When families ask me where they should go next, my first question usually isn’t, “Where have you been?”

It’s, “What does everyone actually enjoy doing on vacation?”

Are your kids happiest when there’s something new to explore? Do you want a few days when nobody needs to think about dinner? Are the grandparents joining you, or is this the year you introduce your family to Europe?

Those answers tell me much more than a list of popular destinations. For 2027, here’s where I’d start matching the trip to the people taking it.

If your family loves animals and outdoor adventures, I’d send you to Costa Rica.

‍For the family whose children stop to investigate every interesting creature, Costa Rica offers plenty to be curious about. Wildlife walks, chocolate experiences and outdoor adventures can give the trip a wonderful mix of discovery and fun.

I’d consider an Arenal-area stay paired with beach time if your vacation is long enough to enjoy both comfortably. An adventurous morning followed by an afternoon at the pool can be a much better balance than scheduling another excursion.

‍The planning detail that matters: Travel between regions takes a meaningful bite out of your vacation. I’d rather choose fewer places and give you time to enjoy them. Activities also need to fit everyone’s ages, comfort levels and abilities.

‍If your family loves Disney, but everyone wants a little independence, I’d suggest a Disney cruise.

‍Some families want the Disney experience and a vacation that gives everyone room to follow their own interests.

Disney Cruise Line offers family activities alongside age-specific programming and adult-exclusive spaces. That creates opportunities to spend time together and enjoy parts of the day separately. Offerings vary by ship.

I’d build the trip around a few shared moments: dinner, a show or a port experience everyone is excited about. The rest of the day can have some flexibility.

‍The planning detail that matters: I’d match the ship, sailing length and itinerary to your family before choosing a stateroom. Children’s ages and eligibility for youth programming matter, too. A short sailing may be a useful introduction, but it can feel brief if you’re hoping for several days to settle in.

If your family loves wildlife and big scenery, I’d send you to Alaska.

‍For families who would happily trade a beach afternoon for a chance to spot a whale, Alaska would be high on my list.

Glaciers, coastal scenery and wildlife experiences offer a different kind of family vacation. There’s plenty to talk about together, whether you explore by cruise, on land or through a combination of both.

I’d especially consider it for a multigenerational trip when the shared interest is discovery. Everyone can enjoy the same destination while choosing different levels of activity.

‍The planning detail that matters: “An Alaska cruise” isn’t one interchangeable experience. I’d compare the actual route, port time and glacier viewing opportunities, then leave room in the budget for the excursions that matter most. Wildlife sightings are always a possibility, never a promise.

‍If your family loves food and exploring, I’d send you to Italy, with fewer stops.

‍Italy would be one of my first considerations for a family that enjoys trying local foods, wandering through towns and discovering something together. Food can be a natural way into the destination, especially for children who connect more readily with pizza than a long museum visit.

I’d build the itinerary around a manageable number of bases, with experiences such as a cooking class, a guided introduction to a city or time in the countryside.

There should also be room for the little things: finding a favorite bakery, lingering over lunch or returning to the same gelato shop.

‍The planning detail that matters: Moving hotels repeatedly can wear out even enthusiastic travelers. Your family’s tolerance for walking, stairs, summer heat and transfers should shape the route just as much as the places on your wish list.

If your family loves pool days and fewer decisions, I’d start with a Caribbean all-inclusive.

‍If your ideal day includes breakfast together, a little beach or pool time and no debate about where to drive for dinner, I’d consider a family all-inclusive in the Caribbean.

The right resort can give the kids activities to look forward to while allowing the adults to slow down. But I’d choose the property around how your family will use it, rather than how impressive the amenities list looks.

‍The planning detail that matters: A beautiful beach photograph doesn’t tell us whether the water typically suits your swimmers, how far your room is from the pool or whether the children’s programming fits your kids. Room arrangements, beach conditions, dining and transfer time all belong in the decision.

Ronna Recommends

‍You may have recognized your family in more than one of these descriptions. That’s where the real planning begins.

Before choosing your 2027 destination, ask everyone:

•    What’s one thing you really want to do?

•    What made our last vacation feel tiring or frustrating?

•    How much activity would we enjoy in a typical day?

Those answers help me distinguish between a destination you’d love to see and a trip you’d love to take.

A family that enjoys adventure may still need quiet afternoons. Grandparents may want to join the big excursion, while the teenagers would prefer to sleep in. The goal is to make room for those differences.

Dreaming of your family’s 2027 match or beyond? I would love to help you design the perfect land or sea experience for your family!  Click here to schedule a “Let’s Get Acquainted Session” with me so we can start planning your family’s next great adventure.

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