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.
Last updated: April 24, 2026
5.0
(1)
61
riders
116km
04:17
20m
20m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
50
riders
64.8km
02:31
30m
30m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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5.0
(1)
38
riders
105km
04:44
70m
70m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
13
riders
63.7km
03:17
30m
30m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
50
riders
58.4km
02:20
30m
30m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
46
riders
62.4km
02:35
30m
30m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
30
riders
49.5km
02:01
30m
30m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
20
riders
30.1km
01:22
40m
40m
Easy road ride. Great for any fitness level. 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.
5.0
(1)
13
riders
52.3km
02:29
40m
40m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Monroe County
Road Cycling Routes in Marjory Stoneman Douglas Wilderness
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Road Cycling Routes around Key West

Road Cycling Routes in Key West National Wildlife Refuge

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Road Cycling Routes in Florida Keys Wilderness

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


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