Florida Keys Road Trip: Big Pine Key to Key Largo and Beyond

Robbie’s, a kitschy marina packed with photo ops and souvenirs in Islamorada.Robbie’s, a kitschy marina packed with photo ops and souvenirs in Islamorada.

If you’re headed to the Florida Keys, you’re probably doing Key West. And you should — it’s amazing.

But the family road trip isn’t over when you reach the southernmost point of the Continental U.S. As you head north to return home, the rest of the Florida Keys are calling, and you might even add on some sightseeing in Miami.

In this itinerary, I’ll cover where to stay and what to see as you drive up the A1A on a Florida Keys road trip from Big Pine Key to Key Largo (and beyond!). Allow a few days for a leisurely pace. You’re on island time after all.

Big Pine Key: Wildlife Spotting


Key deer grazing by the road in Big Pine Key, Florida

Key deer grazing by the road in Big Pine Key, Florida


The big thing to see here is the adorable and tiny key deer at the National Key Deer Refuge. They’re easy to spot. We drove down Key Deer Boulevard and saw several hanging out on the side of the road, munching on the grass.

If you do see deer, be sure to give them space as you snap photos. You can spot even more wildlife, like ospreys, marsh rabbits and turtles, if you take one of the trails and keep your eyes peeled.

Travel tip: There’s a shopping plaza conveniently at the intersection of Key Deer Boulevard and the A1A if you’re hungry. We picked up supplies (including a local lobster spread) from Winn-Dixie for an impromptu picnic.

Marathon: Staying at the Fairfield Inn and Suites

View in Florida Keys

View of paradise from our balcony.

Marathon is the perfect halfway point of the Florida Keys, so this is where you should stay. We loved the Fairfield Inn & Suites Marathon. We could use our Marriott points and enjoy a lavish continental breakfast spread, but it also had the indulgent feel of an island resort. From the sky blue walls to waterfront views to hammocks under a chickee hut, it’s full-on Florida Keys vibes.

A thoroughly modern room at the Fairfield Inn & Suites in Marathon, Florida

A thoroughly modern room at the Fairfield Inn & Suites in Marathon, Florida

Rooms at the Fairfield Inn & Suites in Marathon are clean and updated, equipped with WiFi and kitchenettes. For your vacationing pleasure, there’s an on-site tiki bar, two pools, a fitness center and a marina, where you can rent kayaks, paddleboards and jet skis.

I especially loved how close we were to everything! We visited Bahia Honda Key to the south twice since it took us only 20 minutes to get there. Islamorada is less than 30 minutes north. Even Key West is only about an hour away.

Marathon also has great beaches. Here are some other kid-friendly attractions in town.

  • Meet the sea turtles being rehabilitated at the Turtle Hospital. Be sure to sign up in advance for a guided tour.
  • Visit Aquarium Encounters, a marine park designed especially for kids, where you can interact with a shark, snorkel and more.
  • Wander the trails at Crane Point Hammock. You can spot birds, visit the museum and get a fish pedicure.

Islamorada: Roadside Attractions

Opened in 1946, Theater of the Sea is part of that pre-Disney Florida when so many tourist attractions blossomed along state highways. It’s a theater because the main draw is watching shows — by dolphins, sea lions, crocodiles, parrots and more. While it’s on the pricier side, Theater of the Sea is consistently one of the top-rated things to do north of Key West.

For more traditional roadside fun, hit up Robbie’s, a kitschy marina packed with photo ops and souvenirs. You eat at the restaurant and also feed the tarpons (for a fee).

Betsy, the world's largest lobster sculpture in Islamorada, Florida

Betsy, the world’s largest lobster sculpture in Islamorada, Florida

Of course, you can’t miss a photo with the giant lobster sculpture at Rain Barrel Village, right off the scenic A1A. The village also has over an acre of shops and gardens, so spend some time exploring.

Key Largo: Marina del Mar and Waterfront Fun

We needed a night in Key Largo before continuing on our road trip, so we booked a budget-friendly room at Marina del Mar Resort & Marina.

I wasn’t sure what staying in Key Largo, the northernmost city in the Florida Keys, would be like, but we ended up loving it. Key Largo is laid-back and all about life on the water. Even the resort where we stayed was seamlessly integrated with the surrounding marina. I couldn’t stop taking photos of the colorful boats.

Marina del Mar resort grounds

Marina del Mar resort grounds

Our no-nonsense room, which included a mini fridge, suited our needs well. They also have suites with full kitchens and living rooms if you want more space. There’s a pool as well and, more importantly, free breakfast.

Fill up because there’s lots to do in Key Largo with kids:

Day Trip to Miami From Key Largo

Key Largo is about an hour south of Miami, so you can easily drive into the big city for the day.

Two fun places to visit in Miami with kids are Deering Estate and the Fairchild Tropical Botanic Garden. Both offer acres of green space for kids to expend some of that energy from being cooped up in the car while adults and teens will appreciate the beauty.

Fairchild Tropical Botanic Garden

Part of the Children's Garden at Fairchild Tropical Botanical Garden

Part of the Children’s Garden at Fairchild Tropical Botanical Garden

Fairchild Tropical Botanic Garden boasts over 23,000 plants on 83 acres, a vast wonderland for families to discover. Kids can even become a “certified explorer” by completing special missions.

While there’s much to see — a sunken garden, a palm savannah, bamboo and flowers galore — our favorite was the conservatories. With Chihuly glass art, thousands of butterflies and florid greenery, it’s gorgeous.

They also host events throughout the year. Right now, you can experience the garden transformed after dark with NightGarden. A refreshing break from Christmas lights, this interactive spectacular features a talking tree named Archie who has his own Instagram, an augmented reality hunt for fairies, faux snow, fog bubbles and more.

Archie The Talking Tree about to sing a song on request (from a kid) at NightGarden

Archie The Talking Tree about to sing a song on request (from a kid) at NightGarden


NightGarden is great for families, too. Kids can climb in the Children’s Garden to trigger sound effects, build with glowing blocks, and wander through the Rainbow Forest. (And if you have a little one who loves fairies, this will be the highlight of the trip.)

Deering Estate

Deering Estate

Deering Estate

Another attraction on beautiful Biscayne Bay, Deering Estate is a 1920s historic landmark in a pristine natural setting. Explore the tropical hardwood hammock and forget you’re in the city. You might even spot manatees in the boat basin — we did!

The estate also includes two historic buildings you can tour. They’re filled with art, artifacts and other wonders like the jawbone of a dire wolf excavated nearby. Check their calendar before you go because there are special events throughout the year, ranging from concerts to campfires.

Tip: Restaurants are just down the road. You can pick up lunch and get free same-day re-entry to the estate, where there are picnic tables near the water. The view can’t be beat!

For more to do in Miami and farther up the coast, check out our road trip guide from Palm Beach Gardens to Miami.

About the Author

Cheryl Rodewig is storyteller, marketer, and award-winning feature writer specializing in travel. Her Venn diagram includes minimalism, waterfalls, French, and the em dash. Find her at cherylrodewig.com or on Twitter at @cherylrodewig.