Florida Keys

Sunshine State Splendor
Chris Register
Price :
Surface :
Duration :
10 days
Support :
Self Contained
Difficulty :
Level 2

Get a second dose of summer with this Sunshine State ride. You can smile wide as you ride knowing you’re enjoying 300 miles of sunny, warm weather!

This unique loop ride takes in Florida’s largest city, longest bridges, and wildest swamplands, showcasing the best of South Florida along a pair of Adventure Cycling 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.

Photos by Paul Kingsbury | Wasin Pummarin | Paul Kingsbury
Oct 28 - Nov 06, 2023
Almost full, 3 spots remaining

"It was great to meet people from different places and experiences who are all drawn to touring. Having that common thread put us all at ease right away."


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

Today, as a special treat, we'll shuttle to the eastern reaches of Everglades National Park. Before heading out, though, we might want to get our bearings at the Ernest Coe Visitor Center, located just outside Florida City in Homestead. In the park proper, we'll find a series of walking trails (the Pa-hay-okee Overlook Trail features an observation tower that's a great place to spot native birds). The area encompassing Everglades National Park, now the largest subtropical wilderness in the U.S. and a designated International Biosphere Reserve, was inhabited largely by the Calusa Indians prior to the arrival of the Spanish in 1513. Thought to have first emerged around 1000 BC, the Calusa were a highly organized society that left behind tools made of shells and wood, architectural shell works, and evidence of canoe trails.

Day 6. Florida City to Key Largo, 27 miles

After today's introduction to cycling in the Keys, we'll overnight at John Pennekamp Coral Reef State Park, where the campsites surround the eastern side of Key Largo. Scuba tours and glass-bottom boat tours are available, the visitor center features a 30,000-gallon saltwater aquarium teeming with life, and a theater shows nature videos.

Day 7. Key Largo to Marathon, 43 miles

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.


Additional Details
Start Location:
Ft Myers, FL
End Location:
Ft Myers, FL
Southwest Florida Intl. (RSW)
Total Days:
Riding Days:
Layover Days:
Tour Leader:
Average Daily Mileage:
Shared cooking
Level 2
Restricted Bike Type:
eBike, eTrike