Bike Tour | Florida Keys 2018-03-07T19:23:21+00:00

Florida Keys Tour


Great news!! Our guides returned November 4 from four days of careful and thoughtful Florida Keys “post-Irma” exploration, and we are delighted to report that our tours are a definite “go.”

Our guides’ report said it best –  “Azure blue skies, temperatures in the 80’s every day, and a breeze from the northeast accompanied us as we biked our adjusted bike route from Key Largo to Key West. In most parts of the Keys, we enjoyed a landscape that was seemingly untouched by Hurricane Irma. Of course, in a few specific areas we noticed damage to buildings and vegetation, and we have altered our route a bit to avoid a few sections of the bike path, and yet the wonderful people of the Florida Keys have done, and are doing, a fabulous job of cleaning up and moving on. Indeed, when we arrived in Key West itself, we found the entire area to be as lush and festive as ever, hard to see any hurricane effects at all. The Keys are definitely ready to provide a high quality bike touring experience.”​

Imagine. It’s the middle of next winter (remember winter?!), and you are basking in the bright sunny warmth and exquisite beauty of the Florida Keys, a string of beautiful islands connected by a series of causeways and bridges that ultimately take you to exciting Key West, the southernmost (and warmest!) point in the continental U.S.

This is a tropical paradise. You can enjoy the easiest of cycling, and immerse yourself in such pleasures as kayaking, paddle boarding, and swimming, while enjoying ample time throughout your tour to luxuriate in full relaxation – ease yourself into a lounge chair, take a dip in the warm ocean or a swimming pool, and enjoy an evening beverage at a poolside tiki bar.  The biking follows the paved Florida Keys Overseas Heritage Trail, meandering from island to island (30 in all) and we are often treated to views of the Gulf of Mexico on one side and the warm blue waters of the southern Atlantic on the other.

We help you make this the perfect winter escape by including stays at two exquisite resorts in the Keys and a quiet prestigious property in the heart of Old Town Key West. Our tour includes visits to a wide variety of sites, such as John Pennekamp Coral Reef State Park, the Dolphin Research Center, Robbie’s Marina (where you can feed the wild tarpon), and Long Key State Park. In Key West, we visit Ernest Hemingway’s old haunts and take a tour of his home and museum; tour the renowned Key West Butterfly and Nature Conservancy; visit Harry Truman’s “Little White House;” cycle out to the huge red buoy that marks the southernmost point of the continental U.S.; and are treated to a gorgeous sunset sail in Key West Harbor. Key West is, of course, rightfully famous for its off-beat character and nightlife, and if you wish, you may choose to browse the shops or take in the quirky night scene along Duval Street and the circus-like sunset celebration at Mallory Square. We also include a ride on the somewhat touristy but always interesting “Conch Train,” that takes you to many of the more famous attractions of the town. You will have a full day to explore on your own, taking in the sights, sounds, smells, and shops of Key West at your own pace.

Intrigued? See details on the day-to-day itinerary, where you stay, the weather, and the biking on the links below.

Florida Keys Tour Itinerary

SUNDAY | Arrival Day |  Key Largo:  Playa Largo Resort & Spa

Today we take full advantage of our stay at our luxury destination resort. Discovery Bicycle Tours will provide you with transportation from the Pullman Hotel near Miami International Airport to the luxurious Playa Largo Resort & Spa and get you there by early afternoon. After a fabulous welcome lunch of delicious tapas at their Sandbar Cafe, you can enjoy resting by the pool, dipping into the hot tub, or sunning by the sand beach. If you would like more activity on Sunday, you can partake in the resort’s various water sports (additional fees may apply) including paddle boarding, kayaking, snorkeling, catamaran sailing, or parasailing. Towards evening we will host a cocktail reception at the open-air Sandbar Café before enjoying a superb dinner at their romantic dockside “Sol by the Sea” dining restaurant.

MONDAY  | Key Largo: Playa Largo Resort & Spa

This is your vacation, so sleep in if you wish, or get up early to watch the bay reflect a sensational Florida Keys sunrise. After a leisurely breakfast, we will lead you on an easy get-acquainted ride to John Pennekamp Coral Reef State Park, the first undersea park in the United States. Following a beach side picnic we will treat you to a guided kayak tour of the Florida Keys National Marine Sanctuary along coral reefs, seagrass beds and mangrove swamps.

We arrive back at Playa Largo Resort in plenty of time to take to take advantage of the resort’s amenities, or best of all, just relax by the bay or by the swimming pool, and luxuriate in the warmth of south Florida.

Tonight we treat you to dinner at another one of the resort’s excellent on site dining rooms.

Biking: 11 miles. Easy (plus 2 hour kayak adventure)

TUESDAY | Marathon: Tranquility Bay Beachfront Hotel and Resort

After another leisurely breakfast, we have a brief van transport and then are back on our bikes riding south along a series of narrow causeways. We cross several of the keys in the middle chain such as Conch Key, Long Key, Fiesta Key and Lower Matecumbe. On either side of you, and for miles ahead, are the emerald waters of the Florida Sound and Atlantic Ocean. We stop to feed the tarpon at Robbie’s Marina a famous old-style marina and fish shack immortalized in paintings by dozens of artists and photographers. The marina has a number of open air shops and galleries but is best known for the large schools of majestic silver king tarpon that cruise to their docks and can be hand fed with small bait fish offered to the visitors.

The afternoon includes stopping at Long Key State Park to learn more about the mangrove estuaries plus a fascinating visit to the Dolphin Research Center where we can get up close to dolphins and sea lions and learn about some of the amazing research being done. Tonight’s destination is Tranquility Bay Beachfront Hotel and Resort, another luxurious bay side property. Much of your time here will center itself around water, whether in it, on it or lounging around it.  There is a lovely sandy beach for swimming as well as three pools for your pleasure scattered among the 12 acres of lush, landscaped gardens. This evening we will enjoy award-winning dining at their Butterfly Cafe, possibly followed by a celebratory night cap sitting beach side at TJ’s Tiki Bar.

Biking: 20 miles (with 10 mile option) Easy

WEDNESDAY  | Key West: Key Lime Inn

Today we begin with a van transfer through Marathon and across Seven Mile Bridge to our start on Summerland Key. We then cycle from Key to Key and include a welcome stop on Sugarloaf Key at the iconic “Baby’s Coffee”. Here we can indulge in a snack and maybe the locally roasted coffee before finishing our ride into Key West. Key West is literally the end of the road…you are at the southernmost point in the continental U.S. (closer to Cuba than Miami) and to go any further you will need a boat!  And yet its geographical location is only part of its world-famous attraction. You will ride along its palm-tree-lined streets, pass gingerbread mansions and tin-roofed conch houses, and later visit the homes and neighborhoods where Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost, Jimmy Buffett and Harry Truman all lived. And while Key West is famous for the night life and shenanigans of Duval Street (all true), you will also be impressed that it is not just a party town but is likewise a tightly knit community of permanent residents who cling fiercely to their live-and-let-live attitude.

Our home for the next two nights, the historic Key Lime Inn, is perfectly situated in a quiet location in Old Town and yet just an easy walk to all that makes Key West such a sought-after destination. Rooms are located among several buildings spread out on an acre of grounds, giving the property a very tranquil, laid-back Caribbean feel.  We will treat you on arrival to a catered lunch served on the deck beside their heated pool. In the afternoon you can take an optional guided walk to get acquainted with Key West, often meandering along Duval Street and Mallory Square before arriving at the harbor docks in time to take a spectacular sunset sail complete with complimentary hors d’oeurves and a celebratory glass of champagne. After your sunset sail you are on your own for dinner selecting from numerous excellent restaurants or maybe just opting for some bar food while enjoying the nightlife at one of Key West’s  legendary pubs or open air bars such as Sloppy Joe’s, the Green Parrot, or Hog’s Breath Cafe.

Biking: 15 or 25 miles

THURSDAY | Key West: Key Lime Inn

For early risers, morning can begin with a pre-breakfast “sunrise bike stroll” along the quiet streets before meeting up with the rest of the group to enjoy cinnamon brioche, eggs Benedict and other elegant fare at Croissants de France on Duval Street. After breakfast this morning, local celebrity Lloyd Mager will lead us on a special bike tour of “his” Key West. Lloyd’s fascinating off-the-beaten-track tour has been featured on Good Morning America, the Travel Channel and the New York Times and involves a ride along quiet streets and hidden lanes. There are many stops to sample tasty tropical fruit, smell delightful fragrant flowers and be entertained by Lloyd’s funny, wry and satirical insights into the “real” Key West.

After Lloyd’s ride, we have the option to board the very entertaining Conch Train which features a professionally narrated 90-minute tour taking you by many of the more famous (and infamous) places in Key West. Then you have many options to consider, including taking a stroll around town to visit the Southernmost Point, Harry S. Truman’s Little White House, Ernest Hemingway’s Home and Museum, Key West Butterfly and Nature Conservancy, Sunset Pier, and Mallory Square. Lunch is on your own, so if you are hungry or thirsty, try the Green Parrot Bar,  Kelly’s for Key Lime Margaritas, Mojito from Mr. Mojito (aka Jimmy) at Mallory Square, hot sauce tasting at Peppers, and please don’t leave without trying a locally made Key Lime Pie. It’s the best! Later in the afternoon we will gather for a cocktail reception followed by a gala farewell dinner celebration at Blue Heaven, certainly one of Key West’s finest (and funkiest!) restaurants.

FRIDAY | Departure Day

You can start today with an optional 7-mile sunrise bike ride which includes an out-and-back ride along the beautiful ocean bike path of Key West’s south shore, before we enjoy another bountiful breakfast at Banana Café.  Afterwards, there is a guided visit to the Butterfly Conservancy to enjoy some magical time amidst the tropical flora and fauna offered there, ending in time for us to get you to Key West Airport by 1 p.m. There are several afternoon flights from here to major hub airports along the East Coast.



Make your reservation with confidence. Your tour is completely 100% refundable up to 90 days of the tour date.

January 28 to February 2, 2018 – $3195 reserve
Reserve with $300 deposit

reserveFebruary 4 to 9, 2018 – $3195
Reserve with $300 deposit 

reserveFebruary 11 to 16, 2018 – $3195
Reserve with $300 deposit 

Final payment due 90 days prior to your tour (personal check, Visa, MasterCard, American Express or Discover)

Single Supplement Fee: $940*

Default Supplement Fee: $470*

*Single Traveler? We are the most affordable tour company for single travelers, and our policies and rates are the very best. Please see our single traveler policies.

Cancellations: If you cancel your tour reservation, your cancellation fee will be determined as follows:

  • If you cancel 90 or more days prior to the start of your tour, there is no cancellation fee.
  • If you cancel between 0 and 89 days prior to the start of your tour, all tour payments will be forfeited.


Sunday and Monday Nights: Sun, sea and unmatched casual luxury. Play under tropical skies beside a white sand beach. Stay in luxuriously appointed rooms, suites, bungalows or a private beach house, and dine in a uniquely different venue every night of the week!

Tuesday Night: Top-rated among resorts in Marathon, Tranquility Bay Beach House Resort is in the heart of the Florida Keys. Their amenity-rich, luxury Florida Keys resort provides unrivaled peace and seclusion alongside the sparkling waters of the Gulf of Mexico.

Wednesday and Thursday Nights: Having been the beneficiary of an award-winning renovation in 1999, the property is now home to a delightful small inn perfectly situated in the quiet heart of Old Town while being just an easy walk to all that makes Key West such a sought-after destination. The property is composed of several small buildings spread out on an acre of grounds, and includes a large heated pool and cabana surrounded by palm trees.

What’s Included

Professionally guided kayaking, sunset cruise, park entrance fees, wine and cheese reception, Conch Train ride, entry fees for Ernest Hemingway Home and Museum, Harry S. Truman Little White House, Key West Butterfly and Nature Conservatory, Dolphin Research Center, tennis courts, paddle boards, kayaks, fishing equipment, 5 nights accommodations, 4 dinners, 5 breakfasts, bicycle and helmet, free transfer from a hotel near Miami International Airport to Playa Largo and from Key Lime Inn to Key West Airport.


We are happy to provide you with a bike to use at no charge. Our bikes come equipped with a front handlebar bag, rear carrier, water bottle, mirror and flat pedals. Pedal cages and soft gel seat covers are available on request. We are also happy to put your own clipless pedals (pedals that attach to your biking shoes) and seat on your bike if you wish. Specific details and styles of bikes available in each location are indicated under each photograph below. The make of bikes provided varies by location. E-bikes will be available in the Florida Keys starting January 2019.

Virtual Tour of the Florida Keys

Biking and Weather

Biking. While biking is a part of this tour, it is only one element of the total experience. Our biking mostly parallels the Overseas Highway which follows the route of the old Henry Flagler Railway. This road connects all the keys and is a decidedly busy (mostly) two-lane road.  We avoid biking on this road by using the “Old State Road” and the beautiful paved Florida Keys Overseas Heritage Trail, which now covers 70% of the entire island chain. We have also built into the design of this tour the use of our passenger van so as to assure you will avoid any sections we consider inappropriate. The daily biking mileage is indicated at the end of each day in the itinerary.

Weather.  Due to the proximity of the Florida Keys to the Gulf Stream and the Gulf of Mexico, they enjoy a mild tropical-maritime climate and are one of the most reliably sunny and warm places in the United States year round. In the winter months, the sky is blue, showers rare, and  temperatures range around 75-80 degrees with warmer days mixed in. In fact, even Floridians come to the Keys in the winter so as to get away from the sometimes unreliable and chilly winter weather they experience elsewhere in their state.