Sample island life on this weekend road trip down the Overseas Highway. In just two days, you'll have the opportunity to snorkel a living coral reef, kayak through mangroves, and feed giant tarpon. You don't need to use your vacation days to experience the Florida Keys.


  • Kayak, SUP, or jet ski through mangrove channels
  • Snorkel North America's only living coral reef
  • Try your hand at deep-sea sportfishing

Brief Itinerary

Day Highlights Overnight
Day 1 Key Largo and Marathon Key Islamorada
Day 2 Explore Islamorada by Land and Sea  

Detailed Itinerary

Day 1: Key Largo and Marathon Key

A beach on Key Largo
A beach on Key Largo

You’ll head south out of Miami on the Ronald Reagan Turnpike to US Highway 1 (also known as the Overseas Highway), one of the most scenic roadways in the country. Another option is to take the quieter route along Card Sound Road, which connects the mainland with the top half of Key Largo. More off-the-beaten-path than the main highway, Card Sound Road is lined with mangroves and locals selling blue crabs and won't add any additional drive time to your trip.

This morning, you’ll be exploring Key Largo, home to John Pennekamp State Park ($8 entry per vehicle). Located at Mile Marker 102.5 on the ocean side of the highway, here you’ll find the oldest underwater preserve in the continental US, home to one of the world's living coral reefs. There are a number of ways to take in the beauty here - walk the trails through tropical hardwood forests, kayak or SUP through the mangrove swamps, snorkel over the Spiegel Grove shipwreck, or board a glass-bottom boat over the reef. If you have the necessary certification, you can even scuba dive. If you’d prefer to stay on land, you can walk the trails (Wild Tamarind Trail is a short and easy loop, while the Mangrove Trail takes you on a boardwalk to an observation tower) or hang out on one of the park’s beaches. Cannon Beach is better for snorkeling close to shore, while Far Beach is great for swimming and offers more shade for relaxing under the palms. 

Dine at the Fish House for lunch (try the fish of the day matacumbe style) before heading to Marathon Key, another 60 minutes further south along US 1.

Along the way, stop at Robbie's Marina (on the right at Mile Marker 77.5) for a chance to feed a giant tarpon before arriving in Marathon. Keep an eye out for the pelicans - they'll steal the bait right out of your hands! 

On the north end of Marathon Key sits the Dolphin Research Center (Mile Marker 59), where visitors can interact with and learn about the dolphins and sea lions that live there.

Further south on the island is the Turtle Hospital (Mile Marker 48.5), a rehabilitation center for injured turtles. You can sign-up for a tour of the hospital to learn about their flippered residents and have the opportunity to feed sea turtles.

If you’d prefer to spend the afternoon outside, Sombrero Beach is a beautiful stretch of white sand just off US 1. Take a left at Mile Marker 50 on the Atlantic side and follow Sombrero Beach Road to the end, where you'll find free parking.

Head back up US 1 to Islamorada for a toes-in-the-sand dinner at the Morada Way Beach Cafe.

Day 2: Explore Islamorada by Land and Sea

Anne's Beach on Islamorada
Anne's Beach on Islamorada

For a sit-down breakfast, try Midway Café & Coffee Bar, where you’ll find a big menu of omelets, waffles, and breakfast burritos. If you prefer breakfast to-go, grab a cinnamon roll from Bob’s Bunz on your way to the marina.

Islamorada is known as the sportfishing capital of the world, so it’s only fitting that you head to sea on a fishing charter this morning. You’ll try your hand at reeling in a hogfish, snapper, grouper, or maybe even a mahi. The crew will help you every step of the way.

If you’re not an avid angler, another way to explore the aquatic surroundings is by renting a Waverunner; you can zip around the high seas, cruise the mangrove tunnels, and motor out to smaller islands and the ‘secret’ sandbar off Whale Harbor, a local favorite (try to avoid the sandbar if you visit on the weekend, as this is when it is busiest). 

Back on shore, you’ll find the Green Turtle Inn, featured on the Food Network and famous for the Key lime pie, a great place to stop for lunch.  From there, take a stroll through the 6-block corridor of the Morada Way Arts & Cultural District. Here you'll find galleries, shops, restaurants, and art studios along the only 'Main Street' between Miami and Key West. For those not driving (and of age), visit the beer garden at the Florida Keys Brewing Company for a tasting flight of local beers.

If you'd prefer to spend the afternoon lounging in the sun, head to Anne's Beach (parking at MM 73.4), voted as one of the Best Hidden Beaches of South Florida by Lonely Planet. The waters here are too shallow for swimming but are perfect for wading or strolling along the sands.

From here, it’s only a 90-minute drive back up to the city along US 1.