The best road cycling routes around Key West
4.9
(12)
235
riders
12
rides
Road cycling routes around Key West are characterized by flat topography and coastal landscapes, making the island an accessible destination for cyclists. The region features extensive biking infrastructure, including designated bike lanes and multi-use paths like the Florida Keys Overseas Heritage Trail. Key West's compact size and island setting provide numerous opportunities for exploring historic sites and ocean views by bike.
Best road cycling routes around Key West
- The most popular road cycling route is Florida Keys Overseas Heritage Trail, a 40.2 miles (64.8 km) trail that takes 2 hours 31 minutes to complete. This route offers tropical scenery, historic bridges, and panoramic ocean views.
- Another top favourite among local road cyclists is Southernmost Hockey Club – Historic House in Key West loop from Stock Island, an easy 16.0 miles (25.7 km) path. This route navigates through picturesque streets with historic homes and provides access to landmarks like Mallory Square.
- Local road cyclists also love the Boyd's Campground – Baby's Coffee Key West loop from Key West, a 30.1 miles (48.5 km) trail leading through coastal areas and beyond the immediate Key West urban core, often completed in about 1 hour 57 minutes.
- Road cycling around Key West is defined by coastal paths, historic districts, and flat terrain. The network offers options for various ability levels, from leisurely rides to longer excursions.
- The routes in Key West are highly rated by the komoot community with an average score of 4.8 stars from over 15 reviews. More than 320 road cyclists have used komoot to explore Key West's varied terrain.
Last updated: July 7, 2026
5.0
(1)
50
riders
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 clear turquoise waters, making for a truly immersive experience. This moderate road cycling journey covers 40.2 miles (64.8 km) with a gentle elevation gain of only 95 feet (29 metres), typically taking about 2 hours and 31 minutes to complete.
When planning your visit, be aware that while much of the trail is a dedicated multi-use path, some sections require you to share the road with vehicles. You might encounter narrow shoulders in these areas, particularly on parts of the Seven Mile Bridge, so stay alert. Strong winds can also be a factor, especially on exposed bridge sections, so check the forecast before you head out.
This trail provides a unique perspective on the Florida Keys, allowing you to observe marine life like sharks, manta rays, and turtles in the waters below the bridges. You will also pass significant landmarks, including Mile Marker 0 in Key West, which marks the southern end of U.S. Route 1. The route's design offers a blend of natural beauty and historical context, showcasing the engineering marvels that connect these islands.
5.0
(2)
52
riders
58.6km
02:21
30m
30m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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31
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
35
riders
29.1km
01:15
20m
20m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
15
riders
18.9km
00:52
10m
10m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Key West
Tips from the Community
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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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 Key West?
Key West offers a diverse selection of over 12 road cycling routes, catering to various skill levels and interests. You'll find options ranging from leisurely rides through historic districts to longer excursions along the coast.
What is the best time of year for road cycling in Key West?
Key West's pleasant tropical climate makes it suitable for road cycling year-round. However, the cooler, drier months from November to April are generally preferred, offering comfortable temperatures and less humidity for your rides.
Are there easy road cycling routes suitable for beginners or families in Key West?
Yes, Key West is ideal for beginners and families due to its flat topography and extensive biking infrastructure. There are 9 easy routes available. For example, the Southernmost Hockey Club – Historic House in Key West loop from Stock Island is an easy 16-mile path that takes you through picturesque streets with historic homes.
What kind of scenery can I expect on Key West road cycling routes?
Key West road cycling routes offer a mix of stunning coastal landscapes, historic architecture, and vibrant island life. You'll encounter panoramic ocean views, historic bridges, and picturesque streets lined with colorful homes. Routes often pass by beautiful beaches and natural preserves.
Are there any longer road cycling routes for more experienced riders?
For those seeking longer excursions, Key West offers several moderate routes. The Florida Keys Overseas Heritage Trail is a prominent option, spanning over 40 miles and providing tropical scenery and ocean views. Another moderate choice is the Boyd's Campground – Baby's Coffee Key West loop from Key West, which covers over 30 miles through coastal areas.
What attractions can I see along the road cycling routes in Key West?
Many routes weave through areas rich in attractions. You can cycle past landmarks like the Southernmost Point Buoy, the Key West Lighthouse, and The Ernest Hemingway Home and Museum. Other notable spots include Duval Street and the Historic Seaport.
Are there loop trails for road cycling in Key West?
Yes, many road cycling routes in Key West are designed as loops, allowing you to start and end at the same point. Examples include the Southernmost Hockey Club – Historic House in Key West loop from Stock Island and the Roadbike loop from Key West, which offers a 12.5-mile circuit.
What do other road cyclists say about cycling in Key West?
The road cycling routes in Key West are highly rated by the komoot community, with an average score of 4.8 stars from over 15 reviews. Cyclists often praise the flat terrain, stunning ocean views, and the ability to explore historic sites and beaches by bike.
Is parking available near the road cycling trailheads in Key West?
Parking availability varies across Key West. While some areas, especially near popular attractions, may have paid parking, many residential streets offer free parking. It's advisable to check specific starting points for the most convenient options, or consider using bike rentals available throughout the island.
Can I access road cycling routes using public transport in Key West?
Key West has a local bus system, Key West Transit, which can help you get around the island. While buses may not be ideal for transporting your own road bike, they can be useful for reaching general areas where bike rentals are available or for connecting to different parts of the island before or after your ride.
Are there cafes or places to stop for refreshments along the road cycling routes?
Key West is well-equipped with numerous cafes, restaurants, and shops, especially in the Old Town and along popular routes like Duval Street and the Atlantic Coast. You'll find plenty of opportunities to stop for refreshments, grab a bite, or simply enjoy the local atmosphere during your ride.
What are the typical trail conditions for road biking in Key West?
Key West's road cycling routes primarily consist of paved roads, designated bike lanes, and multi-use paths. The terrain is generally flat, making for smooth riding conditions. While most surfaces are well-maintained, it's always good to be aware of potential sand or debris near coastal sections.
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