How to Spend 3–5 Days Driving the Overseas Highway with Kids: Must-See Stops Between Key Largo and Key West

The Overseas Highway (U.S. 1) is one of America’s most iconic scenic drives. Stretching 113 miles across 42 bridges from Key Largo to Key West, it offers turquoise water views, historic sites, and plenty of family-friendly attractions. If you’re traveling with kids, this road trip can be as adventurous or as relaxing as you’d like. With the right planning, a Florida Keys itinerary can combine snorkeling, wildlife encounters, and fun pit stops that keep both parents and children happy.

Day 1: Start in Key Largo – The Dive Capital of the World

Must-See Stops in Key Largo:

• John Pennekamp Coral Reef State Park – The first underwater state park in the U.S., perfect for glass-bottom boat tours, kayaking, or snorkeling. Kid-friendly rentals available.
• Florida Keys Wild Bird Rehabilitation Center – Free admission, donations encouraged. Children can see rescued pelicans, owls, and other coastal birds up close.
• Key Largo Chocolates – A fun treat stop for ice cream and handmade sweets after a day of exploring.

Pro Tip: Spend your first night in Key Largo to break up the trip and enjoy sunset views at a waterfront restaurant.

Day 2: Islamorada – Family Adventures on the Water

Known as the “Sportfishing Capital of the World,” Islamorada is also packed with kid-friendly attractions.

Best Stops in Islamorada with Kids:

• Robbie’s Marina – A Florida Keys classic. Feed the giant tarpon, browse open-air shops, and grab fresh seafood.
• Theater of the Sea – A marine park where kids can interact with dolphins, sea lions, and stingrays.
• Windley Key Fossil Reef Geological State Park – Great for a short family hike with educational signage about ancient coral formations.

Overnight Tip: Stay at a family-friendly resort like Postcard Inn, Cheeca Lodge or rent a vacation home with pool access.

Day 3: Marathon – The Heart of the Keys

Halfway down the highway lies Marathon, a great base for families.

Must-See Marathon Stops:

• Florida Keys Aquarium Encounters – Hands-on marine life exhibits where kids can touch stingrays, starfish, and even feed sharks.
• Sombrero Beach – One of the best sandy beaches in the Keys, with picnic areas, playgrounds, and calm waters.
• Seven Mile Bridge – Drive across one of the longest bridges in the world, with panoramic water views.

Optional Extra Day: Spend a second night here if you want a slower pace and time for a snorkeling trip or kayaking through mangroves.

Day 4: Big Pine Key & The Lower Keys – Nature Encounters

This area is quieter and less commercial, making it perfect for a family nature day. If you’re on the search for Key Deer, make sure to check out famous No Name Pub for pizza and apps!

Kid-Friendly Stops in the Lower Keys:

• National Key Deer Refuge – Spot endangered Key deer (they’re tiny and child-sized, making them especially fun for kids to see).
• Bahia Honda State Park – Known for its shallow, calm beaches and nature trails—ideal for young children to swim and explore.
• Blue Hole – A freshwater pond on Big Pine Key with turtles, fish, and occasional alligators.

Day 5: Key West – The Final Destination

Finish your road trip in vibrant Key West.

Family Activities in Key West:

• Key West Butterfly & Nature Conservatory – Walk through a glass-enclosed habitat filled with butterflies, exotic birds, and tropical plants.
• Fort Zachary Taylor Historic State Park – A mix of history and beach fun; kids can explore the fort and swim at the sandy shoreline.
• Mallory Square Sunset Celebration – Street performers, local artisans, and food vendors create a festive atmosphere for the whole family.

Bonus: If you have teens, consider a visit to the Shipwreck Treasure Museum or a guided snorkeling trip to Dry Tortugas National Park. Key West is also known for the best Haunted Ghost Tours! Find Robert the Doll on a guided bus tour.

Sample 3–5 Day Overseas Highway Itinerary for Families

3 Days:

• Day 1: Key Largo → Islamorada
• Day 2: Marathon → Seven Mile Bridge
• Day 3: Big Pine Key → Key West

5 Days:

• Day 1: Key Largo overnight
• Day 2: Islamorada overnight
• Day 3: Marathon overnight
• Day 4: Big Pine Key overnight
• Day 5: Key West (2–3 nights if extending your stay)

Travel Tips for Families Driving the Overseas Highway

• Pack snacks & water: Some stretches have limited stops.
• Break up the drive: There are so many unique stops and hidden beaches along the highway.
• Bring snorkel gear & water shoes: Many roadside parks have shallow beaches perfect for a quick dip.
• Travel off-peak: Weekdays or early mornings avoid the heaviest traffic.
• Check seasonal events: From Mini Lobster Season in July to holiday festivals in December, family-friendly events add fun along the way and a chance to meet so many locals!

Making Family Memories on the Overseas Highway

A 3–5 day Florida Keys road trip down the Overseas Highway is more than just a drive — it’s a once-in-a-lifetime family adventure. From snorkeling coral reefs in Key Largo to spotting Key deer in Big Pine Key and watching the sunset in Key West, every stop has something special for kids and parents alike. With smart planning, you’ll create a trip filled with memories, laughter, and endless photo opportunities.