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Routes
Road cycling routes
United States

Monroe County

The best road cycling routes in Monroe County

4.9

(12)

595

riders

18

rides

Road cycling routes in Monroe County, Florida, are characterized by their coastal setting and generally flat terrain. The region offers extensive paths along the Florida Keys, providing views of the Atlantic Ocean and Gulf of Mexico. Cyclists can expect routes that traverse causeways and bridges connecting the islands, with minimal elevation changes. The landscape primarily consists of mangrove forests, tropical vegetation, and marine environments.

Best road cycling routes in Monroe County

  • The most popular road cycling route is Flamingo to…

Last updated: April 24, 2026

5.0

(1)

61

riders

#1.

Flamingo to Long Pine Key

116km

04:17

20m

20m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

5.0

(1)

50

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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5.0

(1)

38

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

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

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy 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

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Monroe County

Road Cycling Routes in Marjory Stoneman Douglas Wilderness

Road Cycling Routes in Everglades National Park

Road Cycling Routes in Great White Heron National Wildlife Refuge

Road Cycling Routes around Stock Island

Road Cycling Routes around Key West

Road Cycling Routes in Key West National Wildlife Refuge

Road Cycling Routes around Key Largo

Road Cycling Routes around Big Coppitt Key

Road Cycling Routes in Florida Keys Wilderness

Road Cycling Routes around Tavernier

Other adventures in Monroe County

Florida Keys Overseas Heritage Trail — A walk in paradise

Hiking Collection by

Sue

Tips from the Community

Franz Josef Klingen
February 3, 2026, Main Park Road

A central road from which you can explore the landscape and the sights.

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Visitor Center

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Bear S.
October 31, 2025, Sombrero Beach

One of the most beautiful beaches in the Florida Keys.

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A small historical place. It's also interesting that there's still forest to be seen there.

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A must-see in Key West.

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Bear S.
October 26, 2025, Anne's Beach Park

Free parking and toilets available.

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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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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes in Monroe County?

Road cycling routes in Monroe County, Florida, are predominantly flat, offering a coastal setting with extensive paths along the Florida Keys. You'll traverse causeways and bridges connecting the islands, enjoying views of the Atlantic Ocean and Gulf of Mexico. The landscape features mangrove forests, tropical vegetation, and marine environments, with minimal elevation changes.

How many road cycling routes are available in Monroe County?

There are over 20 road cycling routes documented in Monroe County, Florida, on komoot. These routes cater to various preferences, with 13 easy and 9 moderate options, ensuring a suitable ride for most cyclists.

Are there any easy or beginner-friendly road cycling routes in Monroe County?

Yes, Monroe County offers several easy routes perfect for beginners or those seeking a relaxed ride. One popular option is the Southernmost Hockey Club – Historic House in Key West loop from Stock Island, which is 16.0 miles (25.7 km) and takes about 1 hour 12 minutes, leading through Key West's historic areas.

What are some longer road cycling routes for more experienced riders?

For longer rides, consider the Flamingo to Long Pine Key route, which spans 71.8 miles (115.5 km) and typically takes around 4 hours 16 minutes. This route offers a long, flat journey through the unique Everglades ecosystem.

Are there scenic routes with coastal views in Monroe County?

Absolutely. Many routes in Monroe County offer stunning coastal views. A notable option is a section of the Florida Keys Overseas Heritage Trail, a 40.2-mile (64.8 km) path providing scenic vistas along the historic Overseas Highway.

What can I see along the road cycling routes in Monroe County?

While cycling, you can explore various attractions. In Key West, you might pass by the iconic Southernmost Point Buoy or the historic Key West Lighthouse. Further afield, you can visit Fort Zachary Taylor State Park or the renowned John Pennekamp Coral Reef State Park.

Are there any historical landmarks or points of interest along the routes?

Yes, particularly in Key West. Cyclists can explore areas near The Ernest Hemingway Home and Museum, the vibrant Duval Street, and the Key West Shipwreck Museum, offering a blend of history and culture.

What do other road cyclists enjoy most about road cycling in Monroe County?

The area is highly rated by the komoot community, with an average score of 4.9 stars from nearly 20 reviews. Cyclists frequently praise the unique experience of riding along coastal paths, over historic bridges, and through tropical vegetation, often highlighting the flat terrain and scenic ocean views.

Are there any circular road bike trails in Monroe County?

Yes, many routes in Monroe County are designed as loops. For instance, the Roadbike loop from Key West is an easy 20.2 km (12.6 miles) option that allows you to start and finish in the same location, ideal for exploring the Key West area.

Can I find routes that pass through Key Largo?

Yes, Key Largo offers several road cycling options. The Key Largo Marina – North Beach loop from Key Largo is a moderate 62.4 km (38.8 miles) route, and the Old Overseas Highway loop from Key Largo provides an easy 37.4 km (23.2 miles) ride, both starting and ending in Key Largo.

What is the best time of year for road biking in Monroe County?

Monroe County, Florida, generally offers pleasant cycling conditions year-round due to its tropical climate. However, the cooler, drier months from November to April are often preferred to avoid the higher humidity and heat of summer, as well as the hurricane season.

Are there any routes that explore the Everglades ecosystem?

Yes, the Flamingo to Long Pine Key route takes you through a significant portion of the Everglades ecosystem. This long, flat ride provides a unique opportunity to experience the distinct natural environment of the region.

Most popular routes in Monroe County

Hiking in Monroe County

Most popular attractions in Monroe County

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Didn’t find what you were looking for?

Check out more Road cycling routes throughout Monroe County below and find the perfect route in your destination.

IslamoradaKey LargoEverglades National ParkFlorida Keys WildernessTavernierMarjory Stoneman Douglas WildernessStock IslandBig Coppitt KeyKey West National Wildlife RefugeKey WestGreat White Heron National Wildlife Refuge

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