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Routes
Road cycling routes
United States
Monroe County

Florida Keys Overseas Heritage Trail

Routes
Road cycling routes
United States
Monroe County

Florida Keys Overseas Heritage Trail

Moderate

4.9

(1317)

16,230

riders

Florida Keys Overseas Heritage Trail

03:17

63.7km

30m

Road cycling

Cycle 39.6 miles of the Florida Keys Overseas Heritage Trail, enjoying ocean views and historic bridges from Long Key to Sombrero Beach.

Last updated: February 26, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Florida Keys National Marine Sanctuary

Waypoints

A

Start point

Parking

Get Directions

1

478 m

Long Key State Park

Highlight • Rest Area

Small state park with swimming facilities. Formerly a luxury resort, now you can pitch your tent after making a reservation: floridastateparks.org/parks-and-trails/long-key-state-park

Translated by Google •

Tip by

2

3.50 km

Florida Keys Overseas Heritage Trail

Highlight (Segment) • Cycleway

The Florida Keys Overseas Heritage Trail runs for 106 miles through the Florida Keys and crosses over 37 bridges. Along the way you'll pass by many State Parks, beaches, bars, restaurants, and marinas; and all of them will be beckoning you to stop and stay a while. On the right day this is one of the best places to ride in the world.

Tip by

3

28.6 km

Overseas Railway Construction Headquarters

Highlight • Historical Site

In the early 20th century Marathon was the center of shipping operations in the region. Ships from Havana and other Caribbean locations would dock near the railway to offload their goods to trains heading north. However, this would all come to end in 1935 when a large storm damaged the rail lines and the highway soon replaced the railroad.

Tip by

4

31.9 km

Sombrero Beach

Highlight • Beach

Sombrero Beach is a quintessential Florida Keys beach. Soft white sand, crystal clear water, and plenty of facilities for your day at the beach. If you're biking out here, plan to stay a while.

Tip by

B

63.7 km

End point

Parking

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Way Types & Surfaces

Way Types

42.6 km

7.55 km

7.36 km

6.28 km

Surfaces

32.4 km

27.1 km

4.21 km

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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

Friday 8 May

30°C

26°C

0 %

Additional weather tips

Max wind speed: 13.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the terrain like on the Florida Keys Overseas Heritage Trail?

The trail is predominantly paved and flat, tracing the route of Henry Flagler's historic Florida East Coast Railway. You'll cycle over 23 repurposed railroad bridges, offering a unique island-hopping experience. While much of it is off-road, some segments require sharing the road with vehicles, particularly where the trail is incomplete.

How difficult is cycling this trail?

It's generally considered easy due to its flat profile, making it accessible for many cyclists. However, the intense Florida heat and humidity, along with potential headwinds, can add to the challenge. Be aware that some sections merge with US 1, requiring you to contend with traffic on narrow shoulders.

What are the best times of year to cycle the Florida Keys Overseas Heritage Trail?

The best time to cycle is typically during the cooler, drier months from late fall to early spring (November to April). This avoids the intense heat, humidity, and hurricane season of summer, offering more comfortable riding conditions.

Are there any permits or entrance fees required to use the trail?

No, there are no general permits or entrance fees required to access the Florida Keys Overseas Heritage Trail itself. However, if you plan to visit specific state parks or attractions along the route, such as Long Key State Park, those may have their own entrance fees.

Is the Florida Keys Overseas Heritage Trail dog-friendly?

Yes, the trail is generally dog-friendly. Leashed dogs are typically allowed on the paved sections. However, always check specific regulations for any state parks or beaches you plan to visit along the way, as their rules may differ.

Where can I park to access the trail?

Parking is available at various access points and trailheads along the route. Many state parks and public areas adjacent to the trail offer parking facilities. For instance, you can find parking near Long Key State Park or Sombrero Beach, depending on which section you plan to ride.

What can I see along the route?

The trail offers spectacular views of turquoise waters and mangrove-fringed islands. You'll pass historical sites like the Overseas Railway Construction Headquarters, and can access beautiful spots like Sombrero Beach. The repurposed historic Flagler Railroad bridges are a highlight, providing unique viewpoints over the ocean.

Does the trail intersect other well-known paths?

Yes, the route also passes through sections of the East Coast Greenway (FL) and the Florida Keys Overseas Heritage Trail, which is the official name for the majority of the path.

How long does it take to cycle the entire Florida Keys Overseas Heritage Trail?

The full planned corridor is 106 miles. While a specific komoot tour covers about 63.7 km (around 3.3 hours) of it, cycling the entire 90+ miles of existing paved trail from Key Largo to Key West would typically take multiple days for most cyclists, allowing time to enjoy the scenery and local communities.

Are there any beginner-friendly sections of the trail?

Absolutely. The trail's flat profile makes most of it suitable for beginners. The longest continuous paved section, found in the Upper Keys between Key Largo (MM 106) and Islamorada (MM 72), is an excellent choice for those looking for a smooth, uninterrupted ride away from traffic.

What should I bring for a day of cycling on this trail?

Given the Florida climate, essential items include plenty of water, sunscreen, a hat, and sunglasses. A basic bike repair kit, snacks, and a fully charged phone are also recommended. Consider wearing moisture-wicking clothing to stay comfortable in the humidity.

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Florida Keys Overseas Heritage Trail

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