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Bike touring routes & trails
United States
Monroe County
Key West

Key West Cycling Loop

Easy

3.2

(13)

37

riders

Key West Cycling Loop

01:08

19.4km

10m

Cycling

The Key West Cycling Loop offers a delightful spin around the island, immersing you in a blend of coastal beauty and historic charm. You'll glide along mostly paved paths, taking in panoramic ocean views, lush tropical gardens, and the unique historic architecture that defines Key West. Keep an eye out for the wetlands in the Florida Keys National Marine Sanctuary and the vibrant atmosphere around the Southernmost Point Buoy. It's an easy 12.1-mile (19.4 km) touring cycling route with only 47 feet (14 metres) of elevation gain, making it accessible for all skill levels and typically completed in just 1 hour and 8 minutes.

Planning your ride is straightforward, as Key West is a very bike-friendly city with marked routes and dedicated lanes. While there are no specific permits or fees required for this loop, consider starting your journey in the early morning or late afternoon to enjoy cooler temperatures and potentially less crowded paths. Bike rentals are readily available across the island, making it easy to jump on and explore without needing to bring your own.

This loop is an excellent way to experience the essence of Key West, showcasing its vibrant culture and natural beauty within a compact ride. It's particularly notable for its accessibility and the opportunity to see numerous iconic landmarks and historic sites, including beaches like Smathers Beach. The route also connects to the broader Florida Keys Overseas Heritage Trail, offering a taste of the extensive cycling opportunities in the Keys.

Last updated: June 9, 2026

Tips

Cycling is not permitted along parts of this route

After 2.12 km for 145 m

After 2.34 km for 119 m

After 16.3 km for 65 m

Waypoints

A

Start point

Parking

Get Directions

1

2.19 km

Southernmost Point Buoy

Highlight • Monument

The Southernmost Point is considered the southernmost point in the continental United States and is located on the last of the Florida Keys, Key West. It is located on the edge of the city of Key West in the Upper Duval district on the corner of Whitehead Street and South Street. It's only a few minutes walk to the city center.

In fact, Southernmost Point is not the southernmost point of Key West. This is located on the US Navy base next door. Because Key West is an island, the southernmost point of the continental USA is near Flamingo in the Everglades.

In October 2017, the large painted buoy that marks the southernmost point of the continental United States was restored for the final time. Before that, the buoy, which is one of the most photographed subjects in the Florida Keys, was somewhat affected by Hurricane Irma. Local artist Danny Acosta was responsible for the new painting with the help of a few other people.

On January 1, 2022, the buoy was set on fire by two men. The two vandals had placed a Christmas tree directly in front of the buoy and set it on fire, which caused it to fall onto the buoy and damage it.

Translated by Google •

Tip by

2

2.60 km

Halloween 👻🎃

Highlight • Other

3

2.76 km

Historic House in Key West

Highlight • Historical Site

4

4.54 km

swamp on the keys

Translated by Google •

Tip by

5

4.76 km

Southernmost Hockey Club

Highlight • Rest Area

6

5.74 km

Smathers Beach

Highlight • 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.

Tip by

7

6.01 km

Key West Beach

Highlight • Beach

8

7.18 km

East Martello Museum

Highlight • Historical Site

This museum exhibits local history and art. The building is the best preserved Martello tower in the country.

Tip by

9

7.31 km

Key West International Airport

Highlight • Rest Area

This airport (ICAO: KEYW, IATA: EYW) is the southernmost airport of continental USA.

Tip by

9.98 km

Beach

Beach

11

19.1 km

Southernmost Point

Highlight • Monument

Spectacular sunrise!

Translated by Google •

Tip by

B

19.4 km

End point

Parking

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Way Types & Surfaces

Way Types

11.8 km

3.18 km

2.67 km

927 m

439 m

367 m

Surfaces

9.36 km

9.21 km

766 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

Powered by Foreca

Today

Thursday 2 July

31°C

28°C

14 %

Additional weather tips

Max wind speed: 10.0 km/h

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Frequently Asked Questions

What is the terrain like on the Key West Cycling Loop?

The terrain on this loop is predominantly flat with minimal elevation gain, making it accessible for most cyclists. You'll mostly find well-paved surfaces, though some sections, particularly those shared with the broader Florida Keys Overseas Heritage Trail, might have areas where tree roots have slightly buckled the pavement. Expect a smooth ride across historic Flagler Railroad bridges repurposed for cycling.

Is the Key West Cycling Loop suitable for beginners or families?

Yes, the Key West Cycling Loop is generally considered easy and very suitable for beginners and families. Its flat topography and mostly paved surfaces make it manageable for a wide range of fitness levels. Key West is known for being extremely bike-friendly, making it a great choice for a relaxed family outing.

What scenic spots and landmarks can I see along the route?

The loop offers diverse and picturesque scenery. You'll experience tropical landscapes, panoramic ocean views, and historic architecture. Highlights include the iconic Southernmost Point Buoy, Smathers Beach, and the East Martello Museum. You'll also pass by other significant spots like the Southernmost Point and the Key West Beach, offering expansive views of the Atlantic Ocean.

Does the Key West Cycling Loop connect with other trails?

Yes, the route incorporates significant sections of the Florida Keys Overseas Heritage Trail (55% of the route). It also passes through parts of United Street (8%), Fleming Street (8%), Simonton Street (7%), and Caroline Street (5%), integrating various local pathways into a cohesive loop.

Where can I park to access the Key West Cycling Loop?

Key West offers various public parking options, including metered street parking and public garages, particularly around the downtown and historic areas. Since the loop covers much of the island, you can typically find parking near many access points. Consider starting near a public beach or park for easier access to parking.

What is the best time of year to cycle the Key West Cycling Loop?

The best time to cycle in Key West is generally during the cooler, drier months from November to May. During this period, the weather is more pleasant with lower humidity and less chance of rain, making for a more comfortable ride. Summer months can be very hot and humid, with a higher chance of afternoon thunderstorms.

Are there places to eat or drink along the Key West Cycling Loop?

Absolutely! As the loop takes you through Key West, you'll find numerous cafes, restaurants, and pubs, especially in the historic Old Town area. Many establishments are bike-friendly, offering a perfect opportunity to refuel and enjoy local cuisine or a refreshing drink.

Is the Key West Cycling Loop dog-friendly?

While Key West is generally pet-friendly, specific rules for dogs on bike paths can vary. It's best to keep dogs on a leash and be mindful of other cyclists and pedestrians. Some parks or beaches along the route may have restrictions, so always check local signage.

Do I need any permits or pay entrance fees to cycle this route?

No, there are no specific permits or entrance fees required to cycle the Key West Cycling Loop itself. However, if you choose to visit certain attractions or state parks along the way, such as Fort Zachary Taylor Historic State Park, standard admission fees may apply.

What should I pack for cycling the Key West Cycling Loop?

Given Key West's tropical climate, it's advisable to pack light, breathable clothing, sunscreen, sunglasses, and a hat. Don't forget plenty of water to stay hydrated. A small backpack for essentials, a phone for navigation and photos, and a bike lock if you plan to stop and explore on foot are also recommended.

Are there any specific safety considerations for cycling this loop?

While Key West is bike-friendly, always be aware of your surroundings. Some sections might involve riding on narrow shoulders alongside traffic, especially if you venture onto parts of U.S. Highway 1. Be prepared for potential crosswinds, particularly when crossing bridges, and always wear a helmet for safety.

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