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United States

Monroe County

The best cycling routes in Monroe County

4.4

(53)

814

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37

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Touring cycling in Monroe County offers routes across a unique island chain, characterized by flat coastal paths and ocean views. The terrain is generally level, making it accessible for various skill levels. Routes often connect small islands and feature bridges over clear waters, providing a distinct cycling experience.

Best touring cycling routes in Monroe County

  • The most popular touring cycling route is Key West Cycling Loop, a 12.1 miles (19.4 km) trail that takes 1 hour 8 minutes to…

Last updated: April 24, 2026

4.5

(20)

177

riders

#1.

Key West Cycling Loop

19.4km

01:08

10m

10m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

25

riders

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Popular around Monroe County

Cycling around Key West

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Florida Keys Overseas Heritage Trail — A walk in paradise

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Florida Keys Overseas Heritage Trail — A walk in paradise

Hiking Collection by

Sue

Tips from the Community

Kerstin
October 16, 2025, Southernmost Point

Spectacular sunrise!

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The Key West Shipwreck Treasure Museum houses a 20-meter-high observation tower offering views of the city and the ocean. The observation tower is part of the Key West Shipwreck Treasure Museum, which celebrates the city's maritime history. Visitors can learn about the dangers of shipwrecks and the salvage industry that once made Key West prosperous.

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

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a bridge to connect one key to another; direktly build in the Golf of Mexico without land surounded. What a view !

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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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Very beautiful church with a wooden ceiling and colorful windows. Well worth a visit.

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Frequently Asked Questions

How many touring cycling routes are available in Monroe County?

Monroe County offers a diverse selection of over 30 touring cycling routes. The majority of these, 29 to be exact, are rated as easy, making them accessible for various skill levels. There are also 3 moderate routes for those seeking a bit more challenge.

What is the typical terrain and elevation like for touring cycling in Monroe County?

Touring cycling in Monroe County is characterized by generally flat coastal paths and ocean views across a unique island chain. The routes often connect small islands and feature bridges over clear waters. Elevation gains are minimal, typically ranging from 10 to 20 meters over distances of 10 to 40 kilometers, making for a relaxed riding experience.

What do other cyclists say about touring cycling in Monroe County?

The touring cycling routes in Monroe County are highly rated by the komoot community, with an average score of 3.9 stars from over 50 reviews. Cyclists often praise the scenic coastal views, the unique experience of island hopping, and the generally flat, accessible terrain.

Are there touring cycling routes suitable for beginners or families in Monroe County?

Yes, Monroe County is very beginner and family-friendly for touring cyclists. Out of the over 30 routes available, 29 are rated as easy. Routes like the Key West Cycling Loop (12.1 miles) and the Smathers Beach – Key West Lighthouse loop from Stock Island (13.4 miles) are excellent choices for a relaxed ride exploring historic streets and coastal areas.

Are there any longer or more challenging touring cycling routes in Monroe County?

While most routes are easy, there are a few moderate options for those looking for a longer ride. The Bike loop from Wells Key is a moderate 25.3-mile (40.8 km) trail that takes about 2 hours and 16 minutes to complete, leading through coastal landscapes.

What natural features or landmarks can I see while cycling in Monroe County?

Many routes offer stunning ocean views and pass by significant natural and man-made landmarks. You can cycle past the iconic Southernmost Point Buoy, explore Fort Zachary Taylor State Park with its beautiful beach, or discover the Historic Kapok Tree on Whitehead Street. Further afield, the John Pennekamp Coral Reef State Park offers unique natural beauty.

Are there any historical or cultural attractions along the cycling routes?

Absolutely. Cycling in Monroe County, especially around Key West, allows you to explore rich history. You can pass by the Key West Lighthouse, visit The Ernest Hemingway Home and Museum, or cycle along the vibrant Duval Street. The Key West Shipwreck Museum is another notable stop for history enthusiasts.

Are the touring cycling routes in Monroe County typically circular?

Yes, many of the touring cycling routes in Monroe County are designed as loops, offering convenient circular journeys. Examples include the Southernmost Point Buoy – Key West Lighthouse loop from Key West and the Fort Zachary Taylor State Park – Oldest house in Key West ca. 1829 loop from Key West.

What are the best times of year to go touring cycling in Monroe County?

The best time for touring cycling in Monroe County is typically during the cooler, drier months from November to May. This avoids the peak heat and humidity of summer and the hurricane season, providing more comfortable riding conditions.

Can I find places to eat or stay along the touring cycling routes?

Given the routes often pass through populated areas like Key West and Marathon, you'll find numerous cafes, restaurants, and accommodation options. These areas are well-equipped to cater to visitors, allowing you to easily refuel and rest during or after your ride.

Is there an opportunity for wildlife spotting along the routes?

Cycling along the coastal paths and through state parks like Fort Zachary Taylor offers opportunities for wildlife spotting, particularly marine birds and various fish species in the clear waters. The unique ecosystem of the Florida Keys provides a chance to observe local flora and fauna.

Are there any routes that offer a unique historical perspective?

Yes, routes like the Key West Lighthouse – Smathers Beach loop from Key West not only offer scenic views but also pass by historical sites, allowing cyclists to immerse themselves in the rich history of the area while enjoying the ride.

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 Cycling routes throughout Monroe County below and find the perfect route in your destination.

Everglades National ParkFlorida Keys WildernessMarjory Stoneman Douglas WildernessStock IslandBig Coppitt KeyKey West National Wildlife RefugeKey WestGreat White Heron National Wildlife Refuge

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