Florida Keys Adventure - Key West
Florida Keys Adventure - Key West Sailing
Florida Keys - Everglades
Florida Keys Adventure - Key West Kayaking
Woman snorkeling in the Florida Keys
Birsd Florida Key West Bike Tours
Florida Keys Adventure - Key West Backroads Leader
Cycling on Backroads Everglades to  Key West Multisport Tour
Backroads Everglades to Keywest Multisport Adventure Tour
Florida Keys Adventure - Key West Wildlife
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Florida Keys Multi-Adventure Tour

Winter Sunshine from Everglades National Park to Key West

Couples, Friends & Solos

5 days 4 nights

Activity Level: 1-2

Premiere Hotels

From: $4,649 pp dbl occ

($1,100 for sgl occ)

In the water. Over the water. Under it, around it. Paddle on it, pedal above it. Plunge into it, sharing the experience with kaleidoscopic fish and maybe even sea turtles. Watch the sun set over it from the southernmost point in the country. How do you enjoy the true keys to happiness? It's easy—just add water.

Florida Keys Multi-Adventure Tour map
Florida Keys Multi-Adventure Tour map


Start Miami / End Key West

Start/End locations may vary. Do not book flights until your trip details are confirmed.


  • Explore unique ecosystems and diverse flora and fauna in the Everglades, an international biosphere—there's no other place like it!
  • Bike over aquamarine waters on the Overseas Heritage Trail's historic bridges, taking in spectacular tropical scenery
  • Look for marine life above and below the water as you paddle under the lush mangrove canopy
  • Witness colorful characters at the nightly festival on Mallory Square—a classic Key West experience


Accommodations may vary based on departure date.
5 Days Premiere Hotels
Accommodations may vary based on departure.
Days 1-2

Leaving bustling Miami, head to the Shark Valley Visitor Center and into Everglades National Park, an incredibly diverse place poetically referred to as a "river of grass" | On a private airboat tour, venture through the fascinating swamp habitat and learn about its rare flora and fauna | Cycle on a car-free bike path through the park's wetlands—keep an eye out for herons, storks and sunbathing alligators | Kayak through mangroves, searching for wildlife above and below the water | Travel from the Everglades to Islamorada, the Village of Islands | Enjoy a relaxing afternoon or take advantage of our resort's amenities.

Poolside view of Cheeca Lodge & Spa.
Cheeca Lodge & Spa
| Premiere Hotel

Part of the Islamorada scene since 1946, this amenity-rich beachside resort is set on 27 lush acres. (pool, spa)

Days 3-5

Explore the unique mangrove ecosystems and calm blue-green waters of backcountry Key West on a stand-up paddleboard | Bike along the Overseas Heritage Trail, a scenic paved path just for cyclists and pedestrians | Sail in the Florida Keys National Marine Sanctuary, home to the world's third-largest coral reef | Discover colorful tropical fish in shallow-water snorkeling | Looking for the quintessential Key West experience? Join the revelers at the Sunset Festival, brimming with street performers and local artisans | Explore Key West, part of the Florida Keys archipelago and known for its pastel-colored conch-style houses, on a walking tour, learning about the city's rich architectural heritage and why everyone from Harry Truman to Ernest Hemingway couldn't escape its unique lure.

Key West - The Marker Hotel
The Marker Waterfront Resort
Key West
| Premiere Hotel

Ideally situated on two acres of waterfront land and designed with a barefoot tropical luxury aesthetic, the Marker is named for the mile markers that lead to the southernmost part of the United States. (pool)

The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy.

Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy in USD.

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Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.

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Activity Level: 1-2

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.

Daily Route Options

Day 1
Level 1 | 15 miles | minimal elevation gain
Everglades Airboat Tour (1 hour)
Day 2
Excursion (half day)
Day 3
Stand-Up Paddleboarding (1.5 hours)
Level 1 | 13 miles | minimal elevation gain
Day 4
Sailing & Snorkeling (half day)
Level 1 | 17 miles | minimal elevation gain
Level 2 | 34 miles | minimal elevation gain
Day 5
Key West Walking Tour (1.5 hours)

What's Included

Available Bike Options

The key to a stellar day's ride is a bike that's perfectly in tune with your cycling style… Backroads has you covered with the best bike fleet in the world! Please note that bike requests are subject to availability and prioritized based on the date they're submitted.

Click the arrow to see all bike options.

Backroads Performance Road Bike
Backroads Performance Road Bike
Performance Road Bike

Included in your trip price

This custom-designed titanium bike is lightweight and responsive, featuring Shimano Ultegra Di2 electronic shifting, 11-speed compact gearing, a premium Mavic Ksyrium Pro wheelset and a full carbon fork. 

Backroads Touring Bike
Backroads Touring Bike
Touring Bike

Included in your trip price

A proven classic, this custom-designed titanium bike is suited for a wide range of cyclists. It features a comfortable ergonomic seat and a long wheel base that add to the bike’s control and stability.

Backroads Electric-Assist Bike
Backroads Electric-Assist Bike
Electric-Assist Bike

Included in your trip price

Keep pace or zip ahead, pedaling with an electric boost. This bike provides plenty of power to flatten the hills and more than enough battery range to cover the distance.
Min. age to ride e-bike: 16+

Also Included

  • All breakfasts, 5 lunches, 3 dinners
  • Expertise and services of our experienced Trip Leaders
  • Snacks and beverages between meals
  • Additional guides and experts from the region on many trips
  • Van shuttles to support a variety of route options
  • Comprehensive Travel Planner with detailed pre-trip information
  • Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
  • All gratuities at hotels and restaurants
  • Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
  • On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
  • Trailercycles, carriers, and kid-sized helmets for Family Trips
  • Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
  • Park and other entry fees
  • Fares for trains, ferries and other modes of travel as listed in the Travel Planner
  • Select coach transfers
  • Baggage transfers and porterage

Straight talk

We want to make sure you're on the right trip and that you have the best experience possible. Every Backroads trip is unique and this one is no exception.

Easygoing Adventure

This is a Level 1–2 trip, meaning the activities are easygoing and designed to allow us to take it slow and soak up the beauty of the region. Each day we embark on an active adventure, but the amount of time spent in the saddle and on the trails is less than the typical Backroads trip. We've paired our core activities with ones that are suited to this destination, such as kayaking and snorkeling. The level of these activities, combined with plenty of downtime to relax and take advantage of the resorts and beaches, result in the ideal way to experience Key West.


Long shuttles on Days 1 and 3 (sometimes made longer with traffic) allow us to cover the highlights of this dynamic region.

Peak Season Crowds

The Keys have their share of crowds and traffic, especially over peak holiday and spring break months. While we always aim to get off the beaten path, during certain times of the year traffic delays and slow service are unavoidable. Not to worry—we've built plenty of time into this itinerary to account for the relaxed pace, which the locals playfully call "Keys Disease"!

Weather-Dependent Activities

Water activities in the Keys are weather-dependent. Snorkeling can be canceled in the winter months due to low visibility. In the case of inclement weather, alternative activities are available.

A Place Like No Other

The Florida Keys are a truly unique destination teeming with fascinating history, vibrant character and quirky culture. On this journey expect to see everything from pristine beaches, out-of-this-world sunsets and mangrove forests to cruise ships, tackle shops and t-shirt stands.

Ask a trip expert

Have a question and need expert advice? Our team of Trip Consultants is here to help! You can also visit our Help Center.

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