Biking the Florida Keys Overseas Heritage Trail: Best sections (2024)

Just as Henry Flagler longed to take his railroad to Key West, bicyclists have long dreamt of riding a safe bike trail to the southern tip of the scenic Florida Keys.

The dream is close to coming true, but we’re not quite there.

There is a bike trail operated by Florida State Parks, but it is not complete and it sustained hurricane damage from both Irma in 2017 and Ian in 2022.

PLEASE NOTE: As of April 2023, some bike bridges in the Lower Keys are still closed from Hurricane Ian damage, causing cyclists to revert to pedaling along the less safe and desirable roadside bike lane. The bridge over the Ohio-Missouri Channel at MM 39 is still closed and areas along Long Key State Park in the vicinity of MM 71 are bumpy and underwater after rain.

Despite the challenges, strong riders with street smarts and/or on guided rides bike the whole 106-mile-long Florida Keys Overseas Heritage Trail by the dozen every month, raving about the tropical scenery.

The bike trail through the Florida Keys may be flat, but it has its ups and downs. Many riders (me!) would not have fun on sections where you must ride on 3-foot-wide shoulders as cars whiz by at 50 miles per hour with drivers distracted by scenic beauty. If you read trip reports on Trailink, complaints about the bike trail are as common as is awe over the scenery.

On several visits to the Keys where my husband and I bicycled sections of the trail, I concluded there are sections that make the Florida Keys a great place to bicycle for nearly everyone. You just have to pick your spots. And when you do, you get to enjoy one of the key reasons I love to tour by bike: You take in the scenery at a slower pace, where it’s easy to stop and enjoy.

Here are recommendations for bicyclists who want to experience the Keys on their bikes but don’t want to bike the entire length or ride onnarrow shoulders adjacent to traffic.

I’ve assembled tips based on my experiences biking and driving the Overseas Highway, information from Florida State Parks and advice from Mark Terrill, biking guru at Key Largo Bike and Adventure Tours.

Some sections are more scenic than others. Some are safer and more comfortable than others. And it’s important to note that the entire trail is actually hard to follow, as it regularly crosses from bayside to oceanside and back, or continues on a parallel route not clearly marked and not visible from the U.S. 1.

For those who want to bicycle the entire length, Mark Terrill’s Key Largo Bike and Adventure Tours offers one- or two-day tours and a variety of other support services. He also offers bike rentals for longer or shorter rides and tours along specific sections of the trail. He has seen use of the path grow dramatically in recent years.

For shorter trips, riders can easily plan do-it-yourself tours, as I did.

Here are foursections of the Florida Keys Overseas Heritage Trail to consider for do-it-yourself Keys bike tours:

Islamorada

Between MM 90 and 80 along the Old Road

For 10 miles, the old state road (State Highway 4A) parallels U.S. 1 on the ocean side. It’s a scenic stretch, but has only occasional water views as it mostly passes through a woodsy residential area.

The homes range from multi-million-dollar gated mansions owned by celebrities (Coach Jimmy Johnson, actor Gene Hackman) to funky oceanfront trailer courts to resorts and businesses. It’s fun to spend time seeing life in the Keys up close, including places where people live and work.

The bike trail here is actually just a low-traffic residential road and is not clearly marked. (To make it more confusing, there is also a bike lane bayside along U.S. 1 too.)

At two short bridges in this section, the old road rejoins U.S. 1 and bicyclists cross the bridge in a designated lane along the shoulder. While I wouldn’t tackle the long Keys bridges riding in the shoulder (such as the Seven Mile Bridge), these bridges were easy and felt safe. We walked our bikes at the center of the bridges just to enjoy the view.

It’s easy enough to find parking in this area. We started from The Islander Resort, where we were staying, but there are spaces in the nearby Islamorada commercial district at MM 81.5 .

From there we pedaled south, turned around at the Tea Table Channel , then headed north and turned around at Coral Shores High School. Another good place to start your trek might be from that high school area.

On our 20 mile round-trip on this section of the Keys bike trail, we also enjoyed stopping at picturesque marinas like Bud N Mary’s (MM 79.8) and historic sites, including the interesting hurricane memorial at MM 81.5.

The hurricane monument tells the story of the devastating 1935 storm. In 1937, ashes of many of those who died were buried here when the monument was dedicated. Be sure to see the beautiful tile-mosaic map of the islands hit by the storm in front of the monument.

There’s a charming small residential area between the hurricane monument and ocean in Islamorada and it’s worth exploring on bike to the end, where you’ll find the Moorings, the expensive resort popular for fashion shoots. It’s also where the Netflix series Bloodlines is filmed.

We also shopped at the Old Road Gallery (88.8 on U.S. 1 and with an entrance also on the old road), which has gardens and an adjoining “Red Cross hurricane house” now used as an art gallery, which you can tour.

Islamorada cherishes the historic extra-strong poured concrete houses built by the Red Cross to house survivors of that 1935 Labor Day hurricane. You’ll pass several marked withplaques on the ride.

Around the Old Road Gallery we also admired some of the dozens of peaco*cks that roam this area.

You’ll have an easy time finding a place to pause for a snack. Here are a few suggestions: Midway Café and Coffee Bar, MM 80.4, which earns 4.5 stars on both Yelp and TripAdvisor; Lazy Days Restaurant, MM 79.8 oceanside, has excellent fresh fish and a spectacular ocean view.

Located along the way are two craft breweries in Islamorada that are worthwhile places to end your ride. Here’s more about them.

Here’s a Florida Rambler story about how Islamorada is emerging as a hub for activities.

Long Key section

Between MM 71 at the Channel 5 Bridge to the end of the historic Long Key Bridge at MM 62

This 18-mile-round-trip section of the Florida Keys Overseas Heritage Trail has spectacular views of water and sky, including from the 2.2-mile-long historic Long Key Bridge.

Because it is close to the water oceanside, this section was badly damaged by waves and flooding from Hurricane Irma in 2017. During 2020, however, most of this section has been repaired.

For this ride, you can park at the southern base of the Channel 5 Bridge at MM 71 bayside at a lot for those using the fishing bridge. (One drawback: You almost immediately have to cross the highway as the trail continues on the ocean side.)

On this route, you’ll also cross the shorter Tom’s Harbor Channel Historic Bridge (MM 61), which, like the Long Key Bridge, has cantilevered fishing platforms added to provide space for both fishing and bikes.

The bike path runs along Long Key State Park, and has some good views of the beaches and the beguiling turquoise water. (It’s a beautiful park; it’s well worth making a stop here.)

The Long Key bridge is the second-longest bridge of Henry Flagler’s railroad and is preserved as a bike and pedestrian path parallel to the new highway bridge. Smooth and traffic-free, it is as scenic and safe as a bike trail can get. (My husband, who doesn’t like heights, did have to ride right down the middle to avoid freaking out.)

Once you cross Long Key Bridge, however, the improved trail pretty much ends and is just a 3-foot-lane along the shoulder for the next two miles south. Instead of continuing, we crossed to the bayside and rode through Little Conch Key, a funky island with old cottages, mobile homes, views of the water and lots of general Keys flavor. From there, we turned around at MM 62 and headed back.

If you want a short ride just on the Long Key Bridge and back, you can park at the southern end of the bridge at MM 65.6, where this is a parking lot and signage.

Lower Keys to Key West

From MM 15 to Key West and back

This may be the best section of the FKOHT. My husband and I rode MM15 to MM5 and back in December 2016.Here’s my full report.

What we liked:

• It’s carefree. For the entire stretch, the trail has its own lane, hugging the water on the ocean side, included its own dedicated bridges. (NOTE: Hurricane Ian in September 2022 knocked out some bridges and sections in the Lower Keys where bicyclists must use the bike lanes on US 1.)
• The scenery. Highlights are a half dozen bridges and longstretches with open views of water.
• There’s a great starting point where you can park and caffeinate– Baby’s Coffee at MM15 — and some good turn-around spots, like Key West Botanic Gardens on Stock Island in Key West.
• Here are the details on the bike trail intoKey West.

Old Seven Mile Bridge to Sombrero Beach

This tourwill be about 14 miles roundtrip, but with thescenery and activities, you could spend all day on it.

Start your ride near the start of the Old Seven Mile Bridge at MM 47 bayside. There’s a parking lot there, but it’s hard to find parking there because the newly re-opened bridge is so popular.

It’s a gorgeous 2.2 mile ride on the refurbished section of the Old Seven Mile Bridge, so 4.4 miles round trip. There are bike lanes here and views the whole way. Here’s more about biking and visiting the Old Seven Mile bridge.

For a longer ride from the bridge area, pedal north along the Oversease Keys Overseas Heritage Trail for three miles through Marathon. At this point, the trail is separate from the highway and is located bayside. At MM 50, Sombrero Beach Road, leave the Overseas Heritage Trail and ride a dedicated bike path east to Sombrero Beach. This is a beautiful free local beach and well-landscaped park with picnic tables, rest rooms, swimming and snorkeling. The nice thing about biking to Sombrero Beach is that you don’t have to worry about getting a parking space.

General tip for riding the Florida Keys Overseas Heritage Trail:

• On longer rides, flat tires are common because of road debris. Serious cyclists suggest Kevlar-lined tires, fat-tire bikes or at least plenty of spares. (We had two flat tires on one ride.)
• Take special care in crossing busy U.S. 1 and in residential and commercial areas where people are turning into or coming out of driveways. This is the most hazardous aspect of the trail.
• Prevailing winds make a south-bound trip easier than a north-bound one.
• The northern-most section of the trail – from MM 106.5 to 91 — is primarily a paved bike trail separated from the highway. But as nice as the trail quality is, it’s hard to recommend becauseit’s not terribly scenic.
• To pedal across the famous Seven Mile Bridge, you face a five-foot shoulder, often strewn with debris, as semis roar by and drivers gaze too long at the view. (Note: If you are on a bike and don’t want to ride across the Seven Mile Bridge, you can call a cab. In Marathon, they all have bike racks, Terrill said.)

Resources for planning a trip on the Florida Keys bike trail:

• Map of Florida Keys Overseas Heritage Trail
• Most recent trail brochure (PDF)
• State park website for Florida Keys Overseas Heritage Trail
• Electric bikes ARE allowed on the Florida Keys Overseas Trail.
• Mile marker guide with dozens of stops to help make the most of your drive south.
• Islamorada: New things to do make it an appealing stop
• Florida Keys wildlife: Places to see animals
• Tiki bars:Soak up the Keys atmosphere
• 12 great kayak outings in the Keys
• Best beaches in the Florida Keys