Multigenerational Trips

If ever there was a time to engage a Travel Advisor to help families sort through their options, simplify the logistics and bookings, and plan the vacation of everyone’s dreams, this is it. We’ve helped all types of families seeking any number of travel experiences. From a yearly reunion at a beach resort and a wedding in Greece to bucket-list trips like an Alaskan cruise and an African safari, we’ve planned it all — and for any number of family members. Not only can we secure great perks for our clients, but we can handle the fussy details like ground transportation and group dining reservations.

Our favorite destinations for multigenerational trips include:

Ireland

Learning more about ancestors often precipitates the planning of a trip to Ireland, but visitors soon discover that this destination appeals to families for many reasons, like beautiful hikes through green fields, farm visits, castle tours and more. Multigenerational groups have enjoyed all kinds of accommodations, from renting out an entire manor house to staying at a full-service resort with lots of activities onsite. Regardless of where you stay or which regions you visit, you’ll love the legendary Irish hospitality.

Cruise

Many multigenerational groups gravitate toward cruises because of the streamlined logistics. There’s no changing accommodations, lots to do on board and enough variety to please everyone. Cruise experiences aren’t limited to big ships island-hopping in the Caribbean, though. Families have enjoyed traveling around Europe this way, including on the Mediterranean, the Baltic and smaller rivers that run throughout the continent. We can help plan intimate excursions away from the crowds on the ship to make the trip truly special and customized.

Italy

Year after year, Italy remains our most popular destination to send families. Multigenerational or multi-family groups love it for immersive cultural experiences like cooking classes and museum tours, plus kid-friendly accommodation options full of wide-open spaces for play and pools to splash in on hot summer afternoons. Because we know so many vendors here personally, our activity options go beyond families’ wildest dreams, like watching the famous Palio horse race in Siena from a private apartment balcony.

Costa Rica

Its location near the equator means Costa Rica works as a destination throughout the four seasons, especially for those families who prioritize warm weather. There’s also a lot of flexibility here: Adventurous families love doing physical activities like ziplining or whitewater rafting, but these can be paired with relaxing days by the beach or pool. Animal encounters, like laughing at howler monkeys in the jungle or spotting sloths high in the trees, are an ideal bonding opportunity that works across the generations.

Alaska

Most people want to see Alaska at some point in their lives, so why not go together and experience it through everyone’s eyes — children through grandparents? Large and small ships can customize excursions to meet age and physical limitations.

Dude Ranch

These trips work really well for families who want to reconnect during a week of summer fun in a place of natural beauty with lots to do. When choosing which ranch meets the needs of your multigenerational group, decide what type of lodging works best, whether it be standalone homes big enough for the whole group or private cabins for each individual family. A robust schedule of off-trail activities is also ideal for those who won’t be riding each day.

Hawaii

There’s something so universally appealing about Hawaii that it’s easy to convince everyone from toddlers to teens to grandparents to get on board. Leisurely relaxation on the beach or around a family-friendly resort pairs perfectly with cultural experiences like pineapple farm tours, a visit to Pearl Harbor or a luau dinner.

Dominican Republic

If traveling all the way to Hawaii as a multigenerational group seems too much of a hassle when all you really want is to relax together in a tropical paradise, consider the Dominican Republic instead. Not only are there quick, direct flights from many U.S. locations, but it’s really easy to get around this island and explore its various ecosystems.

Don’t get overwhelmed by your aunt’s food allergies, your cousin’s aversion to cold weather or your grandma’s recent knee replacement. And certainly don’t let the mind-boggling logistics of group travel stop you from seeing the world with the entire family. Let us put our global connections and travel know-how to work for your family. We’ll handle the intricate details and help craft a multigenerational trip that will be enjoyable for all.