Family Travel Unpacked: Make the Most of Travel With Kids

Is it worth taking your kids back to a vacation destination you've already visited? In this episode, I share why repeat family trips are often the smarter move, especially for multigenerational travel, plus the honest downsides and how to make a return trip to Costa Rica, Hawaii, Italy, Alaska, Puerto Rico, or Amsterdam feel brand new.

Every family trip we have planned for the next six months is a repeat destination: Miami, New York, Costa Rica, a mystery state, and Amsterdam and Paris. In this episode, I explain why that's not a rut. Going back lets you scout logistics for a big group, explore new regions, see a place through older kids' eyes, and travel with a lot less planning stress.

In this episode:

• Why I scout destinations with just the four of us before planning winter break for our extended family of about 13
• Lessons from Riviera Maya, Hawaii, and Costa Rica: group transportation, restaurant reservations, accessible hotels, pacing, drive times, and car-sickness routes
• Going deeper on a return visit: Rome versus the Dolomites in Italy, three very different Alaska trips, and two Puerto Rico trips that felt like different destinations
• Amsterdam with a newborn and a toddler versus Amsterdam with two teens
• How familiarity makes family travel easier, including knowing where to find Celiac-safe, gluten-free food
• The downsides of repeat vacations: less novelty, limited school breaks, changed expectations, and why Celiac would make a return trip to Japan harder
• Questions to ask before choosing a new destination or a return trip
• Simple ways to make a repeat trip feel fresh

Timestamps

• 00:00 — Every trip is a repeat
• 02:00 — Why go back?
• 02:36 — Scouting for big groups
• 07:48 — Going deeper
• 11:56 — Same place, older kids
• 14:44 — The comfort of familiarity
• 16:47 — The downsides
• 21:02 — New or return?
• 21:55 — Making it feel fresh
• 23:59 — Wrap-up

Related Episodes

• S1 Ep. 45 — Alaska With Kids: Anchorage Edition with My Teen
• S1 Ep. 35 — From Tot to Teen: How Travel With Kids Changes Through the Stages
• S1 Ep. 37 — Portugal with Kids: Itinerary, Tips and My Honest Take
• S2 Ep. 2 — London with Kids
• S2 Ep. 5 — Azores with Kids: The Full São Miguel Guide
• Hawaii vs Costa Rica: Showdown in Paradise
• Dolomites With Kids: What Families Need to Know
• Making Multi-Generational Travel Work for Everyone
• Celiac Travel Tips for Families

Destination Guides

• Costa Rica travel planning
• Hawaii travel planning
• Where to stay on Oahu
• Best resorts in Riviera Maya for families
• Summer Northern Italy itinerary + recap
• Alaska travel planning hub
• Puerto Rico with kids
• Things to do in Miami with kids
• NYC attractions for kids

Points & Miles

• Best credit cards for family travel

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

Blog The Family Voyage

Get your free ebook The Busy Mom's Guide to Free Travel

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Chase Sapphire credit cards

What apps and websites make planning a family trip with points and miles easier? In this episode, I walk through the exact tools I use for every trip, from finding award seats and nonstop routes to organizing the itinerary and getting through travel day with kids.

It started with a mistake. This morning I discovered I'd booked a return flight a full month too late, and a tool I've had for almost 20 years would have caught it. So here's my whole toolkit, in the order I use it, including the ones I should be using more.

In this episode:

• Why Thrifty Traveler Premium's deal alerts and credit card benefit tracker are worth the subscription
• My backwards search trick on FlightsFrom to find nonstop gateways from any destination
• How I use PointsYeah, PointsPath Pro, and seats.aero to find award seats, plus the programs PointsYeah is missing
• Why you should always confirm award space with the airline before transferring points
• The Google Sheets layout I use to build every itinerary, plus the shared doc that stores all our loyalty numbers
• How TripIt keeps confirmations in one place (and how it would have caught my mistake)
• Where AI fits in my planning, and where it doesn't
• The United, Hilton, and Avis app features that make travel days easier
• The Allyz app from our annual Allianz policy, and when to compare policies on Squaremouth
• Earning extra on tours, rental cars, and cash hotel stays with shopping portals and CardPointers

Deal Alerts & Card Benefits

• Thrifty Traveler Premium (save $20 with code THEFAMILYVOYAGE)

Route Finding

• FlightsFrom
• FlightConnections

Award Search

• PointsYeah
• PointsPath 
• seats.aero 

Trip Organizing

• TripIt 

Travel Insurance

• Squaremouth (compare travel insurance policies)

Shopping Portals & Card Offers

• Rakuten
• TopCashback
• Capital One Shopping
• CardPointers (lifetime plan discount)

From The Family Voyage

• Fall Break Destinations for Families
• Best credit cards for family travel

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

Blog The Family Voyage

Get your free ebook The Busy Mom's Guide to Free Travel

Check out my favorite travel gear and my Etsy shop!

Chase Sapphire credit cards

How many days do you actually need in the Azores with kids, and is São Miguel worth the trip? This is the full São Miguel guide — flights and points, renting a car, where to stay, the best hot springs and waterfalls, whale watching, and the honest story of how our four days actually went, weather included.

We paired this trip with a stop in London (full recap in Season 2, Episode 2), and if you want the complete points and miles breakdown for the whole ten-day trip, that's back in Season 1, Episode 42. This episode is just about São Miguel: what it's like, what to do, where to stay, and what we'd change next time.

In this episode:

• Why the Azores feel nothing like mainland Portugal, even though they're technically part of it
• How long you actually need on São Miguel (we had four days — here's why that wasn't quite enough)
• Best time of year to visit and how the island's microclimates can wreck a tight itinerary
• The points and miles breakdown for getting to and from São Miguel, plus why renting a car is non-negotiable
• Where to stay: the DoubleTree by Hilton in Lagoa on points, plus Pedras do Mar and Senhora da Rosa for cash bookings
• Scenic lookouts, waterfalls, hot springs (including the one that's nearly impossible to book), whale and dolphin watching, and a pineapple farm
• Our actual day-by-day itinerary, weather setbacks and all
• A split family verdict: how Jacob, Shoshana, Ronnie, and Melissa each felt about the island differently

Timestamps

• 00:00 — Intro & Recap of the Trip
• 00:52 — Why the Azores Aren't Mainland Portugal
• 04:03 — How Long You Actually Need
• 06:07 — Best Time of Year to Visit
• 07:16 — Flights, Points & Renting a Car
• 10:50 — Where to Stay on São Miguel
• 13:18 — Best Things to Do
• 20:04 — Our Actual Day-by-Day Itinerary
• 22:39 — Family Verdict & What We'd Change

Links

The Full Guide

• São Miguel, Azores Travel Guide — full write-up with the map, packing list, and activity details mentioned in this episode

Related Episodes

• S1 Ep. 42 — How We Planned London & Azores on Points
• S1 Ep. 49 — London vs. Azores Recap: A Kid's Take
• S2 Ep. 2 — London with Kids: What We Loved, What Surprised Us, and What We'll Do Differently Next Time

Where We Stayed

• DoubleTree by Hilton Lagoa — booked on points, full Hilton transfer math in the guide
• Pedras do Mar Resort & Spa — splurgier north coast pick
• Senhora da Rosa — cash booking, pool table and a pineapple-greenhouse hot tub

Things to Do

• Poça da Dona Beija hot springs
• Caldeira Velha tickets — book the moment your dates are set, slots go fast
• Whale & dolphin watching tour
• SpotAzores live weather cams (São Miguel)

Car Rental

• Discover Cars — São Miguel local rental options

Flight Deals

SAVE $20 on Thrifty Traveler Premium

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

Blog The Family Voyage

Get your free ebook The Busy Mom's Guide to Free Travel

Check out my favorite travel gear and my Etsy shop!

Chase Sapphire credit cards

Is the Chase Sapphire Reserve still worth its $795 annual fee after the 2025 overhaul — and what does the Chase Sapphire Preferred's new 4:3 Hyatt transfer ratio mean for your points? This episode breaks down every change to both Sapphire cards this year, why Melissa upgraded back to the Reserve with no welcome bonus, and exactly how she used Chase's "The Edit" hotel program to book two rooms for four nights in Amsterdam for 100,000 points and fifty dollars.

In this episode:

• What the Chase Sapphire Reserve looked like in 2016 vs. what it costs and covers now
• Why Melissa and her husband downgraded to Freedom Unlimited in 2023 — and why that trick doesn't work anymore
• The Chase Sapphire Preferred's June 2026 overhaul: the Hyatt transfer ratio drop, the doubled hotel credit, and what's grandfathered until October
• Three reasons Melissa upgraded to the $795 Reserve without a welcome bonus
• A full breakdown of The Edit: split reservations, price-matching, and stacking Points Boost to book Amsterdam's Kimpton De Witt for next to nothing
• Why Melissa isn't sure she'll keep chasing Hyatt Globalist status, and what that means for her hotel strategy going forward

Timestamps:

00:00 Welcome
03:15 Chase Sapphire Reserve Refresh
04:51 Chase Sapphire Preferred Refresh
09:08 Why I Upgraded Again
13:16 Chase Travel's The Edit (My Booking Hacks)
18:13 More Resources and Wrap Up

Resources:

• Chase Sapphire Preferred: What's Changing and What You Should Do About It
• 3 Reasons I Upgraded to the Chase Sapphire Reserve (Even Without a Bonus)
• Case Study: The Edit Shines in Amsterdam

Cards mentioned

• Chase Sapphire Reserve / Preferred
• Chase Ink Business Preferred / Sapphire Reserve for Business
• Chase Freedom Unlimited

General resources

• Best Credit Cards for Family Travel
• Free Travel resource page

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

Blog The Family Voyage

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Nine years ago this month, Melissa's family packed up the car and set off on what was supposed to be a one-year adventure — and turned into almost two. In this reflective episode, she looks back at what actually stuck: the deep family bond that full-time travel built, why "owning your happiness" became a lasting family value, and how those lessons still shape the way they travel.

In this episode:

• The 2017 family trip that turned into two years on the road
• The two biggest takeaways from full-time travel — and why neither one is really about travel at all
• How those lessons still show up in how the family plans trips today, even short ones
• Why this isn't a "quit your job" pitch, and small, realistic ways to build in a pause without upending your life

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

Blog The Family Voyage

Get your free ebook The Busy Mom's Guide to Free Travel

Check out my favorite travel gear and my Etsy shop!

Chase Sapphire credit cards

Family travel to London with kids: what we loved, what surprised us, and what we'd do differently on our next trip

We just spent five days in London with the kids, and rather than walk you through a stop-by-stop itinerary (that's what the blog article is for), this episode is the honest debrief: each of our four favorite things from the trip, where we ate, what caught us off guard about the city, and what's already on the list for next time.

IN THIS EPISODE

• Where we stayed near King's Cross and why the location mattered more than the room size
• Each of our four top picks: Harrods, the Tower of London and Changing of the Guard, the Warner Bros. Studio Tour, and two West End/Globe shows
• Where we ate - afternoon tea at the Ampersand, Hobson's Fish & Chips, a 100% gluten-free splurge at Niche, and Mango Indian
• What surprised us about London, good and bad
• What we'd do differently on our next visit

Timestamps

• 00:00 — Introduction
• 02:11 — Getting There & Getting Around
• 04:34 — Where We Stayed
• 07:00 — The Highlights: Our Four Favorite Things
• 15:32 — Food Highlights
• 12:36 — What Surprised Me
• 16:02 — What We'd Do Differently Next Time

Resources

• Our 5 Day London With Kid Itinerary
• Where to Stay in London with Kids on Points (by Program)
• Changing of the Guard guided tour
• Tower of London tickets
• Episode 42 — How We Planned London & Azores on Points 
• Episode 49 — London + Azores: A Kid's Take
• Best Credit Cards for Family Travel  
• Join the newsletter

Coming Soon on the Blog

• Warner Bros. Studio Tour London: Tips & Tricks

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

Blog The Family Voyage

Get your free ebook The Busy Mom's Guide to Free Travel

Check out my favorite travel gear and my Etsy shop!

Chase Sapphire credit cards

Episode Description
My most popular article of the year — now an episode. A region-by-region fall break guide for families, plus four spots that didn't make the original article.

East Coast Fall Break Escapes: New York City · Finger Lakes · Washington DC · Colonial Williamsburg · Philadelphia · Boston · Sarasota · Orlando · Iceland

Midwest Fall Break Favorites: Chicago · Cleveland · Louisville · St. Louis · Aruba & Curaçao

Mountain/West Fall Break Options: Arizona · San Diego · Yosemite · Hawaii  · La Paz, Mexico

Plus: why fall beats spring break and summer for weather, crowds, and price — and how we use points and miles to book most of it without a strict budget.

Season 2 of Family Travel Unpacked starts here. Hit follow so you don't miss what's next.

Timestamps

• 00:00 — Season Two Kickoff
• 01:48 — Why Fall Break Works
• 04:21 — East Coast Fall Break Escapes
• 15:49 — Midwest Fall Break Favorites
• 20:41 — Mountain/West Fall Break Options
• 26:23 — Wrapping Up

Resources

Awesome Fall Break Destinations for Families 

East Coast

• NYC attractions for kids: 
• Finger Lakes with kids
• Watkins Glen hiking tips 
• Best things to do in DC with kids
• Williamsburg, Jamestown & Yorktown itinerary 
• Colonial Williamsburg tips
• Fun things to do in Sarasota with kids
• Orlando with tweens
• Tips for Universal Studios Orlando 
• Best Iceland tours
• Visiting Iceland on a budget 

Midwest

• Louisville weekend itinerary
• Lexington, KY weekend itinerary (Louisville day trip)
• Day trips from Cleveland 
• St. Louis with kids

Mountain/West

• Scottsdale & Phoenix with kids
• 8 great things to do in Arizona with kids
• San Diego with kids 
• Where to stay in San Diego with kids
• Things to do on Oahu with kids
• Things to do on Maui with kids
• Things to do on Kauai with kids
• Big Island 5 Day Itinerary

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

Blog The Family Voyage

Get your free ebook The Busy Mom's Guide to Free Travel

Check out my favorite travel gear and my Etsy shop!

Chase Sapphire credit cards

Our Trip Fell Apart (But Our Points Didn't) — Plus How to Travel for Free with Kids

A Southwest delay killed our Charleston beach trip — but because it was booked on points, we walked away without losing a dime. Here's exactly how we unwound three different award bookings, plus a full breakdown of how to earn and use points to travel with kids for free.

Melissa was supposed to be recapping a family beach getaway to Wild Dunes, a Hyatt resort near Charleston. Instead, a cascading Southwest delay forced a last-minute cancellation — and this episode walks through how to cancel an award flight, an award hotel stay, and a rental car booking without eating the cost. Then it's a deep dive into the credit card and points strategy that makes free family travel possible in the first place.

In This Episode

• How to cancel an award flight and get every point back
• What really happens when you cancel a hotel award stay inside the cancellation window
• Two ways to avoid a last-minute hotel cancellation fee
• Why rental car bookings through travel portals (Capital One, Chase, Priceline) can get complicated
• Why earning points is harder for families than solo travelers
• The fastest way to earn points: credit card sign-up bonuses
• Best starter cards for family travel (Chase Sapphire Preferred, Ink Business)
• How to search and book award flights (Google Flights, PointsYeah, AwardTool, airline alliances)
• What a repositioning flight or drive is, and when it's worth it
• The Southwest Companion Pass strategy for families
• Hotel points strategy for families (Hyatt, IHG, Hilton, Choice)
• Practical tips for booking flights and hotel rooms with kids

Chapters

00:00 Intro & catching up 
01:00 The Wild Dunes trip and the cancellation cascade 
03:00 Unwinding the points: flight, hotel, and rental car 
08:30 Why points are harder to use for families 
09:30 Earning points: sign-up bonuses and transferable points 
13:00 Booking award flights (tools, alliances, repositioning) 
18:30 The Southwest Companion Pass 
20:30 Hotel strategies: Hyatt, IHG, Hilton, Choice 
25:00 Practical tips and wrap-up

Chase Sapphire credit cards
Best Travel Credit Cards for Families
Southwest Companion Pass
Four Reasons I LOVE Award Travel
How to get discounted rental cars
Chase Freedom credit cards
Chase Ink Business credit cards
Capital One Venture X credit card

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

Blog The Family Voyage

Get your free ebook The Busy Mom's Guide to Free Travel

Check out my favorite travel gear and my Etsy shop!

Chase Sapphire credit cards

Planning a weekend trip to Philadelphia? We spent 24 hours in the city using points for flights and a free hotel night, hitting Independence Hall, the Liberty Bell, and some of the best Israeli food in the country.

We flew nonstop on American using Alaska Atmos points, stayed at the Hyatt Centric Rittenhouse Square on a free night certificate, and packed in a museum, three restaurants, and a same-day Independence Hall reservation — all in one night.

In this episode:

• Booking nonstop American flights with Alaska Atmos points (9,000 for first class out, 4,500 for economy home)
• A free night at the Hyatt Centric Rittenhouse Square using a Hyatt credit card certificate
• The Weitzman National Museum of American Jewish History's exhibit on the Jewish merchants who supplied the American Revolution
• Dinner at Zahav, brunch at Dizengoff, and lunch at Goldie — three spots from chef Michael Solomonov's CookNSolo group
• Booking a same-day Independence Hall tour through recreation.gov
• Where past Philly trips with the kids fit in — the Franklin Institute, the Academy of Natural Sciences, and the Museum of the American Revolution

Timestamps (estimated — confirm against final recording before publishing)

00:00 — Intro 
01:15 — How we booked it: Alaska Atmos points 
03:00 — Past Philly trips & who it's for 
04:30 — Weitzman Museum exhibit 
06:00 — Zahav, Dizengoff, and Goldie 
08:00 — Independence Hall in 25 minutes 
09:30 — Liberty Bell and Rittenhouse Square 
11:00 — Hyatt Centric review + outro

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

Blog The Family Voyage

Get your free ebook The Busy Mom's Guide to Free Travel

Check out my favorite travel gear and my Etsy shop!

Chase Sapphire credit cards

Boston with kids doesn't have to mean one long trip — after two separate weekend visits in the same year, here's what's worth doing, where to stay on points, and the one expense that caught us off guard. In this episode 50 recap, I compare two Hyatt Regency stays booked on free night certificates, share the Alaska Atmos points trick that got us into first class for less than economy, and break down where to eat, tour, and skip the rideshare surprise that cost us the most.

In this episode:

• Why we're recapping two different Boston trips — one with our daughter last summer, one solo-parent-turned-family-reunion this year — in a single episode
• Booking first class on American Airlines for just 9,000 Alaska Atmos points each, because airfare spiked and economy award seats disappeared
• Hyatt Regency Boston vs. Hyatt Regency Boston Harbor: same category 4 free night certificate, two completely different trips
• Boston Tea Party Museum and a guided Freedom Trail walking tour — why paying for a guide beat doing it ourselves in our 20s
• The surprise expense
• Getting around Hyatt Regency Boston Harbor without a car: the shuttle, the $2.40 ferry, and why weekends are trickier than weekdays
• Who Boston is best for, from toddlers to a no-kids weekend away

Boston travel resources
Boston Tea Party Ships & Museum
Freedom Trail guided tour 
Duck boat tour
Hyatt Place Boston/Seaport

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

Blog The Family Voyage

Get your free ebook The Busy Mom's Guide to Free Travel

Check out my favorite travel gear and my Etsy shop!

Chase Sapphire credit cards