Memorial Day is the unofficial start of summer — and the best family destinations fill up weeks in advance. Here are the five trips I'm booking most right now.
Memorial Day weekend is the unofficial start of summer — and the best family destinations fill up weeks in advance. If you haven't locked in your plans yet, here are the five trips I'm recommending most to families right now. All of these still have availability, but not for long.
San Juan is one of the hottest family destinations of 2026, with bookings up over 50% year-over-year. And it's easy to see why: no passport required for US citizens, direct flights from most major cities in under 4 hours, and a mix of beautiful beaches, Old San Juan's colorful streets, and family-friendly resorts. El Conquistador and the Condado Vanderbilt are both excellent options for families who want a resort experience with easy access to the city.
**Best for:** Families who want Caribbean vibes without international travel hassle.
If you want the gold standard in family all-inclusive, Beaches Turks & Caicos is it. Sesame Street characters roaming the resort, a massive waterpark, multiple pools, a kids' club for every age group, and Grace Bay — one of the most beautiful beaches in the world. Suites and premium rooms sell out 3–4 months in advance, so if you're thinking about summer, reach out today.
**Best for:** Families who want everything taken care of — food, entertainment, and activities all included.
Orlando is the most searched domestic destination for summer 2026, and for good reason: **Universal's Epic Universe** opens this summer, adding a fifth theme park to the lineup. This is the year to go. Between Disney World, Universal, and now Epic Universe, you could spend two weeks in Orlando and still not see everything. I help families plan Orlando trips that maximize their time and budget — no wasted days, no meltdowns from over-scheduling.
**Best for:** Families with kids of any age who love theme parks.
A 4–7 night Caribbean cruise departing from Miami, Port Canaveral, or Galveston is one of the best values in family travel, full stop. Kids' programming, multiple dining options, a waterpark on the ship, and island stops — all included in one price. Royal Caribbean and Carnival both have excellent family sailings this summer. Prices are still reasonable if you book in the next few weeks, but inside and oceanview cabins are going fast.
**Best for:** Families who want variety — multiple destinations, activities, and dining options in one trip.
For families who want a beach house experience without the all-inclusive price tag, the Outer Banks delivers. Rent a house, bring the grandparents, and let the kids run free on some of the most beautiful and uncrowded beaches on the East Coast. OBX is one of my favorite recommendations for multigenerational families — there's room for everyone, the pace is relaxed, and the memories are real.
**Best for:** Multigenerational families, families on a budget, or anyone who wants a low-key beach week.
Memorial Day weekend is less than three weeks away, and summer availability is shrinking fast. If any of these destinations speak to your family, reach out today and let's figure out what's still available. I'll do the research, compare the options, and present you with the best choices — so you don't have to spend hours on Google.
Ready to plan your Memorial Day or summer trip? [Let's talk.](#contact)