Florida Key West Bike Tour

Ride from Key Largo to Key West on the famous Overseas Heritage Trail, spanning 42 bridges with turquoise waters on both sides. Pedal through colorful island towns and cross the old Seven Mile Bridge to Pigeon Key. Spend three nights in Key West, explore the lively streets, Mallory Square sunsets and visit Hemingway’s iconic home.

Day 1: We will start by crossing the Atlantic Intracoastal Waterway over the Card Sound Bridge. Following the Florida Keys Overseas Heritage Trail as much as we can, as well as along the shoulder of the famous highway 1, we will make our way through Key Largo to Islamorada. Islamorada is recognized for its fresh seafood and vibrant arts scene at the Morada Way Arts and Cultural District.

Day 2: After breakfast, we will shuttle to Little Duck Key to begin the ride along the Overseas Heritage Trail. Along the way, where bridges are closed due to damage, we will jump on to the wide shoulder of Highway 1. Biking through many keys, including Summerland Key, Sugarloaf and Lower Sugarloaf Keys, Rockland Key, and Stock Island, we will arrive in  Key West for the next three nights.

Day 3: What Key West lacks in size (it’s roughly four miles long and less than two miles wide) this little island makes up for in character: fresh seafood, breathtaking sunsets, and waterfront dive bars. Key West is a study in contrasts, and this itinerary mixes the can’t-miss landmarks with quiet respites in nature, literary history with the island’s famous tangy dessert, and upscale elegant eats with down-home dive bars.

After biking around the island, you will have the rest of the day to explore on your own or to just relax at the hotel pool and poolside bar. You are on vacation after all.

Day 4: After a great breakfast, we’ll ride our bikes over to the Hemingway House to take a tour and then visit Key West Museum of Art & History at the Custom House. After some time on your own for relaxation or to visit the places you might have missed, we’ll meet up for a sunset cruise.

Day 5: Biking along the 7-mile bridge and finishing the day with a visit to Robbie’s to feed the tarpons makes day 5 an exciting challenge.

Day 6: For our last day, after breakfast, we’ll hop on the bikes heading north toward Miami from Key Largo through the Southern Glades Wildlife and Environmental Area. We’ll stop by some beaches on the way up to make sure we soak in as much sun as possible on our last day. After lunch at the The World’s Best Fruit Stand, our shuttle will take us back to where it all began in Miami.