United States · November 2024 - April 2025

Florida Keys 4-day Bike Tours

Ride the entire Florida Keys for 4-days on this Self-Guided Tour

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Overview

Trail: Florida Keys Overseas Heritage Trail - paved Mileage: 140 miles – 35-mile daily average Tour timing: November through May Escape the winter chill and treat yourself to a tropical cycling adventure on the Florida Keys Overseas Heritage Trail. Spanning over 140 miles of paved paths with breathtaking ocean views, this 4-days and 3-nights tour offers the perfect blend of sun, sand, and serenity. Starting in Key Largo, you'll pedal south through the stunning Florida Keys, where every turn brings you closer to the vibrant culture, pristine beaches, and the warm embrace of island life. You will have the chance to explore the unique charm of each Key, with stops at laid-back beaches and casual, local eateries where you can enjoy the flavors of the Keys. This tour offers the ideal balance of adventure and leisure, giving you the satisfaction of earning your rest as you unwind with your toes in the sand, watching the sun dip below the horizon in the Florida Keys. Whether you’re soaking in the sun or savoring the fresh seafood, this tour is the perfect way to wash away those winter blues and recharge your spirit in paradise. If you would like a longer time in the Keys, you can have additional days in your favorite locations at the beginning or end of your tour. Give us a call or email to have our tour specialists design your perfect vacation. What’s Included: Nightly Accommodations, Digital Mapping & Voice Navigation, Electronic Itinerary, Trail Themed T-shirt and Patch. Extras: Luggage Shuttle, Bike Rentals and Extra Accommodations

Schedule

4 day Tour Schedule

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Day 1 - Key Largo Loop - 40 miles

Start your adventure in Key Largo with a scenic loop ride exploring the northeastern part of the keys. This out-and-back route along Highway 509 offers the warm Florida air and many trees on the quiet road ride.

After your ride, return to Key Largo for a peaceful evening. You can unwind with a stroll along the beach or relax at a local venue, soaking in the Key Largo's laid-back charm.

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Day 2 - Key Largo to Long Key - 35 miles

Following breakfast, set out on a southbound ride along the Florida Keys Overseas Heritage Trail. Today’s route takes you through the Upper Keys, showcasing spectacular views of both the Atlantic Ocean and Gulf of Mexico.

Stop in Islamorada to explore unique features of the area, such as feeding tarpon at a local marina or enjoying the views from a waterfront spot. Spend the night in Long Key and stay on the water.


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Day 3 - Long Key to Big Pine Key - 34 miles

After breakfast, continue your ride southward towards Marathon and crossing the iconic Seven Mile Bridge. This part of the journey is renowned for its breathtaking views of the open ocean and is a standout feature of the tour.  Soon after the bridge you could see the Key Deer near the Big Pine Keys where you will spend the night again by the water.



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Day 4 - Big Pine Key to Key West - 31 miles

Begin your final day with a ride towards Key West, taking in the serene scenery of the Lower Keys along the way.  

The Lower Keys provides the chance to eat at unique bars for lunch boasting their seafood and cold drinks. Upon reaching Key West, take the time to discover the vibrant history and character of this island city. exploring its lively streets and enjoying the warm island atmosphere. Celebrate your ride with the chance to experience the distinctive charm and culture of this iconic destination. Visit Duval Street where you can find all kinds of entertainment, restaurants and bars to see Key West's "One Human Family".

Stay for additional days in Key West as your bike rental is good for 7 days. Contact our office to speak with our Tour Specialists to find the perfect place to stay in Key West.

Dates (other dates available)

November 2024
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1 queen room - 2 people

24 - 27 November 2024

FROM$895.00/pp

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2 Beds in room - 2 people

24 - 27 November 2024

FROM$995.00/pp

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1 queen room - 1 person

24 - 27 November 2024

FROM$1,345.00/pp

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Add Ons

Hotel Night before tour in Key Largo

FROM$350.00

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Hybrid Bike Rental - 7 days

7-day bike rental (3 days in Key West)

FROM$350.00

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Luggage Shuttle - price per bag

FROM$225.00

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Road Bike Rental - 7 days

7-day bike rental (3 days in Key West)

FROM$350.00

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Hotel Night after tour in Key West

FROM$400.00

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Shuttle from Key West to Key Largo - 1 or 2 people

Shuttle back to where you started - 2 people

FROM$300.00

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Shuttle from Key West to Key Largo - 3rd Person

Shuttle back to where you started - 3 or more (each)

FROM$150.00

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