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Road cycling routes
United States
Monroe County

Islamorada

The best road cycling routes around Islamorada

5.0

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148

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Road cycling routes around Islamorada are characterized by flat terrain and coastal paths, offering views of the aquamarine waters of the Florida Keys. The region features dedicated cycling infrastructure, including sections of the Florida Keys Overseas Heritage Trail, which utilizes historic bridges. While generally flat, some routes include short, noticeable elevations over bridges. This environment provides a unique setting for road cycling, combining natural beauty with accessible routes.

Best road cycling routes in Islamorada

  • The most popular road cycling route…

Last updated: May 17, 2026

20

riders

#1.

The Oceanview Inn & Sports Pub – Islamorada loop from Tavernier

38.2km

01:50

40m

40m

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

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Easy

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. 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

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

Moderate

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Popular around Islamorada

Florida Keys Overseas Heritage Trail — A walk in paradise

Running Trails around Islamorada

Other adventures around Islamorada

Florida Keys Overseas Heritage Trail — A walk in paradise

Hiking Collection by

Sue

Tips from the Community

Bear S.
October 31, 2025, Windley Key Fossil Reef Geological State Park

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

Translated by Google

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

Free parking and toilets available.

Translated by Google

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Sue
April 5, 2025, Conch Key

Conch Key is a small community in the middle of the Florida Keys, covering approximately 5 acres. This area had only a few residents until around 1952, when the Coral Shores School opened—the first public school outside of Key West, creating a population boom. Conch Key features several motels and vacation rental spots, as well as a fantastic seafood restaurant with beautiful views from its dock area.

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Sue
April 5, 2025, Anne's Beach Park

Anne's Beach is a fantastic park and a popular destination for kiteboarders, especially for beginners. Even though the beach is oceanside, there is minimal wave action due to the large area of shallow water, characteristic of beaches in the Florida Keys. The beach features a designated shallow swimming area, picnic tables with covers, restrooms, and access to drinking water. There is also a lovely boardwalk that meanders through the mangroves. This spot is a perfect place to take a break for lunch while enjoying the stunning views of the Atlantic Ocean.

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Long Key State Park spans 965 acres, and is a beautiful location with a fascinating history. In the early 1900s, it was a luxurious getaway along Henry Flagler’s railroad to Key West, housing the Long Key Fishing Camp. This camp attracted many notable figures, including celebrities and well-known saltwater anglers like author Zane Grey and several U.S. presidents. Sadly, the facility was destroyed by the Labor Day Hurricane of 1935 and was never rebuilt. Today, Long Key State Park is a popular destination for a wide range of recreational activities, including kayaking, hiking, birdwatching, picnicking, flats fishing, and snorkeling. There are two fantastic hiking trails to explore, and visitors can rent kayaks from the ranger station to paddle along the scenic shoreline to get a closer look at the diverse wildlife in the mangroves in the clear, shallow waters. The park also offers oceanfront, hike-in, tent-only campsites that include a picnic table, grill, hammock stand, and restrooms with cold outdoor showers. The site fee per night is $22 by reservation only and can be made here: reserve.floridastateparks.org or by calling the reservation line at 1-800-326-6521.

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Sue
April 4, 2025, Islamorada

Islamorada is a small village comprised of five islands in the heart of the Florida Keys, with some areas just one mile wide and five feet above sea level. Known as the “Sportfishing Capital of the World,” it features many professional charter boats and excellent fishing opportunities. There are many parks, open spaces, and several village beaches with tropical-themed bars, for plenty of options to enjoy the fresh, local seafood the town is famous for. While you're here, be sure to explore the Morada Way Art and Cultural District for a taste of local culture.

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Small and quite cozy pub for a stopover. Water view - rear access. theocean-view.com.

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Windley Key Fossil Reef Geological State Park, a former quarry, offers a glimpse into the Florida Keys' history. Henry Flagler's Overseas Railroad, built in the early 1900s, relied on its limestone. Later, the quarry yielded polished “keystone,” a decorative limestone unique to this area until the 1960s. The Hurricane Monument in Islamorada, at Mile Marker 82, is constructed from keystone extracted here. The park features several short loop trails throughout the grounds, where you can view the exposed fossilized coral reefs and remnants of the original quarry equipment. There is a drinking fountain, restrooms, and a lovely bench, perfect for a place to take a break under a canopy of hammock trees. The park is open daily from 8 am until sundown, with a $2.50 entrance fee. The visitor center operates Thursday–Monday, 8 am to 5 pm.

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Frequently Asked Questions

What is the terrain like for road cycling in Islamorada?

Road cycling in Islamorada is characterized by generally flat terrain, making for an easier cycling experience. The routes often follow coastal paths, offering stunning views of the aquamarine waters. While mostly flat, you will encounter short, noticeable elevations over historic bridges, such as the Snake Creek Bridge, which add a slight challenge.

Are there options for longer road cycling routes in Islamorada?

Yes, Islamorada offers options for longer road cycling routes. A significant choice is the Florida Keys Overseas Heritage Trail, which is a 39.6-mile (63.7 km) multi-use path. This trail utilizes historic bridges and runs parallel to U.S. Highway 1, providing a substantial ride through the coastal environment.

Are there easy road cycling routes suitable for beginners or casual riders?

Absolutely. Islamorada has easy road cycling routes perfect for beginners or those looking for a more relaxed ride. The Old Overseas Highway loop from Islamorada is an easy 18.6-mile (30.0 km) path that offers a serene experience on quieter sections of the historic highway. Another easy option is The Oceanview Inn & Sports Pub – Islamorada loop from Plantation Key, which is 15.1 miles (24.3 km) long.

What scenic views or natural features can I expect on Islamorada's road cycling routes?

Islamorada's road cycling routes are renowned for their stunning coastal scenery. You can expect continuous views of the aquamarine waters of the Florida Keys, swaying palm trees, and vibrant coral reefs just offshore. Many paths run along the ocean or bay side, offering tropical paradise vistas. The Florida Keys Overseas Heritage Trail, in particular, provides immersive coastal views.

What landmarks or attractions can I explore along the road cycling routes?

Along Islamorada's road cycling routes, you can encounter several interesting landmarks and natural attractions. You might pass by sections of the historic Overseas Highway, which incorporates old railway bridges. Anne's Beach Park is a popular choice known for its shallow waters and scenic boardwalk, offering a family-friendly spot for relaxation. You can also explore areas near Windley Key Fossil Reef Geological State Park, which offers trails through fossilized coral reefs.

Where can I find parking for road cycling trails in Islamorada?

While specific parking areas for each trail may vary, Islamorada is generally bike-friendly. Many local parks and public access points along the Florida Keys Overseas Heritage Trail offer parking. For example, Anne's Beach Park, which is a popular spot, provides parking facilities. It's advisable to check specific route starting points for designated parking.

What is the best time of year for road cycling in Islamorada?

The best time for road cycling in Islamorada is typically during the cooler, drier months, from late fall through spring (roughly November to April). During this period, temperatures are more moderate, and humidity is lower, making for more comfortable rides. Summers can be very hot and humid, with a higher chance of rain and thunderstorms.

What should I consider regarding weather when road cycling in Islamorada?

When road cycling in Islamorada, be prepared for warm and humid conditions, especially outside of the cooler winter months. Always carry plenty of water to stay hydrated. Sun protection, including sunscreen, sunglasses, and a hat, is essential due to the strong Florida sun. Afternoon thunderstorms can occur, particularly in summer, so checking the forecast before heading out is recommended.

Are there any circular road cycling routes in Islamorada?

Yes, Islamorada offers several circular road cycling routes. The Old Overseas Highway loop from Islamorada is an 18.6-mile (30.0 km) easy loop. Another option is the Key Largo Marina – North Beach loop from Tavernier, a 26.6-mile (42.8 km) moderate route. Additionally, the Islamorada – Anne's Beach Park loop from Plantation Key offers a 32.5-mile (52.3 km) moderate ride.

Can I expect to see wildlife while road cycling in Islamorada?

Yes, Islamorada's unique coastal environment provides opportunities to observe various wildlife. While cycling, you might spot diverse bird species, especially near mangrove-fringed waters. The clear aquamarine waters often reveal marine life, and if you're lucky, you might even catch a glimpse of larger creatures from the bridges or coastal paths. The region is known for its rich biodiversity.

What do other road cyclists enjoy most about the routes in Islamorada?

The road cycling routes in Islamorada are highly rated by the komoot community, with an average score of 5.0 stars. Cyclists frequently praise the stunning coastal views, the dedicated cycling infrastructure, and the generally flat terrain that makes for an enjoyable ride. The ability to explore historic bridges and access beautiful beaches like Anne's Beach Park is also a highlight for many.

How many road cycling routes are available in Islamorada?

There are over 4 road cycling routes available around Islamorada, catering to various skill levels. These routes range from easy loops to longer, moderate rides, all offering unique perspectives of the Florida Keys' coastal beauty.

Most popular routes around Islamorada

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