Florida Keys Tour

6-DAY / 5-NIGHT BIKE TOUR – $3,395
December 29, 2019-January 3, 2020 – $3,695

2020 Dates: January 26-31, February 2-7 (Sorry! Sold out) – $3,395

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 spectacularly 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 entire continental U.S.

This is a tropical paradise. You can enjoy the easiest of cycling, and immerse yourself in all the included pleasures of kayaking, paddle boarding, swimming, golf, tennis, and such other options as jet skiing, scuba diving, day sailing and deep-sea fishing. Equally important is the ample time you will have 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 of the most 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 the Dolphin Research Center, Robbie’s Marina (where you can feed the wild tarpon), and Windley Key. 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 Conservatory; visit Harry Truman’s “Little White House;” ride out to the huge red buoy that marks the southernmost point of the continental U.S.; and be 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 very 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 sites 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 |  | Islamorada: Cheeca Lodge and Spa

Today we take full advantage of our stay at our luxury destination resort. Discovery Bicycle Tours will provide you with transportation from Miami International Airport to Cheeca Lodge and Spa and get you there by early afternoon. Now relax and enjoy all of the amenities we include in your stay– go for an outing on Cheeca Lodge’s paddle boards or kayaks, enjoy tennis on their six courts, play a round of golf (clubs included), opt for their many excellent spa services, stroll out along their wooden fishing pier for a view of the bay, rest by the heated swimming pools or saltwater lagoon, or just lounge in the sun on the warm sands of their palm-tree-lined private beach. Later in the afternoon we will have a get-acquainted meeting followed by a superb dinner in one of their three restaurants.

MONDAY  | Islamorada: Cheeca Lodge and Spa

This is your vacation, so sleep in if you wish, or get up early to watch a sensational Florida Keys sunrise. After a leisurely breakfast, we will lead you on a ride to Robbie’s, 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. We enjoy a professionally guided kayak adventure (weather permitting) of the amazing mangrove “tunnels” to get an up-close and personal encounter with the flora and fauna of a mangrove ecosystem. For those wanting additional miles, we offer an optional 8-mile ride to an interesting fossil reef at Windley Key.

We arrive back at Cheeca Lodge in plenty of time to take advantage of the many exciting and fun experiences offered at the resort, or best of all, just relax by the ocean or by one of the heated swimming pools, and luxuriate in the warmth of south Florida.

Tonight we treat you to bay side dining at the Islamorada Fish Company, a local favorite featuring freshly caught seafood as well as a great selection of non-fish appetizers and entrees.

Biking: 8 or 16 miles. Easy

TUESDAY | Duck Key: Hawks Cay Resort

After another leisurely breakfast, we 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. Surely this must be one of the prettiest bike rides in the world. Today we include 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 the elegant Hawks Cay Resort on Duck Key. We arrive early enough to take full advantage of all this resort has to offer. Perhaps try your hand at kayaking, stand-up paddle boarding, or treat yourself again to some well-deserved relaxation by their private lagoon or indulge yourself at the Calm Waters Spa. Then, after a wonderful dinner, you can enjoy an evening refreshment sitting by their poolside tiki bar.

Biking: 26 miles: 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 Saloon.

Biking: 15 or 25 miles.

THURSDAY | Key West: Key Lime Inn

For early risers, morning can begin with a pre-breakfast “bike stroll” along the quiet streets of Key West for a chance to see the more renowned sites of town before the crowds descend. Afterwards, meet 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, we 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 Conservatory, 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, followed by a bountiful breakfast at the funky and fun Banana Café.  Afterwards, there is a guided visit to the Butterfly Conservatory 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.

reserveDecember 29, 2019-January 3, 2020 – $3,695
Reserve with $300 deposit 


January 26-31, 2020 – $3,395
Reserve with $500 deposit 


February 2-7, 2020 – $3,395 (Sorry! Sold out)
Reserve with $500 deposit

Final payment due 120 days prior to your tour (personal check, Visa, MasterCard, American Express or Discover)

Single Supplement Fee: $940*

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

  • If you cancel 120 or more days prior to the start of your tour, there is no cancellation fee.
  • If you cancel between 60 and 119 days prior to the start of your tour, you will forfeit 50% of all tour payments.
  • If you cancel between 0 and 59 days prior to the start of your tour, all tour payments will be forfeited.


Sunday and Monday Nights: The proffered glass of champagne as you check into Cheeca Lodge gives you a hint of what is to come. Here you can just kick back and relax, explore the resort’s 27 seaside acres with its gorgeous landscaping and lush gardens, the towering palms, and 1200 feet of beach frontage. Ready to play? You have unlimited use of fishing equipment (try your luck out on their 525 foot dock or hire a guide to take you farther out), or play the nine-hole, par three Jack Nicklaus designed golf course (they have clubs for you), or use the lighted tennis courts, their sea kayaks, sailboats or stand-up paddle boards. Long day of travel? Lounge in their shade cabanas and beach chairs, swim in one of their two pools or salt water lagoon, or opt for the luxurious tranquility of a spa treatment in their 5700 square foot facility. Then, at the end of the day, enjoy fabulous dining that includes the option to enjoy the  local catch of the day.


Tuesday Night:  Tonight we stay at the luxurious Hawks Cay Resort on Duck Key. Once again you are not only pampered with the best of accommodations, but also have available to you all sorts of fun possibilities — want to try stand-up paddle boarding, or go for a kayak tour of the key, or maybe opt for a bit of jet skiing or kite boarding? This is also a perfect place to relax after your day of biking. You can lounge around their lagoon, have an afternoon beverage at their poolside tiki bar, and maybe swim out to their sundeck. Sore muscles? Get  revitalized at the award-winning Calm Waters Spa.  Dinner tonight  features local seafood, fresh pastas  and a great selection from a Mediterranean inspired menu.


Wednesday and Thursday Nights: Our home for the last two nights is the lovely historic Key Lime Inn. This former estate property was constructed in 1854 and is included in the National Historic Register. 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. Garden paths and tropical foliage separate the various buildings giving the property a very tranquil and spacious feel.


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, free use of golf course, tennis courts, paddle boards, kayaks, fishing equipment, 5 nights accommodations, 4 dinners, 5 breakfasts, bicycle and helmet, free transfer from Miami International Airport to Cheeca Lodge and from Key Lime Inn to Key West Airport.