fbpx

Don’t Book Family Trips, Build Legacies Instead.

[additional-authors]
July 9, 2026

Why cruises, safaris, and road trips are the three greatest ways to travel as a family in 2026, and how to do all of them right.

Some trips are just vacations. And then there are the ones your family never stops talking about. The road trip where you got a little lost and found something amazing, the safari morning when everyone fell silent watching a pride of lions (with cubs) walk by the swimming pool deck, or the time the ellies came to drink from the pool where you were relaxing… the holiday cruise where nobody had to cook and everyone actually relaxed and focused on each other. This is a guide to book those trips. The ones worth planning, and planning well.

Summer is here. And if you are anything like many of the families I talk to, you have been meaning to plan something extraordinary for months. Something beyond the usual resort week. Something everyone will actually remember but then somehow June arrived before the itinerary did. I get it. Life is relentless. But… some of the best trips I have ever taken, personally and professionally, came together in weeks, not months. So let’s talk about what is still possible, what is worth doing properly, and why 2026 might genuinely be the best year in recent memory to travel as a family, in all its gloriously chaotic, multigenerational, nobody-agrees-on-the-restaurant reality.

My personal experience: The two RV camper road trips through Southern Africa with the entire “fandamily” all talking at once. The safari where my seven-year-old niece fell silent watching a lion with her cubs walking next to the vehicle. The river cruise where my grandmother cried at the Christmas markets because it looked exactly like the village she grew up in.

These are not accidents, they are what happens when you choose the right format for the right family. And in my experience, here are the trips that work: the White Lotus trip, the Road Trip, the Cruise, and the Safari. 

The White Lotus Effect: Go Where the Story Takes You

I will start with the trip that has been living rent-free in everyone’s head since Season 3. If your group chat has not exploded about Thailand or any of those destinations yet, give it a week. White Lotus did what great storytelling has always done. It made a destination feel urgent, cinematic, and deeply personal all at once. The difference in 2026 is the speed at which that desire travels. Within weeks of the season airing, searches for Koh Samui spiked, river cruise itineraries through Southeast Asia sold out, and families who had never once discussed Thailand were suddenly sending each other reels about infinity pools overlooking the Gulf.

What makes this moment genuinely interesting for multigenerational travel is that for once, everyone is watching the same thing. The 26-year-old and the 66-year-old are both obsessed with the same show, dreaming about the same aesthetic and arguing about whether the villa is worth it. That shared cultural starting point is rarer than you think, and it is one of the most powerful catalysts for a multigenerational trip I have ever encountered. When the whole family already agrees on the vibe, half your planning battle is won before anyone opens a browser.

Road Trips: Start Close to Home.

After years of traveling all over the world, I’ve landed on four types of trips that I believe are genuinely the best formats for family travel, especially a multigenerational family. Road trips. Cruises. Safaris and Heritage trips. Each one works for a completely different reason and they cover almost every kind of family.

What makes road trips the ultimate multigenerational format is flexibility. Grandparents can sleep in while the younger ones hike at dawn. You can stop at the roadside market nobody planned for and you can take the scenic route just because someone spotted something interesting from the window. There are no excursions to cancel and no schedule to miss. The destinations are endless! Iceland’s Ring Road, the Scottish Highlands, a Patagonia circuit, a classic American National Parks run, or simply a long weekend to the mountains, a few hours from home. The journey is also the destination when you are on a road trip.

My family and I loved road trips, especially self drive safaris across Southern Africa, and winding drives through Europe, with the family (all ages) piled into vehicles together. We often camped and stopped when some gorgeous location caught our eye… and the best moments were seldom the ones on the itinerary and that is the best thing about road trips. To this day, one of my favorite things is to simply get in the car and drive. No fixed plan or any reservations. Just stop wherever I find an interesting spot along the way. During the pandemic, when the world effectively shut down, those spontaneous road trips kept me sane. Just the open road and the freedom to figure it out as I drove. Turns out you don’t need a passport to have an adventure and some of the most extraordinary trips start just a few hours from your front door.

Big Bear, California. Your SoCal Family Escape.

If you live in Southern California and haven’t done a Big Bear family trip yet, put it on the bucket list. It’s about two hours from Los Angeles and it works in every season. Big Bear has that rare quality of feeling like a real escape without requiring four connecting flights. It is one of those trips families do once and then find themselves going back three four times a year. It becomes a tradition before you even realize it.

In winter, Snow Summit and Bear Mountain offer skiing and snowboarding for all skill levels, and if your little ones have never seen snow before, watching their faces when it clicks is something you won’t forget. Summer opens up the lake for kayaking, paddleboarding, and long lazy afternoons on the water. Fall is golden with some of the best hiking and biking in Southern California. Spring brings wildflowers and fresh mountain air with far fewer crowds.

What makes Big Bear work so well for families is that there’s genuinely something for every age and every energy level. Grandparents can sit on a cabin deck with coffee or glass of wine and a enjoy a stunning view, while the kids tackle the slopes or the trails. Teens stay engaged, toddlers are enchanted by everything and you can choose from so many lodges and activities! You have the option of a cozy budget-friendly cabin tucked in the pines, or a fully appointed lodge with a hot tub, mountain views, and everything taken care of. Ultra luxe or totally down to earth, your choice.

Need last minute plans for a weekend away? Off to Big Bear! Need a romantic spot for a weekend away from the kids? Big Bear of course! Need a glow-up retreat for you and your besties before the wedding? Yep, you guessed it, Big Bear! Tap here for everything you need to know about planning a trip to Big Bear.

For Families Ready to Venture Further.

Beyond Big Bear, some of the most memorable family road trips takes shape with intention, where every stop builds on the last. Iceland’s Ring Road. The American National Parks circuit, by train! The Scottish Highlands. Patagonia. These aren’t trips you wing, they’re trips you build carefully, with the right properties pre-booked, buffer days planned in, and a few unexpected moments along the way that become the highlights of the whole journey.

✈   PRO TIP(s)

  • Always build in at least one buffer day per week of long distance road trips. Things run long, kids need downtime, and the best moments often happen when you’re not rushing to the next thing.

  • As your travel advisor I will add a small welcome touch at your first stop, a local treat, something personal waiting in the room that will set a warm tone that carries through the whole trip.

  • Working with a travel advisor makes a bigger difference on especially international road trips than almost any other style of travel. You can Google a route, but you can’t Google which properties are genuinely great for families (vs. which ones just say they are), which ferries are not operating any longer even though your AI search says it does or which roads get congested and when, or who to call when something doesn’t go to plan. That knowledge and those relationships are what turn a good trip into one your family talks about for years.

Cruising: One Bag, One Check-In, No-One Cooking Or Decorating = The Best Trip Ever.

Did you enjoy this article?
You'll love our roundtable.

Editor's Picks

Latest Articles

A Ka’ak By Any Other Name

A symbol of hospitality, families bake batches for holidays, family celebrations and visits with friends and relatives.

The Story That Never Goes Away

Rachel Goldberg-Polin, mother of slain hostage Hersh Goldberg-Polin, can’t stop speaking about her pain and the public love her body cannot always receive. She talks to the Journal about her son’s legacy and her new book.

Rosner’s Domain | A Dime-Store Abe: The Karhi Crisis

This week’s “Constitutional Crisis” is typical of the way the government operates. It issues a statement, or a tweet and then walks it back. Oops, we did not mean it. Or rather, we did, but we also meant to deny that we did.

Why Can’t We Be Friends?

If we want to see a less polarized society, both internally and beyond, we must emphatically reject the idea that political alignment is the predominant commonality for friendship.

Ruth-less, the Enigma of a Name

Jews spoke in two voices about Ruth, a kind of national schizophrenia, one with joyous chanting on Shavuos as the Book of Ruth was read; the other, removing her name from the chain-link of repeated names throughout the generations.

Honoring My Father: Saying Kaddish with Men

Saying kaddish every day tested my faith and commitment. It made me realize that there is no room for excuses. It taught me how to show up. It taught me that my voice can be heard, even when not expected.

More news and opinions than at a Shabbat dinner, right in your inbox.