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United States
Monroe County

Florida Keys Wilderness

The best road cycling routes in Florida Keys Wilderness

4.8

(6)

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6

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Road cycling in Florida Keys Wilderness is characterized by its exceptionally flat terrain, rising only a few feet above sea level. The region offers extensive coastal scenery with panoramic views of the Gulf of Mexico and the Atlantic Ocean. A significant feature is the Florida Keys Overseas Heritage Trail, which incorporates historic bridges and provides long stretches of paved path over open water.

Best road cycling routes in Florida Keys Wilderness

  • The most popular road cycling route is Florida Keys…

Last updated: July 13, 2026

5.0

(1)

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#1.

Florida Keys Overseas Heritage Trail

64.8km

02:31

30m

30m

Embark on a road cycling adventure along the Florida Keys Overseas Heritage Trail, where you will pedal across historic bridges connecting mangrove-fringed islands. The route offers continuous views of the…

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Moderate

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

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Cycling in Florida Keys Wilderness

Tips from the Community

Stenio Melani
June 25, 2026, Smathers Beach

Smathers Beach is the largest public beach in Key West, Florida, famous for its long stretch of white sand, exceptionally calm waters, and the beautiful setting of tropical palm trees.

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A must-see in Key West.

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There's an admission charge, too. But Bobby's view is great.

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Is also a museum and can be visited for an entrance fee

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A starting or endpoint of the US 1

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Sue
April 8, 2025, Smathers Beach

Smathers Beach, named after George Smathers (1913-2007), a former U.S. Senator from Florida and a friend of President John F. Kennedy, is the largest public beach in Key West, stretching about half a mile along the Atlantic Ocean. It begins at mile marker zero and is beautifully lined with coconut trees. On September 2, 2013, long-distance swimmer Diana Nyad made history by arriving at Smathers Beach after swimming 110 miles from Havana, Cuba, becoming the first person to complete the journey without a shark cage.

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Boca Chica Key, meaning “small mouth” in Spanish, is home to the largest Naval Air Station (NAS Key West) in South Florida. Boca Chica is known for its beautiful beaches and mangrove forests; however, you may hear jets during training exercises as you hike across this section of the trail. Some say the jets can get so close you can see the pilots!

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This is a fantastic café that offers traditional coffee drinks, tea, and smoothies, alongside specialty bagels, croissant sandwiches, pastries, and chocolates. If you visit during lunchtime, Baby's Grill, the food truck on-site, is known for its cheesesteaks and grilled chicken sandwiches, along with red beans and rice. They also have bottled drinks, making this an ideal stop to grab snacks and drinks during your adventure.

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Frequently Asked Questions

How many road cycling routes are available in the Florida Keys Wilderness region?

There are over 5 road cycling routes documented in the Florida Keys Wilderness region on komoot, ranging from easy to moderate difficulty. These routes are highly rated by the komoot community, with an average score of 4.75 stars.

What is the best time of year for road biking in the Florida Keys?

The best time for road biking in the Florida Keys is generally during the cooler, drier months from late fall to spring (November to April). During this period, temperatures are more comfortable, and humidity is lower, making for a more enjoyable cycling experience. Summers can be very hot and humid, with a higher chance of rain.

Are there any family-friendly road cycling routes in the Florida Keys?

Yes, the flat topography of the Florida Keys makes many sections suitable for families. Routes like the Smathers Beach – Key West Lighthouse loop from Key West offer an easy 17.8-mile path with coastal views and landmarks, ideal for a family outing. The Florida Keys Overseas Heritage Trail also has numerous accessible, paved segments perfect for all ages.

Can I bring my dog on the road cycling trails in the Florida Keys?

While specific rules can vary by exact location, many parts of the Florida Keys Overseas Heritage Trail and other public paths are dog-friendly, provided dogs are kept on a leash. Always check local signage or park regulations for the specific section you plan to visit to ensure compliance.

What kind of wildlife can I expect to see while cycling in the Florida Keys?

The Florida Keys are rich in diverse wildlife. Cyclists often spot various bird species like brown pelicans and great white herons, especially along coastal sections. Around Big Pine Key, you might even encounter the endangered Key deer. The mangrove ecosystems are crucial habitats for marine life and birds, offering glimpses into this unique environment.

Are there any loop road cycling routes in the Florida Keys?

Yes, several loop routes are available. For example, the Smathers Beach – Key West Lighthouse loop from Key West is an easy 17.8-mile option, and the Boyd's Campground – Baby's Coffee Key West loop from Key West offers a moderate 30.1-mile ride through coastal areas.

What amenities and facilities are available along the road cycling routes?

Along the Florida Keys Overseas Heritage Trail and other routes, you'll find various amenities, especially in and around towns like Key West. These can include cafes, restaurants, and accommodation options. It's advisable to carry sufficient water and snacks, especially on longer stretches between populated areas. Parking is often available at trailheads and public access points.

What makes road cycling in the Florida Keys unique?

Road cycling in the Florida Keys is unique due to its exceptionally flat terrain and the constant panoramic views of the turquoise waters of the Gulf of Mexico and the Atlantic Ocean. The Florida Keys Overseas Heritage Trail, in particular, offers an unparalleled experience of cycling over historic bridges above open water, providing a distinct feeling of riding above the sea.

Are there any permits required for road biking on the Florida Keys Overseas Heritage Trail?

Generally, no specific permits are required for recreational road biking on the Florida Keys Overseas Heritage Trail. It is a public multi-use trail. However, always be mindful of any specific park rules or regulations if you enter designated state parks or wildlife refuges along the trail.

What are some easy road cycling routes for beginners in the Florida Keys?

For beginners, routes like the Roadbike loop from Key West, an easy 12.6-mile path, or the Boyd's Campground loop from Downtown, an 11-mile easy route, are excellent choices. The flat terrain throughout the Keys makes many sections of the Overseas Heritage Trail also very accessible for those new to road cycling.

What do other road cyclists enjoy most about road cycling in the Florida Keys Wilderness?

The area is highly rated by the komoot community, with an average score of 4.75 stars. Reviewers often praise the stunning coastal scenery, the unique experience of cycling over historic bridges, and the flat, accessible terrain that makes for enjoyable rides. The opportunity to witness diverse wildlife and the vibrant blue waters are frequently highlighted as memorable aspects.

Can I use public transport with my bike to access trails in the Florida Keys?

Public transport options in the Florida Keys, such as local bus services, may have limitations regarding carrying bicycles. It's best to check with specific transit providers in the area you plan to visit for their current bike policies and availability. Many cyclists opt to drive to trailheads or start points with their bikes.

Most popular routes in Florida Keys Wilderness

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