Oh, I am so excited to tell you about one of my absolute favorite ways to recharge! There is something truly magical about the way the air changes as you drive south into Florida. You know that moment when you roll the windows down, the salt air hits your face, and suddenly the “to-do” lists and the busy school schedules just seem to melt away? That’s the feeling of the tropics, and you don’t even need a passport to find it.
As a mom who is always on the go, I’ve learned that the secret to a successful family getaway is finding that perfect balance between adventure and pure, unadulterated relaxation. My family and I have spent so much time exploring the Florida coastline, and I’ve carefully planned this journey to share the hidden gems we’ve discovered. From the laid-back “Old Florida” charm of the Keys to the sophisticated luxury of the Gold Coast, this trip is all about creating lasting memories by the water.
Whether you’re looking to immerse yourself in the vibrant culture of Key West or find a quiet stretch of white sand in Naples, I’ve got some wonderful recommendations for you. We’re going to look at some incredible spots where the rooms are spacious enough for the whole crew, the food is delightful, and the experiences are unlike anything else. So, grab a cool drink, and let’s dive into your next sunshine-filled escape!
The Heart of Islamorada: La Siesta Resort Villas
Our journey begins in the “Sport Fishing Capital of the World,” Islamorada. If you haven’t been, it is such a unique destination. It feels a bit like stepping into a postcard from a simpler time. When we visit, we love staying at La Siesta Resort Villas. This place is a dream for families who want a little more room to breathe.
Instead of a cramped hotel room, you can tuck the kids into a multi-bedroom villa or a cozy cottage. Having a kitchen and a living area makes such a difference—it’s so nice to be able to whip up a quick breakfast or have a quiet place for the adults to chat after the kids fall asleep. The style here is very “island chic”—think bright whites, turquoise accents, and plenty of natural light.
What to do in Islamorada:
- Feed the Tarpon at Robbie’s of Islamorada: You absolutely must do this! It’s a local rite of passage. You buy a bucket of bait and watch these massive “Silver Kings” jump right out of the water to grab a snack. My kids were terrified and thrilled all at once—it makes for the best photos!
- The Florida Keys Wild Bird Rehabilitation Center: This is such a thoughtful experience. It’s a peaceful boardwalk where you can see rescued owls, pelicans, and hawks. It’s a great way to expose the kids to conservation efforts in a beautiful setting.
- Snorkeling at Hen and Chickens Reef: The water here is so clear and shallow, which is perfect for younger swimmers. You’ll see vibrant purple sea fans and maybe even a friendly sea turtle!
After a day of exploring, we love coming back to the resort’s private beach. There’s something so therapeutic about sitting in a hammock under a palm tree while the kids play in the sand nearby. It’s the ultimate way to settle into “island time.”
Key West Charm at Southernmost Beach Resort
As you continue down the Overseas Highway—which, by the way, is one of the most beautiful drives in the world—you’ll eventually hit the end of the road: Key West. Now, Key West can be high-energy, but I think the best way to experience it is from the quiet, sophisticated end of Duval Street.
Southernmost Beach Resort is where we always choose to stay. It spans six beachfront acres, and even though it’s close to the action, it feels like a private sanctuary. The resort has this wonderful, classic Key West architecture with wraparound porches and lush tropical gardens. It’s incredibly charming and feels so authentic to the island’s history.
Authentic Key West Experiences:
- The Hemingway Home and Museum: Even if your kids aren’t big readers yet, they will love the “polydactyl” (six-toed) cats that roam the grounds. The history is fascinating, and the architecture is stunning.
- Sunset Celebration at Mallory Square: It’s a bit of a tourist staple, but for good reason! The street performers, the local crafts, and that big orange sun sinking into the Gulf of Mexico… it’s a shared experience you’ll never forget.
- Key West Butterfly & Nature Conservatory: Walk through a glass-enclosed habitat with hundreds of butterflies fluttering around you. It is such a serene and magical experience for all ages.
At the resort, make sure to grab a table at the Southernmost Beach Café. There is nothing like eating fresh Mahi-Mahi tacos with your toes literally in the sand. And don’t forget a slice of Key Lime Pie—it’s mandatory when you’re this far south!
Fort Lauderdale Elegance: Pelican Grand Beach Resort
Leaving the Keys is always bittersweet, but the excitement of the Gold Coast awaits! As we head north toward Fort Lauderdale, the vibe shifts from “island rustic” to “oceanfront luxury.” If you want to experience the grandeur of the Florida coast, Pelican Grand Beach Resort is the place to be.
What I love about this property is that it sits right on the Atlantic Ocean. In a city where many hotels are across the street from the beach, being able to walk directly onto the sand is a total game-changer. The resort has a very elegant, Old Florida feel with its massive rocking chair porch—it’s the perfect spot for a morning coffee or an evening cocktail.
Family Fun in Fort Lauderdale:
- The Lazy River: This is a huge hit! The resort has its own Lazy River where you can just grab a tube and float the afternoon away. It’s so relaxing, and I may have spent more time in it than the kids did!
- Fort Lauderdale Water Taxi Tours: Fort Lauderdale is known as the “Venice of America” because of its intricate canal system. Taking the water taxi is a fantastic way to see the incredible mansions and yachts while getting a bit of local history.
- PURE Spa: Moms, you have to treat yourself here. The spa is on the 11th floor and has floor-to-ceiling windows overlooking the ocean. I had a treatment there last year, and watching the waves while getting a massage was pure bliss.
For dinner, OCEAN2000 is the resort’s signature restaurant. The seafood is incredibly fresh, and the views of the moon reflecting off the Atlantic are just spectacular. It’s the kind of meal where you find yourself lingering just to soak in the atmosphere.
Sophisticated Sunsets at Sole Miami
Continuing just a little further south into Sunny Isles Beach (right between Fort Lauderdale and Miami), you’ll find Sole Miami. This resort has a much more contemporary, boutique feel. It’s sleek, modern, and offers some of the most incredible views of the skyline and the ocean.
One of the highlights here is the “Sole on the Ocean” experience. The rooms are designed with floor-to-ceiling windows, so you feel completely immersed in the blue of the water and the sky. It’s a very stylish place, but still feels very welcoming to families who appreciate good design and great service.
Exploring the Area:
- Oleta River State Park: Just a short drive away, you can rent kayaks and paddle through mangrove trails. It feels like a world away from the high-rises and is such a great way to see the natural side of Florida.
- BaleenKitchen: This is the resort’s main restaurant, and the food is fantastic. They do a wonderful job of blending local flavors with international flair. Try to snag a table on the terrace at sunset—the colors in the sky are just incredible.
- High-End Shopping: If you’re in the mood for a little retail therapy, the Aventura Mall is nearby. It’s one of the best shopping destinations in the country, and it even has some amazing art installations that the kids will find cool.
Sole Miami feels like a little slice of the Mediterranean right here in Florida. It’s sophisticated, but the staff is so friendly and helpful that you’ll feel right at home the moment you walk through the door.
Gulf Coast Serenity: Laplaya Beach Golf Resort
To round out our Florida tour, we have to head over to the west coast. The Gulf side of Florida is known for its calm, turquoise waters and those powdery white sand beaches that feel like sugar between your toes. In Naples, the crown jewel is definitely Laplaya Beach Golf Resort.
This resort is the epitome of relaxed luxury. It’s tucked away in a more residential area, so it feels very private and exclusive. The style is classic Florida—think lush palms, crisp white linens, and wide-open spaces. If your family loves the beach but also enjoys a bit of golf or a world-class spa, this is your destination.
Naples Highlights:
- Shelling on the Beach: The Gulf is famous for its shells! We spent hours walking the tide line looking for “treasures.” It’s such a simple, grounding activity that really lets you connect with nature.
- The Naples Pier: A walk out onto the pier is a must. It’s a great spot for people-watching, and you’ll almost always spot dolphins playing in the surf.
- Audubon’s Corkscrew Swamp Sanctuary: For a truly unique inland experience, head to this boardwalk that winds through an ancient cypress forest. It’s peaceful, shady, and you’ll see all kinds of Florida wildlife, from alligators to rare birds.
At LaPlaya, you have to spend time at the Tiki Bar. It’s the perfect place for a casual lunch by the pool. And for a special final dinner, BALEEN Naples offers “toes in the sand” dining where you can watch the sunset while enjoying some of the best seafood in the state. It’s the perfect way to toast to a wonderful journey and all the memories you’ve made.
Creating Memories that Last
You know, at the end of the day, travel isn’t just about the places we go—it’s about the people we’re with and the stories we bring home. Whether it was the laugh-out-loud moment of feeding tarpon in Islamorada or the quiet peace of watching a Gulf sunset in Naples, these are the experiences that stick with us.
I truly hope this guide helps you plan a thoughtful and incredible escape for your family. Florida has so much to offer, and choosing the right home base makes all the difference. These Curator properties are more than just places to sleep; they are destinations in themselves that offer comfort, style, and a real connection to the local culture.
So, are you ready to start packing? I promise, once you get a taste of the tropics, you’ll be dreaming of your next Florida journey before you even get home!
