Florida Keys Family Multi-Adventure Tour - 20s & Beyond
Florida Keys Family Multi-Adventure Tour - 20s & Beyond | Backroads
Florida Keys Family Multi-Adventure Tour - 20s & Beyond
Florida Keys Family Multi-Adventure Tour - 20s & Beyond
Florida Keys Family Multi-Adventure Tour - 20s & Beyond
Florida Keys Family Multi-Adventure Tour - 20s & Beyond
Florida Keys Family Multi-Adventure Tour - 20s & Beyond | Backroads
Florida Keys Family Multi-Adventure Tour - 20s & Beyond | Backroads
Florida Keys Family Multi-Adventure Tour - 20s & Beyond
Florida Keys Family Multi-Adventure Tour - 20s & Beyond
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Florida Keys Family Multi-Adventure Tour - 20s & Beyond

Winter Sunshine from Everglades to Key West

How do you enjoy the true keys to happiness? We invite you to find it 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. Find it all here on our magical Florida family adventure.

THIS ITINERARY: 5 days, 4 nights


FROM: $3,799 - $3,899 pp dbl occ
($1,050 for sgl occ)

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


Start Miami / End Key West

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

  • Explore unique ecosystems 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
  • Encounter marine life above and below the water as you paddle under the lush mangrove canopy
  • Discover colorful characters at the nightly festival on Mallory Square—a classic Key West experience
The Backroads Experience
The Backroads Experience
Backroads Multi-Adventure Trips
Backroads Multi-Adventure Trips
Backroads Trip Leader
Meet Our Leaders
Accommodations may vary based on departure date.
5 Days Premiere Hotels
Accommodations may vary based on departure.
Days 1-2

From 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, journey through the fascinating swamp habitat and learn more about its rare flora and fauna | Bike on a car-free bike path through the park's wetlands—keep an eye out for herons, storks and sunbathing alligators! | Look for wading birds in the mangroves as we travel from the Everglades to Islamorada, the Village of Islands, and our home for the first two nights | ​Swim with colorful tropical fish in shallow-water snorkeling ​| Enjoy a relaxing afternoon or take advantage of the amenities at our resort.

Cheeca Lodge and 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

Kayaking with your family through mangroves, search for wildlife above and below the water | On a walking tour, explore Key West, part of the Florida Keys archipelago and known for its pastel-colored conch-style houses | With your guide, learn about the city's rich architectural heritage and why everyone from Harry Truman to Ernest Hemingway couldn't escape its unique lure | Cycle along the Overseas Heritage Trail, a scenic paved path just for cyclists and pedestrians | Sail at sunset in the Florida Keys National Marine Sanctuary, home to the world's third-largest coral reef | Discover unique mangrove ecosystems on a stand-up paddleboard | Join the revelers at the Sunset Festival, brimming with street performers and local artisans—a quintessential Key West experience.

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)

Dates & Prices

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.

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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
Snorkeling Excursion (half day)
Day 3
Excursion (half day)
Key West Walking Tour (1.5 hours)
Day 4
Level 1 | 17 miles | minimal elevation gain
Level 2 | 34 miles | minimal elevation gain
Sunset Sail (1.5 hours)
Day 5
Stand-Up Paddleboarding (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! Read on for your available bike options for this trip.

Backroads Performance Road Bike
Backroads Performance Road Bike
Performance Road Bike

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

A proven classic, our most popular 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
NEW! Electric-Assist Bike

Our newly redesigned titanium e-bike is a lightweight yet powerful machine unique in the world of e-bikes. It provides plenty of power to flatten the hills and more than enough battery range to cover the distance.

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.

Electric-Assist Bikes

Note that electric-assist bikes are not allowed in the Everglades on Day 1.

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 FAQ's.