Florida Keys Cycling

Florida Keys Cycling

January 26 - February 1, 2019

(7 days, 6 nights; Sat - Fri)

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Double Booking


Single Booking


Roommate Rebate


Includes all lodging, breakfasts, dinners, leaders, snacks, support van, park entrance fees, airport transfers, ferry transfers, tour maps and narratives.

Assembly Point

Ft. Lauderdale, Fl

Timberline van shuttle is included from Ft. Lauderdale to the start of the tour, and from Fort Meyers to the Southwest Florida International Airport following the tour.

Not Included: Airline Service; Guide Gratuity.

Meeting Time

Fort Lauderdale-Hollywood International Airport 3 pm, Hotel 3:30 pm

Drop-off Time

Southwest Florida International Airport, 4 pm

Ready for a spectacular February ride in 70 degree weather?  We have found an ideal ride, call it early season or winter getaway, to hold your attention, with enough quirky sideshows to keep you amused.  We will ride the entire 113 mile length of the famed Overseas Highway from Key Largo to Key West, and then cruise to Fort Meyers from Key West on a modern, luxury catamaran and from there ride Sanibel and Captiva Islands. These islands are a special place whether it is your first time to the famous islands or you are a regular. Sanibel Island is the perfect place to stroll by the lighthouse or enjoy a trip through Ding Darling wildlife preserve looking for amazing animals and birds. The tour is also ideal for couples or those who might want a beach vacation without actually lying around on a beach.  As with all our bike tours, e-bike rental is also now available.

In riding the Keys, we discovered some truths: the ocean and Gulf are as wide and at least as blue as Montana’s Big Sky; as deep as the Rockies are high; the coral reefs of the Keys rival the color country of Utah’s canyons and its wildlife is as fascinating as that of Yellowstone. Palm trees and mangrove swamps and tropical orchids are the wildflowers of the Keys; crocodiles and manatees and the occasional panther are the protected wildlife. In the West we have Bear Valley and Death Valley; in the Keys there is Shark Valley. Road signs in the West warn of elk or deer crossings; in the Keys are alligator warnings; river valleys in the Keys are rivers of grass and snorkeling or kayaking replace hiking as offered activities on layover days.  In short it reinforces what we all know-there is no part of America that is not special and glorious.  This is a unique and beautiful tour and we are excited to be offering a Florida Keys trip.

Our assembly day is in Fort Lauderdale, FL , where we will meet, fit the bikes, and enjoy our orientation dinner.  On Day 2 the van will shuttle us to Everglades National Park to ride the 15-mile Shark Valley Scenic Loop as a warm up.  The route goes to the Shark Valley Observation Tower where sweeping views of the Everglades are possible.  We then continue to Key Largo by van.  There may be an opportunity for a visit to John Pennenkamp State Park with kayaking or snorkeling options before our overnight in Key Largo.

Day 3 begins with an optional shuttle to the eastern end of the Overseas Highway.  The 113 mile route carries US Highway 1 to the southernmost end of the continental US and Mile Marker 0. This thin strand of highway connects the Florida Keys which has more than 1700 islands and more than 46 bridges connecting them. A paved bike path parallels the highway for much of the distance. About 20 miles out of Key Largo, beautiful views of both the Atlantic and Gulf open up, and at times there are only a few hundred yards separating these two bodies of water. There are multiple bridge crossings and multiple attractions along the way. This is an exotic journey through a spectacular land that includes the largest area of coral reef in the mainland U.S. and it is home to crocodile, deer, manatee, and the occasional panther. There is even a turtle hospital in Marathon that is open to visitors. The bike route is a mix of paved bike paths, shoulders and back roads. Our overnight destination tonight is Marathon.

On Day 4 our ride includes the famous 7 Mile Bridge, so don’t forget to wave to Fred the Tree at the far end of the bridge. Additionally, we ride past Bahia Honda State Park with a beautiful natural beach, and a stop on Big Pine Key which is home to the Key Deer Refuge. as we make our way to the 0 Mile Marker and our overnight in Key West.

It’s a free day in Key West on Day 5. Some of the world famous attractions include: all things Hemingway; Truman White House; Mallory Square for the sunset tradition; all the zany happenings on Duval Street and of course untold eating opportunities. Is it touristy, but there is elegance and history to be found in its Old Town and the diverse cultures and lifestyles so celebrated on the Island make it a wonderful, joyous place. The natural beauty, beaches, gardens, and stunning ocean views all combine to make this a magical experience. At 6 in the evening, we catch a ferry ride to Fort Myers where we will spend the night.

Day 6 affords a startling, dramatic and unbelievable change of pace as we ride early in the morning to the untouched barrier islands of Sanibel and Captiva. Accessible by a 3 mile causeway from Fort Myers, Sanibel Island has been determined to maintain a pristine natural environment. Over half the Island is protected against development and no building can be higher than a palm tree.  More than 35 miles of bike paths and walking paths connect the world famous beaches, renowned for their seashells, The island is home to the Ding Darling Wildlife Refuge, which is a major shelter for migratory birds. Connected to Sanibel by a small bridge is Captiva Island, home to the Calusa Tribe, and possible playground to pirates in another time.  The Island is steeped in history and intrigue. It is possible to ride to the end of the Island and explore miles of scenic drives before ending in “downtown ” Captiva. These islands are tropical wonders that evoke feelings of isolation and remoteness found in very few places in the US.

We return to Fort Meyers on Day 7, riding the paths and roads back across Captiva and Sanibel Islands, finding new beaches and attractions to round out our unique Florida Keys cycling Tour.




Day 1Assembly, bike fitting, orientation dinner, Fort Lauderdale, FL
Day 2Shark Valley Scenic Loop. Van shuttle to Key Largo.15
Day 3Key Largo to Marathon.50 - 63
Day 4Marathon to Key West51
Day 5Free day in Key West, evening ferry ride to Fort Myers.
Day 6Sanibel and Captiva Island cycling. Overnight in Captiva.40
Day 7Return to Fort Myers.40

Total Distance: 196 miles

Inn Highlights

  • Sea Dell Motel
  • Tween Waters Islands Resort

Florida Keys Cycling

January 26 - February 1, 2019

(7 days, 6 nights; Sat - Fri)