Scenic views in the Florida Keys on the Discovery Bicycle Tour

Guests standing behind their bikes on the Florida Keys Discovery Bike Tour

Guests riding in Florida Keys on the Florida Keys multi adventure Discovery Bike Tour

Pool on Florida Keys Discovery Bike Tour

Dolphins at the Dolphins research center on the Florida Keys Discovery Bike Tour

Florida Keys beach front on the Florida Keys Discovery Bike Tour

Sunset sailing on the Florida Keys Discovery Bike Tour

Kayaking the mangroves on Florida Keys Discovery Bike Tour

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6-Day Florida Keys Multi-Adventure Bike & Explore Tour

This is more than a bike tour! You bask in the warmth of the Florida Keys, biking a string of beautiful islands along the Florida Keys Heritage Overseas Trail that takes you to exciting Key West, with plenty of history and nightlife. You enjoy easy cycling and have options for kayaking, fishing, golf, tennis and much more.

Start - End: Miami - Key West

Total trip: 6 days

Average group size: 12 people

Level: 1

from USD 5,399/pp including taxes and fees

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Cycle across the Florida Keys to Key West, pairing easy island riding with mangrove kayaking, waterfront resorts, and unforgettable sunsets.

Escape to the Florida Keys and discover a side of winter filled with sunshine, ocean breezes, and laid-back island living. On this multi-adventure Florida Keys bike tour, you'll follow the paved Florida Keys Overseas Heritage Trail, riding from island to island across a chain of tropical keys connected by bridges and causeways on your journey to vibrant Key West.

With the Atlantic Ocean on one side and the Gulf of Mexico on the other, the riding is easy, scenic, and wonderfully relaxed. Along the way, settle into island life as you stay in waterfront resorts, kayak through winding mangrove tunnels, paddle tropical waters, relax poolside, and soak up the warm hospitality and fresh coastal flavors that make the Keys such a beloved escape.

Beyond the riding, discover some of the region's most memorable attractions, including the Dolphin Research Center, the lively atmosphere of Robbie's Marina, where giant tarpon gather beneath the docks, and the fascinating fossilized coral formations of Windley Key. You'll also pedal through iconic destinations including Islamorada, Duck Key, and Marathon, experiencing the unique character of each island along the way.

Your adventure concludes in colorful Key West, where you'll explore Ernest Hemingway's historic home, visit the iconic Southernmost Point, wander the charming streets of Old Town, and step inside the Key West Butterfly & Nature Conservatory. To finish, board a sunset sail across Key West Harbor and watch the sky turn gold as another unforgettable day in the Florida Keys comes to an end.

Tour Highlights

Biking

Florida Keys Overseas Heritage Trail

Cycle the iconic Florida Keys Overseas Heritage Trail, riding across scenic bridges and causeways that connect a chain of tropical islands on the journey to Key West.

Biking

Island-to-Island Riding

Pedal through some of the Keys' most beloved destinations, including Islamorada, Duck Key, Marathon, and Key West, with turquoise waters stretching out on both sides of the road.

Kayaking

Mangrove Tunnels

Explore the Florida Keys' remarkable mangrove tunnels on a guided kayaking adventure, discovering hidden waterways, coastal wildlife, and unique island ecosystems.

Wildlife

Dolphin Research Center

Get up close to dolphins and sea lions while learning about marine mammal conservation at the renowned Dolphin Research Center.

Explore

Historic Key West

Experience the colorful charm of Key West as you visit Ernest Hemingway's Home, the Southernmost Point, and the lively streets of Old Town.

Cruise

Sunset Sail Key West Harbor

Celebrate your adventure with a memorable sunset sail across Key West Harbor, complete with spectacular ocean views and the island's famous golden-hour skies.

Nature

Butterfly & Nature Conservatory

Step into a lush tropical paradise filled with hundreds of free-flying butterflies and exotic birds at the Key West Butterfly & Nature Conservatory.

Natural History

Windley Key Fossil Reef

Discover the fascinating fossilized coral formations of Windley Key, offering a glimpse into the geological history that shaped the Florida Keys.

Food & Flavors

Florida Keys Cuisine

Enjoy fresh local seafood, waterfront dining, Key lime treats, and the relaxed island atmosphere that makes the Florida Keys a beloved tropical escape.

Day by Day on Tour

Day by day, you'll pedal south through a string of beautiful islands, with turquoise water on either side and Key West waiting at the end of the road, soaking up ocean breezes, island culture, and the easy, sun-drenched rhythm of the Florida Keys.

Explore the map below.

Day 1

Arrival Day

We'll transport you 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.
Accommodation: Cheeca Lodge and Spa, Islamorada
Meals: Lunch, Dinner

Day 2

Stunning Seafood and Views

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 is well known for the large schools of majestic silver king tarpon that cruise to their docks. 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 7-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.

Dinner is together at a nearby seafood restaurant.
Accommodation: Cheeca Lodge and Spa, Islamorada
Meals: Breakfast, Lunch, Dinner

Biking: 9.3 miles (15 kilometers)
Elevation Gain/Loss: 47 feet (14 meters) ascent, 47 feet (14 meters) descent
Terrain: Easier

Day 3

Many Keys: Conch, Long, Fiesta, Duck

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 Hawks Cay Resort on Duck Key. Enjoy a dip in their lovely pool, soak in the hot tub, snorkel in the lagoon, or just gaze into the blue ocean.

Then, after dinner on your own (options at the hotel include the tiki bar or a high-end restaurant), you can enjoy an evening refreshment sitting by their poolside bar.
Accommodation: Hawks Cay Resort, Duck Key
Meals: Breakfast

Biking: 26.3 miles (42.3 kilometers)
Elevation Gain/Loss: 154 feet (47 meters) ascent, 154 feet (47 meters) descent
Terrain: Easier

Day 4

Pigeon Key

Today we begin cycling from Duck Key. We then cycle from Key to Key admiring the sparkling blue waters along the way. Circle back to Marathon Key for lunch before a shuttle into Key West. At Key West you are 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 Silver Palms 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. 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’oeuvres 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.
Accommodation: Silver Palms Inn, Key West
Meals: Breakfast, Lunch

Biking: 19.7 miles (31.7 kilometers)
Elevation Gain/Loss: 73 feet (22 meters) ascent, 77 feet (23 meters) descent
Terrain: Easier

Day 5

Wandering Key West

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, you have the option for an out-and-back ride back along the Keys to Baby's Coffee, or explore Key West. Perhaps you will choose 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 can 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.
Accommodation: Silver Palms Inn, Key West
Meals: Dinner

Biking: 52.3 miles (84.2 kilometers)
Elevation Gain/Loss: 311 feet (95 meters) ascent, 311 feet (95 meters) descent

Day 6

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 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. Or if you left a car at the Pullman in Miami, there's an option for a 3.5-hour shuttle back to that hotel.
Accommodation: Not applicable
Meals: Breakfast

Biking: 8.2 miles (13.2 kilometers)
Elevation Gain/Loss: 24 feet (7 meters) ascent, 24 feet (7 meters) descent
Terrain: Easier

What's included

5 nights’ accommodation
4 breakfasts, 3 lunches, 3 dinners
You’re supported from start to finish by our highly experienced guides and leaders
Industry leading Guest-to-Guide ratio (averaging 6:1)
All activities outlined in the itinerary
Delicious snacks and non-alcoholic drinks to keep you fueled
All necessary equipment (well-maintained and safe) for activities
Branded t-shirt and bag
Gravel bikes with drop handlebars, Hybrid with flat-bar handlebars, or E-Bikes - equipped with a front handlebar bag or rear carrier, branded water bottle, mirror, and flat pedals
Ride with GPS for navigation along with the detailed maps and itineraries
Transportation in our air-conditioned vans - safe, clean, modern, and comfortable!
Your queries answered by our knowledgeable Customer Care Team - only a call, chat, or email away
You’re “trip ready” with our Customer Care Team’s calls prior to your trip
“My Account” - your own online space with everything required for your adventure

Frequently Asked Questions

We know you might have a few questions before you book. Our frequently asked questions cover everything you need to know to feel ready for the ride.

Where does the tour start?

On the first morning of the tour, please meet at the Pullman Hotel at Miami International Airport at 11am. You're welcome to book your pre-tour stay at this hotel or any other hotel in Miami, though you'll need to make your own way to the pick-up point by the designated time.

Where does the tour end?

Your tour ends with a drop-off at Key West Airport at 1pm in time for afternoon flights, or we can transfer you back to the Pullman Hotel at Miami International Airport, arriving around 6pm.

What flights do you recommend?

Arrival: We recommend arriving in Miami at least the day before your tour starts. Many guests arrive a day or two early to accommodate potential flight delays and explore the city before the tour begins.

Departure: If flying out on the last day, we recommend departing from Key West Airport after 4pm. Earlier flight times will require a separate transfer booked at your own expense.

Where can I park my car?

If you plan to drive to the tour’s pick-up location, please ensure you arrange parking for the duration of your tour. If the pick-up point is a hotel, we recommend contacting them directly to inquire about parking availability. Keep in mind some hotels do not permit non-guests to park on-site, so you may need to find alternative parking options.

What accommodations do we stay at on this tour?

You'll stay at a carefully curated mix of waterfront resorts and charming inns throughout the Florida Keys. Each property is selected for its welcoming atmosphere, quality, and stunning beachfront location — perfect for relaxing after a day of cycling and water activities. Expect comfortable rooms, beautiful ocean or pool views, complimentary amenities, and easy access to beaches and island adventures. From sought-after island resorts with tropical grounds to a boutique Old Town Key West inn, every accommodation reflects the warmth and laid-back spirit of the Keys.