Escape the frigid confines of winter this year with a warm, mellow tour in the Sunshine State, and let our van do the heavy lifting! This ride showcases the best of South Florida along one of Adventure Cycling’s finest routes.
You’ll start in Fort Myers, see the modern quaintness of Naples, and enjoy the down-home quirkiness of Everglades City. From there, prepare to be enamoured with the majestic swamplands as we ride the Tamiami Trail Road to be enveloped in Big Cypress National Preserve. Not long after that, you’ll find yourselves spanning Florida’s longest bridges hopping from key to key until your soul reaches full Parrothead for a celebration in Key West. A sunset ferry ride back to Fort Myers will close out this glorious loop of all the diverse adventure South Florida has to offer.
Our 2022 departures have already taken place, check back for future dates.
"I enjoyed the opportunity to try something totally different, the freedom to be riding along watching the world go by from a new perspective."
Day 1. Fort Myers, 0 miles
We'll gather in the bright and lively Fort Myers, a tourist gateway to southwest Florida and known winter respite of Thomas Edison, Henry Ford, and other influential Americans. If you arrive early enough, you'll have time to see sights named for these folks before gathering with your tour group and preparing for the ride ahead.
Day 2. Fort Myers to Naples, 45 miles
We'll roll out on our first day down Estero Boulevard, soaking in the sea spray as we hop from key to key before turning slightly inland toward Naples. Known for its world-class shopping, sophisticated dining, and wealthy country clubs, we'll be basking in the upper-class radiance that is Naples before settling down to camp for the evening.
Day 3. Naples to Ochopee, 51 miles
We kick off today's ride on Route 41, or the Tamiami Trail. The Tamiami is a beautiful stretch of pavement that travels through various forest preserves including Big Cypress. We'll witness the wonderful charm of old-world Florida that is Everglades City, an interesting juxtaposition from Naples. Continuing on the Tamiami through Ochopee, we'll rest at a campground in the heart of Big Cypress National Preserve.
Day 4. Ochopee to Florida City, 68 miles
Didn't get enough of the lush envelopment on Tamiami? You're in luck! The first half of today will be spent still in the warm embrace of this natural area before we turn south. Our travels will take us through agricultural areas with many fresh produce stands and orchards. We'll end a big day's riding in Florida City, thankful to have a rest day here awaiting us!
Day 5. Florida City, 0 miles
Layover day. We'll spend the day relaxing in Florida City, a suburb of Miami and the southernmost city in the U.S. that's not on an island. Feel free to explore the shops and restaurants, or if you're feeling adventurous, you can go on a tour in the Everglades. Keep an eye out for alligators!
Day 6. Florida City to Key Largo, 27 miles
Can you hear that Beach Boys tune yet? It's our first day in the Keys! We'll enter through North Key Largo, with Key Largo Hammock Botanical State Park to your left and Crocodile Lake National Wildlife Refuge to your right. You'd do well not to get those confused lest you want to become dinner!
Day 7. Key Largo to Marathon, 43 miles
We'll hop enough keys today to fill a janitor's key ring. Today the Overseas Highway leads us through Islamorada, Indian Key, Long Key State Park, and, finally, Marathon. We'll ride across several of the relatively new, bike-friendly bridges that link the Keys. Other available highlights of the day include the Theater of the Sea in Islamorada, where you can swim with dolphins, sea lions, and rays. Options on Long Key include canoeing through a chain of lagoons or hiking the Golden Orb Trail. Our destination, Marathon, occupies several of the central Keys. It was named by Florida East Coast Railroad workers who toiled at an unrelenting pace to complete the railroad — a real marathon of a job.
Day 8. Marathon to Key West, 57 miles
We'll cross the New Seven Mile Bridge to Bahia Honda State Park on Big Pine Key. The 500-acre park features lovely sand beaches and some of the best snorkeling and beachcombing in Florida. Sea kayaks are also available for rent and make a great way to explore the quiet waters off the key. From there, we'll continue on to Key West, which has been likened to a more laid-back version of New Orleans. Originally known as Cayo Hueso, Spanish for "bone key," it's said that the island was so named because early European visitors found it to be littered with human bones.
Day 9. Key West, 0 miles. Layover day
There's so much to see and do in Key West that just one layover day can't do it justice. Still, you can give it your best shot. There's the Key West Aquarium (built by the Works Progress Administration in 1932–34), Mel Fisher's Treasures (exhibits from shipwrecks discovered by the famous treasure hunter), the Ernest Hemingway Home and Museum, the Harry S. Truman Little White House, the Key West Lighthouse, the Half Shell Raw Bar — you get the picture. Tonight we'll have our celebration dinner. Has anyone seen my lost shaker of salt?
Day 10. Fort Myers, 0 miles
Today's the day we say goodbye. Though we've only boated around the tip of Florida, we hope you'll return to the mainland with plenty of stories to tell and an island state of mind. Enjoy one more afternoon in Key West before boarding the ferry as a group. We'll make our way back to Fort Myers via ferry, then spend our last night together in Florida.