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
Check out my favorite travel gear and my Etsy shop!
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
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

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