Travel Inspiration from the Chicago Travel & Adventure Show

We attended the Chicago Travel & Adventure Show and heard from some of the most respected voices in travel. Here are the ideas that stuck with us.

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Seek Out “B-Side” Destinations

Travel expert Samantha Brown encouraged travelers to look beyond Europe’s most famous cities.

Instead of only visiting places like Venice or Florence, consider nearby destinations that offer incredible culture with fewer crowds—like Bologna or Modena in Italy.

These “B-side” cities often deliver deeper, more authentic travel experiences.

Is Route 66 the Most Iconic American Road Trip?

With the 100th anniversary of Route 66 in 2026, several speakers highlighted it as one of the most meaningful road trips in the United States.

Rather than rushing from Chicago to Santa Monica, consider tackling the route in segments and exploring the small towns and stories along the way.

Travel Like a Local

Travel writer Jen Ruiz shared how her travels changed when she started staying with local families.

Homestays and local connections can transform a trip from sightseeing into cultural immersion—offering experiences that are nearly impossible to replicate in traditional hotels.

A Simple Way to Give Back While Traveling

One initiative we learned about was Pack for a Purpose, which allows travelers to bring requested supplies to communities they visit.

It’s a small way to create a positive impact while traveling.

Smart Travel Planning Tips

Pauline Frommer shared several practical strategies that can help travelers save money and plan smarter.

When to Book Flights

According to their research:

That timing can sometimes save travelers hundreds compared to booking many months in advance.

Gateway Hopping

Another strategy is flying into a major hub city and then connecting onward on a budget airline.

For example:

This approach can dramatically reduce airfare costs.

Chicago Highlights from the Trip

A Classic Chicago Steakhouse

One of our favorite experiences was dinner at Gene & Georgetti, a legendary Chicago steakhouse known for its old-school atmosphere and incredible steaks.

If you love classic steakhouses, this one is worth the splurge.

Chicago Deep Dish Pizza

We continued our unofficial mission to try Chicago’s most famous deep-dish pizza spots.

This trip’s stop: Lou Malnati’s, a Chicago favorite known for its buttery crust.

A World-Class Tiki Bar

We also returned to Three Dots and a Dash, one of the most famous tiki bars in the world.

If you visit, make a reservation—this place fills up fast.

Key Takeaways

Some of our biggest travel lessons from the show:

A long weekend escape to Toronto that somehow included a cheese-wheel pasta moment, a winter-friendly “walk indoors” downtown route, a surprise winery day trip, and (of course) a tiki bar stop.

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Ashleigh and Christopher recap their February getaway to Toronto, including where they stayed, what they ate, the best sights for a cold-weather trip, and a side quest to Niagara-on-the-Lake for wine tasting—plus a final stop for iconic Windsor-style pizza on the way home.

Where we stayed

One King West Hotel & Residence (near the line between the Financial District and Old Town)

Why we loved it: great amenities (breakfast/coffee, bar/restaurant, fitness center, spa) and an ideal, walkable location

Getting there

Originally planned to take the train, but price jumped—driving ended up being the better deal

Having a car also made the day trip possible

Best meal of the weekend

Sal’s Pasta & Chops (Little Italy)

The showstopper: tableside pasta tossed in a Parmesan wheel (yes, a literal cheese “mixing bowl”)

Also: fried artichokes—and lots of extra cheese on top

Tourist day: downtown classics

CN Tower

Go early for lighter crowds

We paid extra for the higher observation deck

Fun fact: the tower’s origin story is tied to broadcasting/antenna needs as Toronto’s buildings got taller

Ripley’s Aquarium

Busy on the holiday weekend (so many kids!)

The moving walkway exhibit made it much easier to see sharks, stingrays, turtles, and big fish even when crowded

Market lunch

St. Lawrence Market for sandwiches + pastéis de nata

Note to future travelers: we learned the hard way it’s not open on Monday (plan accordingly)

Valentine’s dinner curveball

A reservation got canceled without explanation, so we pivoted to The Carbon Bar

Barbecue Place with multi-course menu options

Day trip: Niagara-on-the-Lake

A chance to finally explore one of Canada’s most famous wine areas

Wineries we visited:

Tawse (Burgundy-focused, standout tasting—so good we brought bottles home)

Ravine (beautiful property, tasting room + restaurant, great for a longer lunch-style stop)

Lunch: The Olde Angel Inn (historic vibes + a little ghost lore)

Strolling the town: coffee, shops, and lots of “we need to come back” energy

Tiki stop

Shameful Tiki Room

Lounge seating, strong drinks, and a mystery bowl that comes with a gong moment

Food is more snacky—good to know before you go

Last morning: Hockey Hall of Fame

A must for hockey fans (and surprisingly exciting even if you’re just nostalgic for the Red Wings era)

Seeing the Stanley Cup + classic jerseys, gear, and trophies

Great exhibits, including women in hockey, plus interactive stations (shooting pucks, etc.)

Final food mission: Windsor pizza

We crossed to Windsor specifically to try it

What makes it “Windsor-style”: distinctive shredded cheese, pepperoni cut into strips, and the classic canned mushroom vibe

Pro tip: if you’re heading back across the border right after, consider ordering smaller than you think

Bonus travel tip

Windsor can be shockingly affordable for hotels compared to Detroit—worth considering if you have a passport and don’t mind the border logistics.

A last-minute holiday trip turned into one of our favorite Puerto Rico itineraries yet. This was our fifth visit to the island, and instead of trying to see everything, we split the trip between Old San Juan and Santurce, rented a car only when it made sense, and focused on the experiences we genuinely love repeating.

In this episode, we share the practical decisions that made this trip work, what we’d do differently next time, and the places we keep returning to — from winter baseball and rum tours to beach days, food favorites, and one surprisingly great seasonal fast-food discovery.

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Old San Juan

Santurce

Instead of renting directly at the airport, we took a short Uber ride to an off-airport rental location and saved a significant amount of money. This strategy works in many destinations, not just Puerto Rico.

Paseo de la Princesa Christmas Lights

Rum Walking Tour

Carly’s Fine Bistro

La Factoría

If you want to visit Bacardí while staying in Old San Juan, the ferry provides an easy and scenic route across the bay.

One of the most unexpectedly fun nights of the trip.

Even if you are not a huge baseball fan, this is a great cultural experience.

La Placita

Museo de Arte de Puerto Rico

Sunset Salsa Class at Ocean Park Beach

Mount Britton Trail

We also saw progress being made on trails closed since Hurricane Maria, which was encouraging.

Why we love it:

El Viejo Almacén

Orabori Empanadas

Cafetería Mallorca

El Vino Crudo

Chocobar Cortés

La Madre

Café Cola’o

Barista Squared

Cayo Blanco

Seasonal Coquito Frosty

We opened a 2018 Bordeaux purchased for around $15 and aged at home. After several years, it drank like a much more expensive bottle. A simple storage space and tracking app can make aging wine accessible and affordable.

Old San Juan

Puerto Rico works extremely well when you:

Full itineraries, planning notes, and bonus travel resources are available through supporter tiers at:

January 2026 Travel News: New Routes, Smoother Airports, and What Actually Matters This Year

A new year brings big shifts across the travel world — and in this episode, we break down what’s actually worth paying attention to as you plan trips for 2026.

From major airline route expansions and new nonstop options to Hawaii and the Caribbean, to changes that could quietly improve (or complicate) your airport experience, we cover the developments that impact real travelers — not just industry headlines.

You’ll hear about:

Airline mergers in Mexico and what they could mean for low-cost travel

American Airlines’ 100th anniversary expansion and why Chicago flyers should care

New nonstop routes to Hawaii and emerging Caribbean destinations

Which airlines and airports are actually on time — and which are the most stressful in the world

TSA’s expanding touchless ID program and how it could speed up security

Cruise news, including a luxury line going adults-only

New museum pricing in Europe and what travelers should expect

A surprising new visa-free destination opening up to Americans in Central Asia

If you like staying informed, planning ahead, and making smarter travel decisions without obsessing over every headline, this episode gives you a clear, grounded snapshot of where travel is headed in early 2026.

A Year of Going Deeper: Our 2025 Travel Recap

In this end-of-year episode, we sit down to recap our 2025 travels — not as a highlight reel, but as a reflection on how we travel, why our preferences are changing, and what we’re carrying forward into the next year.

Puerto Rico (New Year’s) — navigating island infrastructure realities and adapting plans on the fly

Chicago — the Travel & Adventure Show, favorite neighborhoods, and standout food

Mexico City — private guiding, home cooking, and a trip that permanently raised our expectations

Traverse City, Michigan — spring camping, fall wine country, and a destination Thanksgiving

Watkins Glen & the Finger Lakes — camping, hiking, and cool-climate wine

New Orleans — one of the best food cities in the world

Summer Camping Road Trip (3 weeks)

Bruce Peninsula National Park

Algonquin Provincial Park

Montreal

Acadia National Park

Connecticut & Rhode Island

Scranton, Pennsylvania

Michigan Favorites — Ludington State Park, the Straits, Fayette, and Detroit day trips

Why private and small-format experiences consistently outperform big group tours

How long weekends can deliver outsized value with less burnout

The tradeoffs of camper travel — and when it shines vs. when it’s hard

Food as a decision-maker: Mexico City and New Orleans set the bar

Returning to places at different life moments — and why that matters

Learning to travel well without always flying far

Michigan wine discoveries and joining another wine club

Standout meals in Mexico City and New Orleans

Unexpected gems in Detroit’s food scene

Cooking Thanksgiving away from home — and why we’d do it again

This isn’t just a recap of where we went — it’s about how our travel philosophy continues to shift:

Less checklist travel

More flexibility and context

Fewer crowds, better conversations

Trips that fit real life, not the other way around

As we look ahead to 2026, we talk about what we miss, what we don’t, and why traveling thoughtfully continues to matter more than ever.

December 2025 Travel News

Christopher and Ashleigh guide you through December’s most practical travel updates, from shifting airline routes to festive European destinations, with their trademark blend of honest insight and flexible planning tips.

This episode’s wine break skips the glass and instead offers practical gift-giving tips. Christopher and Ashleigh suggest picking wines adjacent to the recipient’s favorites (think French Chardonnay for an American Chardonnay fan) and recommend seeking advice from knowledgeable staff at local wine shops or large retailers like Total Wine. If you’re unsure of someone’s preferences, a little insight into whether they enjoy drier or sweeter wines can go a long way.

Tune in for a practical, up-to-date roundup to help shape your next adventure. Listen to the Go See Do Explore Podcast for honest travel news and tips to make your trips more meaningful—and a little more spontaneous.

Travel Trends 2026: Skyscanner’s Surprising Predictions & Value Destinations

Christopher and Ashleigh are your guides this episode as they dig into Skyscanner’s forward-looking report on how—and where—we’ll be traveling in 2026. They break down emerging trends, highlight offbeat and best-value destinations, and share honest perspectives on what might actually shape your future trips. To read the full report, click here.

The conversation kicks off with some genuinely unexpected trends Skyscanner is forecasting:

Midway through, the hosts pause for a wine break, sampling Mary Taylor Manchuela from Spain—an earthy, high-acidity red that’s bolder and more tannic than last week’s Portuguese pick. Christopher encourages listeners to discover collections of regional wines as a way to extend the travel experience at home.

Returning to trending and value destinations, Christopher and Ashleigh share specifics from the Skyscanner data:

Looking ahead, the hosts note that travelers are becoming more conscientious—seeking quieter places, considering curated experiences, and expecting tech like AI to make the journey more seamless. The report predicts most people will travel as much or more in 2026, with many planning multi-city trips and investing more in flights and hotels.

For honest, practical inspiration on how global travel trends might shape your next adventure, listen in to this episode of the Go See Do Explore Podcast.

Airports Without Stress: Practical Tips for a Better Travel Day

Christopher and Ashleigh share their favorite strategies for turning the airport from a dreaded obstacle into a surprisingly enjoyable part of your travels. Drawing on their own experiences and a mindset shift, they offer concrete ways to minimize stress, stay flexible, and even discover small pleasures along the way.

From booking smarter to making the most of your time before takeoff, the episode covers practical steps that help you avoid common headaches and find value—no matter where you’re flying. Christopher and Ashleigh emphasize treating the airport as part of the journey, not just a hurdle, and share tips for navigating both the expected and the unexpected.

On this episode’s wine break, the hosts sample Mary Taylor Douro, a rich, full-bodied Portuguese red from the historic Douro region—perfect for reflecting on travel’s unexpected joys.

The conversation continues with tech tips (portable chargers are a must), airport research hacks (check Eater guides for the best terminal eats), and why TSA PreCheck is a worthwhile investment if you fly even once a year. Ashleigh highlights the value of having backup flight plans and knowing what to expect at your layover airports. The hosts also reminisce about memorable terminals, like Detroit’s bright McNamara, San Francisco’s mid-century modern lounge, and the rocking chairs in Charlotte.

Whether you’re a reluctant flyer or secretly love airports, this episode of the Go See Do Explore Podcast is packed with honest, actionable advice for making your next travel day more enjoyable. Tune in and discover how a few smart tweaks can help you go, see, do, and explore with less stress and more delight.

Travel Mistakes We’ve Actually Made- And How to Avoid Them

Christopher and Ashleigh share honest stories about their own travel missteps—so you don’t have to learn the hard way. This episode is packed with practical lessons, from booking blunders to overambitious itineraries, all with the goal of helping you plan smarter and travel happier.

From wrong hotels in Manhattan to misaligned flights and rental cars in Puerto Rico, the hosts open up about mistakes that even seasoned travelers make—plus the simple systems and mindset shifts that help them recover (and sometimes even laugh about it later).

Mid-episode, Christopher introduces a cozy wine break: mulled wine using Cherry Wine (a semi-sweet wine from Good Harbor on Michigan’s Leelanau Peninsula) and their favorite mulling spices from the Spice House in Chicago—a small moment of comfort amid the chaos of travel stories.

Whether you’re a careful planner or a spontaneous explorer, you’ll find real, actionable advice in this episode. Listen in for relatable mishaps, practical fixes, and the kind of honest perspective that makes the Go See Do Explore Podcast a trusted travel companion.

Top 10 Michigan Christmas Experiences: Light Shows, Markets & More

Christopher and Ashleigh share their favorite ways to make the most of Michigan during the Christmas season, curating a list that blends festive classics with offbeat finds for a memorable holiday adventure. Here is a rundown of what they discuss:

Midway, the hosts pause to share a wine break: last night’s discovery of a Lebanese red blend at a Middle Eastern restaurant. Christopher notes how rare it is to find Middle Eastern wines in the US, describing the blend as “nice and fruity and acidic,” despite some sediment. It’s a reminder that travel—and holiday outings—can bring unexpected surprises close to home.

Whether you’re looking for cozy markets, outdoor adventure, or new traditions, this episode is packed with honest, practical tips for enjoying Michigan’s holiday season. Tune in to the Go See Do Explore Podcast for thoughtful guidance, festive inspiration, and plenty of ideas to make your Christmas in Michigan truly memorable.