2026
Florida: Florida Keys with Bike Paths (October 4-9, 2026) 6-days/5-nights
Hotel to hotel - Bicycling to the destination hotel each day
▶️Quick Book
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This was the very first Vacation Bicycling tour. The Florida Keys was consistently one of the most popular and well liked, so we thought it was time to bring it back and reimagine the bicycle tour to make it even better!
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We are staying at just one hotel and starting the trip in the heart of the Florida Keys. We will ride each route just one direction and enjoy a "free day" in Key West.
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Ride on 90 linear miles of existing paved bicycle trails within the 100+ miles of the Keys trail riding from Key Largo to Key West
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We ride with clear ocean water on one side and the gulf on the other.
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We experience all The Florida Keys & Key West with a blend of Caribbean blue waters, tropical foliage, stunning sunsets and the unique city that is Key West.
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Also, we only have two real hills on the entire ride, which technically are not hills but two bridges, the 7-mile Bridge and the Channel #5 Bridge.
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You can visit the Dolphin Research Center and get into a splash war with one of the dolphins; be careful, you may lose the splash war to a dolphin in the experience, but what a great story!
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Of course, we will take time to relax in a hammock, enjoy beautiful sunsets and take home amazing photos and memories.
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The Florida Keys is a great warm southern finale to the bicycle riding season!
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Come enjoy a relaxing vacation while experiencing the unforgettable adventure of biking the Florida Keys.
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Most importantly the Keys are flat with the only hills the few raised bridges. For the entire 100+ miles of riding only 182 ft of descent and 1885 ft of descent:
Pricing options:
Economy $1999 per person/double occupancy (single occupancy +$550)
✔️Lowest price
✔️Pay Now
✔️No changes
✔️Non-refundable
✔️Limited price availability
Standard/Signature $2249 (the old-fashioned way*) per person/double occupancy (single occupancy +$550)
✔️Pay $200 deposit now
✔️Pay balance 45 days before trip start
✔️Full Credit for future trip for change or cancellation up to 60 days before trip start
✔️*This is the exclusive pricing way that Vacation Bicycling used for 18 years through 2024
Premier $2749 per person/double occupancy (single occupancy +$550)
✔️Pay with credit card or debit card
✔️Fully refundable/changeable up to 15 days before trip start
✔️No change fees
✔️Pay Now
Day 1, Sunday
Check into the hotel throughout the day. The Florida Keys are so beautiful. The main mission on arrival is to begin to relax and enjoy the Keys. In the evening meet new and old friends during the Get Together scheduled for 4:00pm and then dinner.
Lodging:
Hampton Inn Key Largo Florida Keys
Marathon, Florida
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Internet
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Outdoor swimming pool
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Hair dryer
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Fitness center
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Coin laundry
Featured Group Dinner — A special evening meal hosted for the group:
Hobo's
Hobo's
Key Largo, Florida
Selections include:
- Key Lime Style fresh catch of the day - House speciality. Lightly dusted and pan seared, topped with fresh tomatoes, scallions, Parmesan cheese and homemade Key Lime butter sauce.
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Shrimp Hobo - Sautéed jumbo shrimp in butter, garlic, shallots, wine, mushrooms, scallions & tomatoes. Served over pasta or rice.
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Burgers - include choice of Seasoned Waffle Fries or homemade Cole Slaw. Substitute House or Caesar Salad add 4. Substitute sweet potato fries, baked mac and cheese or asparagus add 4.
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Filet Mignon 8 oz. - The iconic cut of beef grilled to perfection.
Day 2, Monday
Key Largo to Marathon
Begin our ride at the start of the Florida Keys Overseas Heritage Trail. You will start on the Bike Trail near the hotel and John Pennekamp Coral Reef State Park then proceed on paths through the first city in the Florida Keys, Key Largo. Later you will also ride on the Channel #5 bridge with the beautiful Gulf waters on one side and the shimmering Atlantic waters on the other. On your journey take a moment to see and/or take a picture of Betsy, the World's Largest Lobster. Sculptor Richard Blaze spent five years building Betsy. In Islamorada watch Tiki statues and wood carvings being made and maybe even choose the perfect Tiki to have shipped home. Finally, about half-way you will stop at the most visited tourist destination in the upper Keys, Robbie’s, which is a tourist's paradise with lots to do and voted #1 Place in the Keys with fish feeding, restaurants and tourist attractions. Take your pick: Shop, Feed the Tarpon, have an ice cold drink or lunch in view of the ocean. Make it your perfect adventure. Then continue to your next hotel in Marathon.
Bicycling route: 49 miles, biking from Key Largo to Marathon. [Most of the route is on dedicated bike paths. The route is flat.]
Breakfast: Provided by hotel
Lodging:
Fairfield Inn Marathon Florida Keys
Marathon, Florida
Evening meal: At your leisure - discover a great local spot
Day 3, Tuesday
Marathon to Key West
Enjoy what will become your lifelong memory of bicycling over 7-mile Bridge. It is famous. Why you ask? Enjoy your day like many movie stars have done in the Florida Keys. Many films have been filmed on 7-Mile bridge, including the blockbuster film, "True Lies" written and directed by James Cameron, starring Arnold Schwarzenegger, Jamie Lee Curtis and Bill Paxton. In addition to the fame from all of the filming on the bridge, you should also take a leisurely day to bicycle over one of the greatest and most beautiful rides that you will always remember on the old 7-Mile bride. Also, take a stop at Bahia Honda State Park ($2.50 entrance fee) with beaches that are ranked among the best in the world. You can even catch a snorkel tour while visiting the park. Of course you can also ride directly to the hotel and relax with a cool drink while enjoying the pool. View the ocean, go for a swim, or just relax watching the waves or explore Key West.
Choose which unique Key West restaurant to have lunch and/or dinner. Once downtown, you can catch a ride on the Old Town Trolley or the Conch Train to get an overview of the history and sights of Key West. As you visit Key West enjoy a bite to eat at the many restaurant choices including Jimmy Buffett's Margaritaville or Sloppy Joe's Bar to name but a couple of the hundreds of nationally acclaimed restaurants in Key West. Of course you can also enjoy the shopping along Duval street which features every type of store and gallery. nationally acclaimed unique restaurants and pubs. In the evening visit the world famous Mallory Square to watch the street performers and later the beautiful sunset.
Bicycling route: 54 miles, riding from Marathon to Key West. [Most of the route is on dedicated bike paths. The route is flat.]
Breakfast: On your own - perfect time to try that restaurant you've been eyeing!
Lodging:
DoubleTree Resort Grand Key Key West
Marathon, Florida
- Internet
- Outdoor swimming pool
- Hair dryer
- Fitness center
- Coin laundry
Evening meal: At your leisure - discover a great local spot
Day 5, Thursday
Key West to Marathon
Today we start our ride from Key West, where "Everything Old is New Again." Enjoy the sights and unique culture of the country's southern most location, visit the palmtree lined streets and discover gingerbread mansions and tin-roofed conch houses. After enjoying the sights of Key West we leave the city on dedicated bicycle paths. Then we make a stop at Baby's Coffee the locals favorite coffee shop. Continue heading north, exploring and visiting unique sights of the Keys as you ride along and near the Atlantic Ocean and the Gulf of Mexico. Take time to stop for lunch at No Name Pub, one of the most uniquely decorated restaurants in the world. Ride through Key Deer country. The miniature Key Deer only live in the Florida Keys. Take some great photos to show your friends.
Bicycling route: 54 miles, riding from Marathon to Key West. [Most of the route is on dedicated bike paths. The route is flat.]
Breakfast: On your own - perfect time to try that restaurant you've been eyeing!
Lodging:
Fairfield Inn Marathon Florida Keys
Marathon, Florida
Evening meal: At your leisure - discover a great local spot
Day 5, Thursday
Marathon to Key Largo
Start today where we left-off yesterday. Continue riding by and near the sparkling ocean water. Take a stop at Long Key State Park ($2.50) a 65-acre protected area of historic sites, wild flowers and tropical trees. Kayak, canoe or hike through Long Key State Park before continuing on your ride. Ride atop The Channel Two Historic Bridge, Long Key Historic Bridge, Long Key Historic Bridge, Tom's Harbor Historic Bridge and Tom's Harbor Channel Historic Bridge. All have been converted to bicycle bridges. Bicycle by or take a stop at Curry Hammond State Park, the largest undeveloped parcel of land between Key Largo and Big Pine Key. In addition Curry Hammock provides vital habitat for many local and migrating species and hosts record numbers of peregrine falcons every fall. Get back to Marathon and enjoy the outdoor pool at the hotel or the sandy beaches of Sombrero Beach.
Bicycling route: 49 miles, biking from Marathon to Key Largo. [Most of the route is on dedicated bike paths. The route is flat.]
Breakfast: On your own - perfect time to try that spot you've been eyeing!
Lodging:
Hampton Inn Key Largo Florida Keys
Marathon, Florida
- Internet
- Outdoor swimming pool
- Hair dryer
- Fitness center
- Coin laundry
Featured Group Dinner - A special evening meal hosted for the group:
Mrs. Mac's Kitchen (Big)
Mrs. Mac's Kitchen (Big)
Key Largo, Florida
Selections include:
- Mahi (fish of the day) - Grilled fresh fish topped with Mrs. Mac's signature homemade Tijuana sauce, stewed from tomatoes, tomatillos and jalapeños with fresh cilantro and onions.
- Blackened Mahi Tacos - Blackened Mahi, pico de Gallo, Colby jack cheese, guacamole and cabbage on flour tortilla.
- Burgers - 1/2 pound made fresh and char grilled and served with fries, including house specialty burgers: Blackened Bleu Cheese, Backyard Bar-B-Q and Bahama Burgers.
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Chicken Breast - Char grilled, oven roasted or blackened and served with your choice of side and homemade slaw or garden or caesar salad.
Day 6, Friday
Ride and explore the Keys one last time before starting your journey home.
Breakfast: Provided by the hotel.
Please note all trip information is based on previous trips and/or contracted lodging and restaurants and is subject to change based on availability or specific trip needs.
Riding difficulty:
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Riders who are comfortable riding at least 10 miles per hour should have an enjoyable trip. The routes are primarily on bike paths with a little riding on bicycle designated or low traffic roads. Please see the daily routes descriptions for additional information. Of course, if a rider is tired or does not feel like riding, the SAG vehicle will transport the rider to the hotel. All riders may ride at their own pace, slow or fast or anything in-between.
Arriving by Automobile:
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Drive to the Hampton Inn Key Largo
Arriving by Plane:
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Fly into Key West International Airport (EYW); or fly into Miami International Airport (MIA). Then rent a car or take the Keys Shuttle 305-289-9997 to the starting hotel.
Deposit:
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$200 to reserve your spot and the remainder due 45 days before the trip start.
What is Included:
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Hotel lodging
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Ride Packets with Cue Sheets (directions)
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Garmin/GPS routes to download
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Google Maps routes for your iPhone or Android Phone
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Fully sagged including van transportation and rider assistance.
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Breakfast most mornings (see above)
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Happy Hours (BYOB) on selected evenings
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Dinner with the group two evenings (see above)
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Great riding, scenery, fun and enjoyment!
Bicycles:
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Most participants bring their own bicycles
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To ship your bike, we would suggest using shipbikes.com or bikeflight.com for shipping. To ship your bike to the hotel: Hampton Inn Key Largo
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If you fly, most major airlines including Delta, American, United and Alaska Air now waive the oversize fee for bicycles (sporting equipment) and just the standard luggage fee applies. Please contact your airline for all the details.
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Bike Rental: Bikes are available for rent in the Florida Keys. We suggest conducting a Google search to find the best place to accommodate your needs.
Weather in October for our trip biking area in the Florida Keys:
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Average High 86°