6 Can’t-Miss Stops for Your Florida Keys Family Vacation

If you’ve been dreaming of a trip that brings the whole family together—toddlers to teens, grandparents to grown kids—there’s no better destination than the Florida Keys. With sunshine year-round, laid-back island charm, and more to see and do than you’ll find anywhere else on one beautiful stretch of road, the Keys are the perfect setting for a Florida Keys multigenerational vacation.

Not sure where to start? Here are six unforgettable experiences—one in each major stop along the Keys—that make planning your Florida Keys family vacation as fun as the trip itself.

Key Largo: Snorkeling at John Pennekamp Coral Reef State Park

Why You’ll Love It:

Key Largo is where the Florida Keys begin—and it sets the tone beautifully for a family vacation full of wonder. John Pennekamp Coral Reef State Park is America’s first underwater park and still one of the most spectacular places in the Keys to explore marine life together. The shallow reefs are accessible and calm, making them ideal for first-timers and little swimmers, while offering plenty of color and movement for more experienced snorkelers and divers. You’ll see schools of blue tang, brain coral, butterflyfish, and maybe even a sea turtle gliding by.

With glass-bottom boat tours, shaded picnic tables, and a small nature center, Pennekamp is more than just a snorkeling spot—it’s a full-family experience that invites both activity and ease. It’s one of those rare places where everyone can enjoy the same view, no matter how they choose to explore it.

Our Pick in Key Largo: Snorkeling or Diving to the Christ of the Abyss

One of the most iconic images in the Florida Keys, the Christ of the Abyss statue rests 25 feet below the surface at the Dry Rocks reef. This 9-foot bronze statue of Jesus stands with arms outstretched, surrounded by coral formations and swaying sea fans. Accessible by snorkel and dive tours from Pennekamp, it’s an awe-inspiring, almost spiritual sight—equal parts art, reef, and sacred stillness. Families say it’s the moment everyone remembers. A must-see for both divers and curious snorkelers, especially those looking for something truly unique and meaningful to share.

Islamorada: Feeding the Tarpon at Robbie’s Marina

Why You’ll Love It:

There’s a reason Robbie’s Marina is voted the #1 place to visit in Islamorada—its blend of local flavor, family fun, and accessible excitement. At the tarpon feeding, watching a massive silver tarpon leap out of the water to take bait from small hands never gets old. Children squeak; adults cheer; shared laughter echoes over the glistening water.

But Robbie’s is more than a fish‑feeding spectacle. It’s a destination in itself: open-air artisan markets, waterfront restaurants serving fresh seafood, local art stands, and shaded docks where everyone can linger. Whether you’re browsing souvenir shops or sipping ice-cold lemonade, there’s something for every tempo and temperament. It’s quirky yet comfortable—a laid-back afternoon any family will remember.

Our Pick in Islamorada: Kayak Tours with Robbie’s Kayak Shack

For hands-on adventure, these rainforest-like eco-tours are consistently praised as among the top Florida Keys things to do. Glide through mangrove tunnels toward Indian Key State Park, beach your kayak, explore island ruins, snorkel in turquoise shallows, and ride alongside fish beneath palm-fringed skies. Reviewers call it “one of our best kayaking experiences”—easy to manage and suitable for paddlers of different ability levels.

Grassy Key: Dolphin Research Center

Why You’ll Love It:

Dolphin Research Center isn’t just an animal show—it’s a place of connection, science, and heartfelt discovery. Programs include educational demonstrations, feeding, touching, and sometimes swimming with dolphins in shallow lagoon-style enclosures. Lectures on marine behavior and conservation are woven into every experience, so your kiddos learn while engaged and inspired.

Even for those who stay dry, watching dolphins play and seemingly respond to visitors is meaningful. The center’s intent—to build empathy alongside delight—resonates across every age group. It’s perfect for a family that values authenticity and shared joy.

Our Pick in Grassy Key: Cable Wakeboarding at The Lagoon

For families with teens (or adventurous grown-ups!) looking to add a splash of excitement, cable wakeboarding at The Lagoon is one of the most talked-about things to do in Grassy Key. Instead of using a boat, riders are pulled by an overhead cable system—smooth, controlled, and beginner-friendly. The staff is patient and upbeat, offering guidance that makes first-timers feel like pros in no time. There’s also kneeboarding and paddleboarding for different comfort levels, and plenty of room for cheering from shore.

Even those who aren’t riding love watching the action from shaded loungers or picnic tables nearby. It’s a high-energy, laugh-filled experience that brings out a little friendly competition and a whole lot of family bonding. And because it’s tucked in a scenic, uncrowded part of the island, it still feels calm, safe, and refreshingly local.

Marathon: Visiting the Turtle Hospital

Why You’ll Love It:

Marathon sits right in the heart of the Keys, making it a favorite home base for family travelers—and one of its most meaningful experiences is the Turtle Hospital. This working hospital rescues, rehabilitates, and releases injured sea turtles, and offers guided tours where guests can meet the turtles up close and learn their individual stories.

From toddlers asking curious questions to teens snapping selfies with “Bubble Butt,” it’s a place that educates and connects without ever feeling like a classroom. You’ll leave inspired—not just by the incredible animals, but by the people dedicating their lives to helping them heal. It’s a feel-good stop that’s both grounding and memorable.

Our Pick in Marathon: Spending the Day at Sombrero Beach

For pure ease and island beauty, Sombrero Beach is a top-tier pick for families looking to relax without the chaos of crowds. It’s one of the best-kept secrets in the Florida Keys—free to access, well-maintained, and wonderfully uncrowded. With soft white sand, swaying palms, shaded picnic areas, and a gentle slope into turquoise water, it’s perfect for all ages. There’s a playground for the little ones, space to throw a frisbee or set up chairs, and clean restrooms on-site. It’s wheelchair accessible and dog-friendly too, making it inclusive for the entire crew. Whether you’re building sandcastles, reading under the palms, or just listening to the waves roll in, this is the kind of beach day that fills the family photo album.

Big Pine Key: National Key Deer Refuge

Why You’ll Love It:

This peaceful refuge is a standout among Florida Keys things to do—especially for multigenerational trips. These pint-sized, endangered deer are found nowhere else on Earth, making every sighting feel like something truly special. About the size of a golden retriever, they roam freely and are surprisingly gentle and unafraid, often wandering close enough for a quiet, heartwarming encounter. Spotting one feels serendipitous, as though you’ve entered a storybook. Once on the brink of extinction, they’ve made a slow and inspiring comeback thanks to decades of conservation efforts at the National Key Deer Refuge. Spotting one—especially with kids or grandkids by your side—isn’t just cute; it’s meaningful. It sparks conversations about protecting wildlife and offers a rare kind of quiet connection to nature.

Our Pick in Big Pine Key: Lunch at No Name Pub

Tucked down a quiet side road with a name that’s both literal and legendary, No Name Pub is one of the most beloved hidden gems in the Keys. Originally opened in the 1930s as a general store, it’s now a funky, welcoming eatery plastered with thousands of signed dollar bills from guests around the world.

The food is delicious—crispy fish fingers, fresh pizza, cold beer, and Key lime pie that gets rave reviews—and the vibe is pure island charm. It’s casual, cool, and perfect for a mid-day pause after spotting deer in the refuge. Kids will love the quirky atmosphere (and hunting for the funniest dollar bill on the wall), while adults can soak in the laid-back feel of a Keys institution that feels like part restaurant, part time capsule. It’s exactly the kind of spot that becomes part of your vacation story.

Key West: Ride the Conch Tour Train

Why You’ll Love It:

Key West is the final stop along the Overseas Highway, and the Conch Tour Train is hands-down the best way to take it all in—without exhausting the crew. This open-air trolley rolls gently through the island’s colorful streets while a guide shares stories of pirates, poets, presidents, and everything in between.

It’s a wonderful introduction to the area, especially for first-time visitors or families with a wide range of energy levels. You can hop on and off at historic spots like the Ernest Hemingway Home, the Key West Lighthouse, or the quirky shops along Duval Street. Whether you ride it start to finish or use it to navigate the day, it gives everyone a sense of place—without the need to coordinate parking or navigate unfamiliar streets on foot.

Our Pick in Key West: The Daily Sunset Celebration at Mallory Square

Every evening, as the sun begins to sink over the Gulf of Mexico, Key West comes together in a celebration unlike any other. The Sunset Celebration at Mallory Square is part street fair, part magic show, and part island tradition—and it’s absolutely one of the most unforgettable Florida Keys family vacation moments.

Street performers juggle fire, play live music, or wow the crowd with offbeat comedy acts. Artisans sell handmade crafts. Food vendors offer local favorites, from conch fritters to fresh-squeezed lemonade. And as the sky turns from gold to coral to indigo, you’ll be standing with your toes on the seawall, watching the sun melt into the horizon while sailboats drift past.

It’s vibrant, soulful, and perfect for all ages. Teens take selfies, kids dance to the music, grandparents relax with a cool drink in hand—and no one’s checking the time. This is the Keys at their most joyful. It’s not just something to see—it’s something to feel.

End Each Day at Casa Feliz

After full days of discovery, return to Casa Feliz—an oasis crafted for multigenerational families. With amenities like a private beach, pool, pizza oven nights, movie marathons, fire‑table s’mores, paddleboards, and full kitchen set-up, the house feels both luxurious and homey. The little extras—from shampoo to games—mean zero planning on your part. It’s the perfect backdrop for the laughter, quiet moments, and legacy-in-the-making that define a successful family vacation.

Escape the ordinary and book your stay direct for the best rates at: www.casafelizfloridakeys.com.