Hi Reader,

My 2026 has been packed with family events. As in, my sibling turns 40 this year. My mom turns 80 (don’t tell her I told you). My in-laws celebrated their 50th wedding anniversary, my second cousin got married, and my niece graduated high school. Five milestones, one calendar year, and every single one involves some sort of travel.

As you can tell, I come from an enormous family, and we gather often. So, 2026 has turned into an accidental audit of how to handle family travel. We’ve done it every which way. Renting a house together, spreading across hotel rooms, holing up at a single resort.

And my family is hardly an anomaly. Our team sees the same pattern with our clients: families head to Hawaiʻi for spring break, Europe for the summer, California for a road trip, and each trip is a completely different animal.

But underneath it all, the same two questions keep coming up. How do you handle the pace? And how far ahead do you actually need to plan? It’s a lot of logistics, but it’s also kind of a gift. Not every family gets this many excuses to gather in one year.

Plan the Pace, Not Just the Place

Here’s what I know. Multigenerational trips live or die on pace. Grandparents might need a nap. Toddlers definitely will. And the adults in the middle likely want a night out by themselves. You have to build all of that in, and it’s what should decide where you stay, not just how long you’re gone.

That’s where a resort fee can really earn its keep. In the places we work most, Hawaiʻi especially, that fee is often the difference between a plain condo and a kids club, a pool that occupies everyone for an afternoon, a few restaurant options, and someone else handling the snorkeling or SUP logistics so you don’t have to.

If you’re heading to Europe, just FYI, our guide to planning a family trip to Europe goes deeper on building trips around pace rather than the itinerary.

The Booking Window Is Now

Another part people underestimate… how far ahead this actually has to happen. Hawaiʻi spring break housing and Europe summer villas are booking right now. If a multigenerational trip is anywhere on your 2027 list, you don’t need the full itinerary figured out today. You need the lodging handled.

Once that’s done, everything else (the restaurants, the day trips, who’s doing what) can wait. For Hawaiʻi in particular, picking the right island makes a real difference for a mixed-age group, and it’s the first decision I’d make.

Five milestones. One family. That’s a lot to lock down! Wish me luck, and if you’re staring down your own version of this puzzle, get moving on the booking. You can figure out the dinner reservations later.