of course. There are still monks and nuns in residence, but in a separate, smaller area, separate from the nuns’ cloister garden, which is a major tourist attraction today for its beautiful majolica tile.

A cloister is an enclosed garden, which comes from the Latin word claustrum, which you will understand immediately if you suffer from claustrophobia, a fear of enclosed spaces. It’s open to the sky, but enclosed on four sides, with gardens designed for some practicalities but also for spiritual contemplation. Frequently, you will find four paths, which form a giant cross, but are also meant to evoke the four rivers of paradise. Also worth noting, the word paradise is a Persian word which means enclosed garden. It was a place of spiritual meditation and prayer. And as an outdoor space, it had practical functions — you can imagine people doing laundry there, getting some exercise, breathing fresh air.

I recognize the cloister not just as a historian, but viscerally, because I spent 16 years working at a museum called The Cloisters, in New York City. The Cloisters is the medieval branch of the Metropolitan Museum of Art, built from pieces of actual French cloisters, and a full apse from Spain that was deconstructed, shipped across the Atlantic, and reconstructed in upper Manhattan. It’s an entirely secular space, but it feels like a spiritual one. I know what it feels like to spend your days inside one of these places, inside an otherwise busy city. It is beautiful and serene, but also isolating and lonely. But I will say this, even on the loneliest days in late January when maybe only 50 visitors would come to the museum, and the staff was bored and mildly depressed and snipping at each other, and the sky was gray, and the gardens were dead, the space always felt privileged.

Who took monastic vows and why

For centuries, specifically in the centuries we label as the Middle Ages and the Renaissance, the cloisters of monasteries and convents were full of monks and nuns; today, this is no longer the case. And that’s not necessarily due to a spiritual crisis because most people did not end up in a monastery by calling. Your family put you there, and they had very specific reasons for doing so.

For sons: the eldest inherited the family fortune. Younger sons could work in the family business if there was one, or go into the military or the church. But deliberately placing a son in a monastery could be an act of piety, though it was often political. If he rose to become an abbot or a bishop, he controlled land and credit networks and could leverage political influence that could directly benefit the family.

For daughters, the issue was a dowry. In wealthy Venice, the cost of a dowry for a merchant family quadrupled in the early 16th century. In Rome, dowries climbed steadily over the course of the 1500s, inflation driven by status competition between elite families. In contrast, you could place a daughter in a convent for roughly 20 times less, so for a family with multiple daughters, that was an easy decision. In 16th-century Florence, more than a quarter of women from elite families entered religious institutions. In Venice, some estimates go as high as 60%.

There were metaphysical motivations as well, primarily the issue of purgatory — this temporary state of purification and suffering for souls that aren’t hellbound, but also don’t have the GPA to go straight to heaven. The prayers of the living, especially monastics, people devoted full time to God, without any distractions or opportunities to sin, which would dilute their spiritual intensity, could shorten that time for family in heaven’s waiting room. The more Masses said for the soul existing in purgatory, the more prayers, the more beautiful art and music that the family patronized for the glorification of God, the better. And the family members who lived in the monasteries and convents were like a stock, compounding spiritual interest over a lifetime.

But families didn’t just park their children in a cell and forget about them. They financially supported the community in which they lived and sometimes even funded private apartments. Those from lesser means did physical labor, while the wealthier ones held power. The convent was one of the few places where women could hold power in an official capacity. On the walls of Goleto Abbey, a gorgeous ruin in the countryside near Avellino, there is a fresco of a nun named Scolastica who holds a bishop’s staff, signifying she held that level of status. Goleto Abbey, by the way, is beautiful even if it was almost completely destroyed. It no longer has a roof, but it’s like walking around inside a Gothic skeleton, in the middle of a lush meadow, surrounded by rolling mountains where vineyards produce Aglianico, Falanghina, and Greco di Tufo.

But I am digressing from my point that monasteries and convents are where you find the most beautiful art, architecture, and music, and are an enormous part of Italian culture; in one way or another, you will encounter them on your trip to Italy. Moreover, much of the art in famous museums like the Uffizi was originally made for churches and later displaced. I think that if you’re not already an art lover, viewing art in museums is challenging because you’re totally lacking the context for which the artwork was intended. To understand why those artworks got displaced — and also why so many 5-star hotels in Italy were once convents or monasteries — you have to understand one of the most dramatic cultural ruptures in Italian history.

A Hinge Point in Italian History

When Napoleon Bonaparte crossed the Alps into northern Italy in 1796, he did so with the idea that the Church was an instrument of oppression, that its hoarded wealth belonged to the people, and that the monastic life was a waste of time. In Bologna, Venice, Milan, and Rome, he ordered the suppression of religious orders, and monks and nuns were expelled from their houses so the properties could be seized by the state. It’s also important to remember this was about 65 years before the nation of Italy that we know today was formed, so he was invading a series of kingdoms and papal states, where the church held enormous power.

In Bologna alone, which had a population of about 70,000, there were 70 convents and monasteries. Napoleon’s law gave them six months’ notice: any monastery with fewer than fifteen local members was dissolved immediately. The rest were consolidated, taxed, and stripped. And the artwork was being evicted and stolen simultaneously. Tommaso Puccini, an official of the Uffizi and the Pitti Palace, secretly loaded 75 crates of Florence’s most precious artworks and dispatched them to Sicily on a British frigate, just to keep them out of Napoleon’s hands.

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He didn’t save everything. Napoleon’s commissars moved systematically through Italy’s churches, convents, and palaces, pulling paintings off walls and loading them onto wagons headed for Paris. A significant part of the Louvre was built on this confiscation. If you’ve visited the Louvre and been surprised by the endless galleries of Italian Renaissance masterpieces, they are there in large part because Napoleon took them. The masterpieces that didn’t go to Paris were concentrated into newly created civic museums in Italian cities.

The most significant was the Pinacoteca di Brera in Milan, called by Napoleon the “Italian Louvre,” and it was filled almost entirely with paintings stripped from churches and convents across northern Italy and Venice in particular. The word pinacoteca means painting gallery.

The Brera doesn’t have the splendor of the Louvre, and it’s not on the tourist radar in the same way as the Uffizi, but if you’re visiting Milan, it’s an incredible museum and a better investment of your time than visiting Leonardo’s Last Supper. Also, the reason it’s so hard to get tickets to see the Last Supper is that it’s in its original place — a convent, where the scene was painted on the wall of the dining room where the nuns ate. Leonardo used oil paint on a dry plaster wall rather than the traditional fresco technique, and the wall opposite the dining room was the kitchen. When the kitchen heated up, the paint began to deteriorate, and the Last Supper has been pretty much a disaster ever since. It’s been repainted many times, and if Leonardo hadn’t been so famous both in his day and after, that painting would have long been gone. Back to the Pinacoteca Brera — it shares a space with the art school, so there are always many art students sketching in the courtyard. And once inside, especially if you took art history in college, it’s just one greatest hit after the other. Because everything here was stripped out of the most beautiful, well-funded churches, convents, and monasteries from across northern Italy. When you consider the extraordinary wealth of the Republic of Venice in particular, and then think about the amount of patronage that produced, you can start to appreciate why any art lover needs to visit the Brera.

After Napoleon fell, the modern nation of Italy was formed in the 1860s, and the new secular Italian state dissolved all remaining religious orders and confiscated their properties. The buildings were converted into schools, courthouses, hospitals, barracks, and prisons, or were simply left vacant.

By the late 19th century, thousands of magnificent medieval and Renaissance buildings — built to last, set in extraordinary landscapes, with thick walls, vaulted ceilings, and large communal spaces — were rotting. At the same time, Italy was experiencing mass emigration, mostly from the South, but not exclusively. People left Liguria and Tuscany for California and Argentina, laying the foundations of the future wine industry in those places. Then, as Italy’s tourism economy grew in the 20th century, these buildings began to be used as hotels. The cells were already the right size for guest rooms. The refectory — where the monks had eaten in silence — was already a dining room. The wine cellar was already a wine cellar, and the cloisters were a perfect courtyard.

Indulge me this one short rant….

Before I share with you a few of the hotels you should know about, indulge me with this little rant. I know a tour operator who has a very quiet “no church” policy on their tours. This person, like Napoleon, I guess, is strongly anti-clerical and believes her clients think churches are boring anyway. And I want to be clear when I say, whatever your personal beliefs are, and those belong to you, and I respect them completely. But if you choose not to visit any churches during your trip to Italy, you may as well not visit Italy at all. Catholicism is a fundamental piece of Italian culture, even today, when most Italians aren’t particularly religious.

And I would apply this idea to visiting any country where faith and religion have shaped the culture. I have covered my head to visit a mosque and removed my shoes to visit a Hindu temple because any space that people have entered for centuries to be in relationship with the metaphysical world is one of the most interesting, meaningful, and potentially transformative opportunities that come with travel. To reject it would be like going to Italy and eating peanut butter and jelly sandwiches in your hotel room because you’re not willing to try Italian food.

Monasteries Turned Five-Star Hotels

Across Italy, in any region, you will find beautiful hotels named Monastero or Convento — because that’s what they were. I have wondered to myself if occupying these spaces is a desecration, but really, no, the wealth and the status were always here too.

The most famous example is probably San Domenico in Taormina, a very swish Four Seasons hotel now famous for having been the set of season 2 of The White Lotus.

Castel Monastero in Tuscany is a social media darling, a 5-star resort created from an 11th-century monastery. It delivers on every Tuscan dream there is, from cypress-lined roads to hot air balloons. The wine cellar has always been epic, both when it was a monastery and now. The property has been enhanced with pools and a spa, and a Michelin-starred restaurant that was run by Gordon Ramsay for several years. And all the marketing copy promises to deliver the tranquility and peace of the original monastic atmosphere.

My dream hotel is the Monastero Santa Rosa on the Amalfi Coast. Fifteen hundred dollars a night is the starting place. It’s on the Amalfi Coast but not near the water. The monks and nuns were not going swimming — and more practically, malaria was an enormous problem at lower elevations. They built high, above where the mosquitoes could reach them. Which means they have the most incredible views, and now there is an extraordinary, Instagram-famous infinity pool. The restaurant is called Il Refettorio — the refectory, where the nuns once ate together in communal silence. It is now a Michelin-starred restaurant.

And then there’s the sfogliatella. The shell-shaped pastry filled with ricotta cream — the signature pastry of Naples — has its origin legend at this monastery. If you go to Amalfi, find Andrea Pansa right next to the cathedral, and order the Santa Rosa sfogliatella. It has an amarena cherry in the center.

Life At the Bottom of an Ancient Lake

If you really want to step into this experience and go far off the beaten path, head to Padula. You’ll need to drive through the Cilento National Park — one of the largest protected areas in Italy — past hilltop villages that see almost no foreign tourists. The drive is easy because the population around here is tiny, and there are few people on the highway. Along the way, you’ll notice little hilltop villages that were there 700 years ago when the monastery at Padula was built. And then, on the valley floor, below the village of Padula, you come to the Certosa.

The Certosa di San Lorenzo is the largest monastery in Italy and has the largest cloister in the world. Over 51,500 square meters. 320 rooms and halls. A great cloister measuring 12,000 square meters, ringed by 84 columns. It is magnificent. Also, unless there’s a school bus parked out front, you may very likely be in this enormous space all by yourself.

In 1306, this was not the middle of nowhere, but a critical corridor. It was the main overland route connecting Naples to Puglia to Calabria — an important road that the Romans called the Via Popilia, which had run straight through this valley since the 2nd century BC. If you controlled this area, you also controlled all the movement through southern Italy.

When Tommaso Sanseverino founded the Certosa di Padula in 1306, he deliberately chose the Carthusians. They originated in France, and at that time, the French Angevins ruled from Naples. But more importantly, Carthusian monks would be able to work the land, which at that time was a flooded marsh. The Carthusians’ engineering expertise came directly from their Rule: because each monk lived in complete solitude in his own cell, the order required individual running water to be piped to every cell in every monastery they built, which made hydraulic engineering an institutional skill they carried with them wherever they went. At Padula, that same expertise drained the valley floor — the silted bed of an ancient lake — turning it into some of the most productive agricultural land in the region. The result was that the Certosa became not just a spiritual institution but an economic powerhouse, controlling the farmland, the water, and the road traffic of the entire valley for five centuries.

When Charles V passed through in 1535 on his way back from defeating the Ottoman fleet at Tunis, he stopped here — not because Padula was remote, but because the Certosa was the grandest and best-provisioned stopping point on the entire road through southern Italy. The monks fed his entire army. For the Emperor’s breakfast, they made a frittata with 1,000 eggs. He stayed two days and confirmed the monastery’s privileges in gratitude. Today, every August 10th, the town of Padula still cooks an enormous frittata in the piazza to commemorate the visit.

When Napoleon’s forces suppressed the Certosa in 1807, they stripped five centuries of accumulated wealth: 172 paintings alone were carted to the Royal Museum of Naples — what is now Capodimonte — while manuscripts and documents were absorbed into Neapolitan state archives, and we can assume quite a lot was sold, stolen, damaged, or destroyed. After Napoleon’s fall, the monks briefly returned, but the Italian unification ended monastic life there permanently. The gorgeous structure became a military barracks, then an orphanage for boys, and then a WWI prisoner-of-war camp. What survives at Padula today — the architecture, the elliptical staircase, the ceramic floors — is essentially what was too heavy or too fixed to steal.

But what remains is an extraordinary peace. The fresh air, the pristine landscape. The ability to imagine what a life here was like, quiet, contemplative — the hum of all those monks, all moving in patterns of silence. Then you go up to the village of Padula and look down at the Certosa and across the landscape, and understand that you’re looking at the bottom of an ancient lake that was masterfully engineered by monks 800 years ago.

The monastery is a museum now, formalized in the 1980s, and UNESCO-listed in 1998. There’s a museum of Lucanian art there that’s not often open, and some contemporary art installed, which… is not good. My favorite part to visit is the kitchen, with a great stone fireplace and a copper sink, and beautiful ceramic tile from Vietri sul Mare on the Amalfi Coast. A monumental elliptical marble staircase — a double helix in white stone — leads to the library. It was the last addition to the monastery before Napoleonic suppression.

You can also have lunch in Padula. Just make sure you eat before 2 pm because the whole town shuts down for the afternoon and doesn’t re-open until dinnertime.

Where the Monks Still Pray

Let’s go back to Naples, where we started this episode. Naples has over 600 churches, and many of them are built atop Roman and Greek temples. But I want to walk just a short distance away to San Domenico Maggiore, a church we first visited in Episode 4: Vittoria Colonna Had It All. It was once the most important church in Naples, and I strongly believe it should be better known today. If you remember that episode, the Aragonese kings of Naples are buried there, and after the 1980 earthquake rocked their tombs, their skeletons were studied by paleo-archaeologists, revealing something very surprising that you’ll just have to listen to that episode to learn.

At San Domenico, in the 13th century, a young nobleman named Tommaso first encountered the Dominican friars. Tommaso was the youngest son in his family, whose brothers had gone into military service, while he was to follow in his uncle’s footsteps and become the abbot of Monte Cassino, the great Benedictine monastery near their home in Aquino. But after receiving his early education at the monastery, his family sent him to the university in Naples, where he would discover the Dominicans — a mendicant order of poverty, wanderers, preachers in beggars’ robes — and he decided that was the life he wanted, not the cushy life of a Monte Cassino monk. His mother was so furious, she had him kidnapped and held at the family castle for over a year to talk him out of it. It didn’t work, and he began a long career between Naples, Paris, Rome, and Orvieto, writing many of the most important texts in the Catholic intellectual tradition.

From 1272 to 1274, the man we call St. Thomas Aquinas was given the opportunity to set up a school anywhere he wished, and he chose Naples. He lived in the monastery at San Domenico and wrote the third part of the Summa Theologica — a systematic, comprehensive attempt to reconcile faith and reason and insist that rigorous intellectual inquiry and deep faith are not enemies. And this is why Thomas Aquinas is having a remarkable moment right now.

There is currently a significant wave of conversion to Catholicism underway, and much of it is coming from Silicon Valley. The engineers, philosophers, and venture capitalists grappling with the implications of artificial intelligence are finding that the medieval Church thought deeply about consciousness, personhood, and the nature of intelligence. The Vatican has been hosting conversations with AI leaders, and Thomas Aquinas keeps appearing in those conversations, because he asked the right questions.

You can visit the church of San Domenico for free, but if you pay the extra 10 euros, you can visit the monastery and visit St. Thomas’s cell. There, witnesses reported that they found him before dawn, suspended three feet off the ground in prayer before a crucifix, completely oblivious to the world. A voice reportedly came from the crucifix and asked what reward he wanted; he said, “nothing but you, Lord.” There’s also a reliquary holding a piece of bone that belonged to St. Thomas’s arm, and pilgrims will go there to pray in front of it. There’s also a heart of someone — we don’t know who — but at one point there were the hearts of three different Neapolitan kings, all lost when, you guessed it, Napoleon’s troops suppressed the monastery.

But San Domenico is somehow still active. There are just a few brothers still there, all elderly. If you pass through the monastery to see St. Thomas’s cell, and it’s just before lunchtime, you might smell the pasta al forno — what we call baked ziti.

I pray the monk’s cells at San Domenico never become a hotel. I hope there’s a renaissance of visitors who want to see this beautiful place. Please put it on your itinerary. Go to learn more about it, but also to feel it. I remember my friend Don saying that he didn’t like to go to yoga classes at the gym, that he liked this yoga center on 14th street in New York City, because it had been a yoga studio for decades, and he said places that have been meditated and prayed in for a long time have a sort of patina, a peaceful vibe that facilitates the experience. The monastery cells at San Domenico have been active for 800 years.

That’s why I want you to go to San Domenico.

🗺️ SHOW NOTES & RESOURCES

Everything you need to plan your own visit.

🏨 WHERE TO STAY

NH Napoli Panorama (the hotel at the top of the episode)Naples’s tallest building — 24 floors — with rooms facing either the Bay of Naples toward Posillipo, or over the historic center toward Spaccanapoli. A practical base for a night before a flight or a first night in the city.📍 Via Medina 70, Naples🌐 nh-hotels.com/en/hotel/nh-napoli-panorama

Monastero Santa Rosa Hotel & Spa (my dream hotel)A 17th-century convent perched on the cliffside above Conca dei Marini on the Amalfi Coast. 20 rooms, an infinity pool carved into the cliff, and the Michelin-starred restaurant Il Refettorio — the nuns’ former dining hall. The spa is the original convent winery. Open April through early November. Starting around $1,500/night. No guests under 16.📍 Via Roma 2, Conca dei Marini (Amalfi Coast)📞 +39 089 832 1199🌐 monasterosantarosa.com

Castel Monastero (Tuscany)A 5-star resort built within an 11th-century monastery and medieval hamlet in the Chianti hills. 68 rooms and suites, a Michelin-starred restaurant, a wine cellar, hot air balloons, pools, and a spa.📍 Località Monastero d’Ombrone, Castelnuovo Berardenga, Siena🌐 castelmonastero.com

San Domenico Palace, Taormina — A Four Seasons Hotel (setting of White Lotus Season 2)A 14th-century Dominican convent above the Ionian Sea. The original 16th-century cloister is still intact at the heart of the hotel.📍 Piazza San Domenico 5, Taormina, Sicily🌐 fourseasons.com/taormina

If you are booking a 5-star hotel, use my advisor network for your reservation and receive perks and upgrades. I earn a 5% commission on your stay. Once you create an account with Classic Travel linked to my advisor account, you can use the same portal to book 5-star hotels anywhere in the world and receive the same benefits.

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Borgo San Gregorio (for visiting Goleto Abbey — Irpinia, Campania)A wine resort and restaurant in Sorbo Serpico, in the heart of Irpinia, set on the estate of Feudi di San Gregorio winery. 12 rooms with panoramic views of the Irpinian hills, surrounded by vineyards producing Taurasi, Fiano, and Greco di Tufo. Chef Danilo Uva serves traditional Campanian cuisine. About 30 minutes from Goleto Abbey.📍 Località Cerza Grossa snc, Sorbo Serpico (Avellino)🌐 borgosangregorio.com

Santa Chiara Boutique Hotel (Naples)A 4-star boutique hotel right on Spaccanapoli, steps from Santa Chiara and San Domenico Maggiore. An ideal base for this entire episode’s Naples itinerary.📍 Via Benedetto Croce 23, Naples🌐 santachiarahotel.com

🏛️ PLACES TO VISIT

Santa Chiara — Cloister, Museum & Basilica (Naples)The church is free. The majolica cloister and museum (including the Roman baths) cost €6. Open daily 9:30 am–5:30 pm.📍 Via Santa Chiara 49c, Naples📞 +39 081 551 6673🌐 monasterodisantachiara.eu

San Domenico Maggiore (Naples)Church is free and open daily, 10 am–6pm (closed for lunch, 1:30–2:30 pm, weekdays). The monastery visit — including St. Thomas’s cell, his arm bone reliquary, and the sacristy with the royal tombs — costs approximately €10 and is accessed separately. Check hours in advance as they vary.📍 Piazza San Domenico Maggiore 8A, Naples📞 +39 333 863 8997

Abbazia del Goleto (near Sant’Angelo dei Lombardi, Avellino — Irpinia)A Benedictine abbey founded in 1114, now a magnificent roofless Gothic ruin set in a meadow in the Irpinian hills. Free to visit; the grounds are managed by the local community. Check locally for current access, as hours are informal. About 1.5 hours from Naples. Best combined with a stay at Borgo San Gregorio and a meal at Antica Trattoria di Pietro.📍 Sant’Angelo dei Lombardi, Province of Avellino

Certosa di San Lorenzo, Padula (the largest monastery in Italy)Open Wednesday–Monday, 9:00 am–7:30 pm. Closed Tuesdays. Admission €6, reduced €2 for ages 18–25, free under 18. Campania ArteCard accepted. Allow at least 2 hours.📍 Viale Certosa, Padula (Salerno)📞 +39 0975 77552

Pinacoteca di Brera (Milan)Open Tuesday–Sunday, 8:30 am–7:15 pm. Closed Mondays. Admission €20; reduced €4 for ages 18–25; free under 18. Free first Sunday of every month (reservation required). Book at brerabooking.org. Metro: M2 Lanza stop.📍 Via Brera 28, Milan📞 +39 02 72105 141🌐 pinacotecabrera.org

🍽️ WHERE TO EAT

Andrea Pansa (Amalfi)In business since 1830, right on the cathedral square. Order the Santa Rosa sfogliatella — the original, with the amarena cherry in the center. Open daily 7:30 am–11:00 pm.📍 Piazza Duomo 40, Amalfi📞 +39 089 871 065

La Locanda dei Trecento (Padula)Traditional Cilento cooking. Eat before 2 pm, or the town closes until dinner. Open Thursday–Tuesday 11:30 am–late. Closed Wednesdays.📍 Via Annunziata, Padula📞 +39 0975 77680

Antica Trattoria di Pietro (Melito Irpino, Avellino — for visiting Goleto Abbey)In business since 1934, now in its fourth generation. Slow Food Osterie d’Italia award-winner for best regional Italian cuisine. This is the kind of place where Italian-American visitors have been known to cry at the table because the food tastes like their grandmother’s kitchen. Traditional Irpinian cooking — handmade pasta, cured meats, local cheeses, wood-fired focaccia, and Aglianico from the family’s own vines. Closed Wednesdays and two weeks in September.📍 Corso Italia 8, Melito Irpino (Avellino)📞 +39 0825 472010

Are you thinking about a trip to Italy and need help getting started or refining your plan? Book a one-hour consultation, my specialty, and let me help you ensure it’s the best trip possible.

Among my favorite trips to plan are multigenerational family trips — especially when they involve a roots-finding day for those with Italian ancestry. But really, the reason I enjoy planning these so much is that I know how much value I can offer. There are so many things you don’t know that you don’t know, because planning one of these trips is genuinely not easy.

Everyone is excited. Everyone has a different film running in their head. The boomers want Dolce Vita — the café, the piazza, the slow lunch. The Gen X/Millenial parent dreams of wandering like Before Sunrise, unscheduled and open. The grandkids want Pisa for TikTok. Everyone thinks their version of Italy is the best one. The gap between the fantasy and the logistics nobody discussed is what this episode is about.

The weight lands in the middle

The first thing I want to name is something nobody says out loud. When grandparents offer to pay for a significant portion of the trip, it feels like a gift — and it is —, but it also creates an invisible obligation. Now, the Gen X or millennial in the middle is responsible for making sure the investment pays off. Grandma needs to be comfortable. The kids need to be engaged. The teenager needs wifi. The eighty-year-old needs to sit down every twenty minutes. And somewhere in there, the person holding all of this together needs to have something that resembles a vacation.

This is not a complaint about multigenerational travel. It’s an honest description of the dynamics so that the middle generation can go in with their eyes open and build a trip that accounts for what’s actually going to happen — not just what everyone imagines will happen.

Before you book anything, do this

Have the bucket list conversation — but do it properly. Not “what do you want to see?” which produces a list of everything, or more commonly, a big uuuuuh, I dunno. Limit the options by raising the stakes: if you get to choose only one thing on this trip — the Colosseum or the Vatican — which one? Give people time to actually think. Let them sit with it for a few days. What comes back will surprise you. The grandparent who you assumed wanted the Vatican might actually want to see the Forum because her father talked about Rome his whole life, and that’s what he described. The teenager who you assumed wanted Instagram content might actually be obsessed with gladiators. You don’t know until you ask the right question.

The purpose of this exercise is not to eliminate destinations. It’s to identify the two or three experiences that each person would be devastated to miss — and protect those ruthlessly — while letting everything else be negotiable.

Keep it simple: two locations, not three

Do not pack in many locations. Seriously, two locations instead of three for a ten-day trip is plenty. I understand that you want to maximize the experience — you’ve spent all this money to fly across the ocean — but I’m thinking about how many times you need to get to and from a train station, all the bathroom trips the grandparents and the little ones are going to need while you’re trying to figure out what track your train is on, and getting taxis on either side that usually only fit four people. Your time is better spent people-watching in a piazza, trust me.

If you’re choosing between Florence, Venice, and Rome, eliminate Venice. The narrow streets and difficulty getting a quick taxi when you need one can make the trip heavier than necessary.

The Pisa problem

All the Gen Zs will say they want to go to Pisa. It’s purely for TikTok. And here’s the honest truth: Pisa is an entire day trip that won’t deliver much beyond the photo. You’re not eliminating TikTok moments from the trip — you’re not a monster — but you are being strategic about which ones are worth a full day and which ones can be woven into something you’re already doing. The leaning tower is a destination. A beautiful doorway in Florence or a terrazzo floor in Naples is a TikTok moment that happens on the way to something else. Let the kids find those. They will find them. Ludovica in Naples is the perfect example — she was finding restaurants with lines around the block that nobody had heard of, not because she was Italian but because she’s 16 and online.

Give them one meal to find entirely on their own. Let them navigate one afternoon. Two things will happen: they’ll find something surprising, and they’ll feel like participants rather than passengers, which is what makes teenagers tolerable on group trips.

Do not rent a villa

This is the most counterintuitive piece of advice I have, and it’s going to stop people mid-listen. The villa seems perfect. It seems cost-effective. It seems like everyone has space and the setting is beautiful, and you’ll have long lunches on a terrace. You’re dreaming about drinking a glass of wine by the pool, napping in a hammock, gazing at the rolling hills of Tuscany. You’re not thinking about who gets stuck doing all the driving, how many rental cars you’ll actually need, sharing a bathroom with people you don’t normally share bathrooms with, who is going to make breakfast every morning, who is going to go grocery shopping for the coffee and breakfast foods, who is going to be picking up towels, or who thinks the A/C isn’t strong enough and wants to call the owner — but oh wait, you call, you have the number, and you took Spanish in high school, right? Yeah, Spanish is not just like Italian. You know why hotels cost more? Because they head off a million little annoyances.

What it actually means is that the person in the middle is now doing the driving, grocery shopping, morning coffee, meal planning, and activity coordination — on top of everything they were already doing. The villa removes all the infrastructure that actually gives the middle generation a moment to breathe.

The alternative: a large apartment in a city. Florence, or even the outskirts of Florence, where you can walk or take a short train into the center. Here’s what that buys the middle generation — the ability to walk out the door, find a piazza, sit in a café, have a glass of wine, and exist alone for forty-five minutes. That is not a luxury. That is the thing that makes the difference between coming home restored and coming home more depleted than when you left. No matter how loving and well-intentioned everyone in the group is, the middle generation will need that exit. Build it into the trip’s structure before you go.

On the ground: how to structure each day

The toughest part about traveling with an older generation is that people aren’t always honest about their limits — and sometimes they’re not honest with themselves. Or they get confronted with those limitations for the first time on the trip. Walking around a suburban neighborhood every day is very different from traversing cobblestone streets in humid Rome.

This is why I recommend booking one activity everyone does together each day, and then leaving time for people to do things on their own. A private tour solves a lot of problems. You’ll have a guide to lead the way, a local person to ask questions of, skip-the-line tickets already taken care of, and a shared experience that everyone will inevitably process differently — and talking about it later becomes an experience unto itself. Then leave the second half of the day open. Take in more history, shop, park yourself in a piazza and gelato the afternoon away.

For dinner, reservations are a must in the most popular destinations — there’s a lot of very mediocre, if not downright bad, food in the most touristy places. For a big group you’ll need to plan ahead. You can make reservations directly through the restaurant’s website or through thefork.it. One meal together per day — a lunch or a dinner — and then leave people to do their own thing.

When to call a professional

If you want everything planned — drivers, restaurant reservations, guided tours across multiple cities — I strongly urge you to book through a professional. The value you’ll receive, especially when amortized across all the people and problems in the group that are easily mitigated, is tremendous. We just had a family return from a multigenerational trip to Sicily: roots day, city and countryside stays, daily guided tours, van rides between cities, and restaurant reservations for lunch and dinner every day. For a pro, this is easy. For the DIY traveler, plan to take a sabbatical from work to get it done.

So if you’re DIY-ing it: keep it simple. One tour a day, one meal a day, and basta.

The reframe

A multigenerational trip to Italy is one of the most meaningful things a family can do. It is also very complicated in ways that nobody who hasn’t done it will warn you about. Going in with clear eyes about the dynamics, the logistics, and the invisible labor does not diminish the experience — it protects it. The families who have a terrible time are almost always the ones who planned the fantasy and ignored the logistics. The ones who have a transformative time are the ones who planned both.

If you’re in the middle of planning a multigenerational trip to Italy and want someone to pressure-test it before you go, that’s exactly what a one-hour consultation is for. I’ve seen what works and what doesn’t. If you’re a committed DIY-er, I also offer Customized Itinerary Design, where I go much deeper than best advice and actually plan the day-by-day — but you make the bookings. And if you want to turn it over to Arianna and me to just handle it, make an appointment for a free Bespoke Trip Planning consultation, where I’ll be able to give you a price estimate once I know more about your ideal trip.