1. Saint Augustine, FL
If you’ve been dreaming of a trip that feels like a history lesson without the school vibes, and lets you chill on the beach with a cocktail after, St. Augustine might just be your new favorite family vacation spot. It’s the oldest city in the U.S., which makes it a cool Memorial Day destination, packed with pirate ships, alligator farms, and plenty of kid-approved adventures.
Where to Stay: Casa Monica Resort & Spa has historic vibes and is walkable to everything.
2. Austin, TX
When most people think of Austin, they picture live music, BBQ, and tech bros on scooters. And while yes, that’s part of the vibe. This city is also shockingly great for families. If you’re looking for a vacation that’s equal parts fun for the kids and relaxing (or at least not chaotic) for the adults, Austin totally delivers.
Completely unique to Austin is the Congress Avenue Bridge Bats. Watch 1.5 million bats fly out at sunset—an unforgettable sight for kids!
Where to stay: Hyatt Regency Austin – Right on Lady Bird Lake, walkable to downtown, and perfect if you want a “resort-light” experience
3. Boston, MA
The city escape that’s perfect for a patriotic weekend! Boston might be known for history nerds, Red Sox diehards, and college students with too much caffeine, but here’s the plot twist: it’s actually a dream destination for families. Think cobblestone streets with stroller access, hands-on museums that aren’t boring, and fresh seafood your kids will want to eat…maybe. I remember the shock when my 3 year old couldn’t get enough Clam Chowder in Boston. If you are traveling with younger ones, check out the Freedom Trail but make it mini. Walk a few key stops (like Paul Revere’s House and Faneuil Hall), grab a soft pretzel, and call it a win. The full trail is 2.5 miles, so mix it up with snacks and playground breaks. There are plenty!
Where to stay: Check out all the adorable and cozy Airbnbs in Back Bay or North End – Great neighborhoods that put you close to everything, with a more local vibe.
4. Lake Oconee, GA
Tucked between Atlanta and Augusta, this lakeside escape is where Southern charm meets low-key luxury. It’s part nature escape, part country club vibes and perfect for families looking to unplug (but still enjoy a good brunch and spa service). Visit neighboring Downtown Greensboro + Eatonton, two charming small towns with old-school ice cream shops, boutiques, and photo ops in front of colorful murals. Great for a morning wander and caffeine run.
Read all about our time at Lake Oconee on my previous blog.
Where to Stay: The Ritz-Carlton Reynolds. This is a splurge but very family-friendly with s’mores nights, a lakeside beach, free bikes, and a spa for you.
5. Big Cedar Lodge, MO
My kids still talk about this vacation spot so it’s always on my list of recommendations for families. Big Cedar Lodge commemorates Memorial Day with a series of events designed to honor the occasion and provide entertainment for the whole family like a patriotic picnic, a run to remember 5k, and a Paddleboat Family Fishing Tournament. Beyond the Memorial Day events, Big Cedar Lodge offers a plethora of activities to keep families engaged all weekend long.
Read more about Big Cedar Lodge, the luxury wilderness resort on my previous blog.
