The Travel Between

10/25/2026

Happy Mother-in-Law Day. If you've ever tried traveling with your in-laws, this one's for you.

Traveling with in-laws can be one of the best trips your family ever takes. It also goes more smoothly when a few things are agreed on before anyone packs.

Here's the peace treaty I'd suggest:

Article 1: Everyone gets a door that closes.
Article 2: One anchor activity a day, and she picks day two.
Article 3: The 1 to 3pm rest window is sacred, for every generation.
Article 4: Each couple gets one outing on their own.

None of it is about keeping people apart. It's about making sure everyone has enough room to enjoy being together.

Tag the mother-in-law who'd sign this. Or the one who'd add an Article 5.

10/23/2026

The best Hawaiian island for families with grandparents isn't always the obvious one, and there's one I'd usually skip.

Hawaii feels like the dream multigenerational trip, and it often is. But each island is a different trip. How much driving you'll do, how much walking is involved and what the terrain is like matter more than which beach has the prettiest photos.

Then there's what the tourism sites don't mention: accessibility details that can make or break a trip with a parent who uses a cane or a wheelchair.

I compared the islands for three-generation families, including the one I'd steer most families away from and why.

Read it here: [URL]

Which island is your family dreaming about?

10/22/2026

The best all-inclusive resorts for multigenerational families pass one test: would it work for a 3-year-old AND a 73-year-old?

All-inclusives sound like the easy answer for three generations, and they can be. But a lot of resorts are wonderful for one generation and hard on another.

Some look perfect for kids until Grandpa has to walk a quarter mile to dinner. Others are beautiful and peaceful, with nothing for a toddler to do before 9am.

When I look at a resort for a multigenerational family, I check how far everything is from the rooms, how you get into the pool, what ages the kids' club takes, how dinner reservations work and how the rooms can be set up.

Are you an all-inclusive family, or do you like to explore on your own? Tell me below.

10/21/2026

Wondering when to book holiday travel for a big family? Here are the trips I'm booking for families right now, and why waiting costs big families more than anyone else.

When you travel with three generations, you need more of the things that go first: connecting rooms, accessible rooms and enough seats together on the same flight. A couple can be flexible. A family of nine usually can't.

Right now I'm helping families plan for:

• Thanksgiving
• Winter break
• Spring break 2027
• Christmas market river cruises
• The August 2, 2027 total solar eclipse in Spain

I know prices are up, and a lot of families are trimming their plans so they can pay trips off sooner. Booking earlier can help with that too, because it can mean more time to pay, where payment plans allow.

If one of these is on your family's list, tell me about it here:

https://f.mtr.cool/nawl3p03ji

10/19/2026

If everyone's cranky by day three of your multigenerational trip, it's probably not your family. It's the itinerary.

I see it all the time. A beautiful plan with five things a day, built with love, because you want everyone to see it all. Then the kids are overstimulated, the grandparents are worn out and you've become the cruise director nobody asked for.

So I plan every multigenerational trip with the One-Activity Rule: one anchor activity per day. One thing that matters. Everything else is optional.

It sounds like doing less. It's actually how you get more of what you came for. The kids get time to just play. The grandparents can rest without feeling like they're holding everyone back. And the thing you did do, everyone remembers.

What's the one activity you'd keep if you could only pick one per day?

10/18/2026

Packing for a family trip with grandparents? Every family has one person who packs for every possible scenario. Who is it in yours?

In a lot of families, it's Grandma. The extra sweater, the full first-aid kit, snacks for a flight that serves snacks, an umbrella for a beach trip. And honestly? Sometimes she's right, and she's the hero of the trip.

But when you're packing for three generations, every extra pound adds up. More bags to check, more bags to carry and more to keep track of in an airport with a toddler on your hip.

The rule I live by: pack for the trip you're actually taking, not the one you're worried about.

Tag the family member who'd bring a suitcase just for snacks.

10/16/2026

An Ireland road trip with seniors is on a lot of family bucket lists, especially for tracing your roots. The pacing is what makes or breaks it.

Ireland looks small on a map, and that's the trap. Roads are narrow and winding, castle stairs are steep and a day that looks easy on paper can wear older travelers out by lunch.

The families who come home happiest don't try to see everything. They keep drives manageable, book the things that sell out ahead of time and choose places to stay where Grandma isn't facing three flights of stone steps at the end of the day.

I wrote a full guide to an Ireland road trip with seniors: how to pace it, what to pre-book and which castle stays are actually accessible.

Read it here: [URL]

Is Ireland on your family's list? Tell me who you'd bring.

10/15/2026

PreCheck vs Global Entry vs CLEAR: if you're flying with kids and grandparents this holiday season, read this before you pay for any of them.

PreCheck, Global Entry and CLEAR all promise a faster trip through the airport, and they're not interchangeable. For a family traveling across three generations, the right choice depends on how often you fly, whether you're leaving the country and who's in your group.

Holiday security lines are stressful enough on your own. Add a stroller, a car seat, a carry-on full of snacks and a parent who needs to sit down, and every minute in that line feels longer.

I put together a side-by-side comparison of who each program is for, written with your whole family in mind, so you can decide once and stop second-guessing it.

Read it here: [URL]

10/14/2026

The problem cruising solves that no land destination fully solves: everyone is cared for, and nobody has to be the one managing it. Certified kids' clubs, enrichment programming for grandparents, real downtime for parents. Here's why it's one of my top 8 picks for 2026.

The Ultimate List of Classic Family Vacation Destinations for 2026 Disclosure: This post may contain affiliate links. I only recommend partners I personally trust for multi-generational family travel. If you book through one of my recommended partners, I may earn a small commission at no extra cost....

10/14/2026

Planning a trip with grandparents? Before you book anything, ask your parents these five questions.

We plan around the kids because their needs are loud. The grandparents' needs tend to show up later, usually on day two, when the stairs or the heat catch up with them.

October is Family History Month, so here's a conversation worth having before anyone books anything:

1. Where have you always wanted to go?
2. What wears you out fastest: stairs, heat, long walks or early mornings?
3. What time of day do you feel your best?
4. What would you happily skip?
5. Which trip from your childhood do you still remember?

That last one is my favorite. Sometimes the answer becomes the whole trip. Sometimes it's a story your kids get to hear for the first time. Either way, it's worth asking.

Share this with your family, or save it for your next visit home.