Explore the best rated trails in Key West, FL, whether you're looking for an easy walking trail or a bike trail like the Florida Keys Overseas Heritage Trail and N/A . With more than 1 trails covering 106 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
Anyone, and I mean anyone, who leaves less than 5 stars for this trip is misguided. Granted we are from Orlando FL where we don’t bicycle much bc of the crazy traffic but decided to do Key Largo to Key West. It was AMAZING. Bike paths were fine and yes be careful going over the bridges but many have accessory bridges you can cross. We did it in a week and did tikis and mom n pop hotels and craft breweries. This has been one of our best trips ever. We even took the cat. It was a blast.
There are only small sections of this advertised trail that are dedicated and away from traffic. Shared lanes are tight and very dangerous. We were disappointed to find out that the dedicated bike bridge, at 7 mile bridge stops at pigeon key. There are some portions of pave bike trail throughout key Largo that are off the road and offer a little buffer. I would not recommend segments that are shared with car traffic. This is not a true, 106 mile trail.
Heading south from the cold a buddy and I did the 105 miles from Key Largo to Key West in February 2021 splitting the distance at a hotel on Marathon. As mentioned by others, portions had a lot of sidewalks, driveways and store commercial entrances so we had to ride very alert and defensive at all times. There were some long portions on paths and on less-travelled parallel roads where we could relax. Some bridges had dedicated bike lanes but most bridges had a fairly wide shoulder. We used very high lumen, effective white strobes front and rear to give us the best chance of drivers spotting us from a distance. My opinion is that an effective white strobe on the front is mandatory with all of the road crossings. Seven-mile bridge has a 8-10' shoulder so personally it really didn't feel that unsafe but that's a personal decision. We had a blast and hauled you-know-what, it's not for the inexperienced, unprepared or faint of heart. There is plenty of debris to avoid on the shoulder and between the two of us we had 3 flats over two days. We expected that so I suggest carrying two tubes per person and have the ability to change your own flats. We had two non-riding buddies driving our support vehicle and scoping out Tiki Bars for the evening. Due to traffic there is some level of danger involved so take every possible precaution and ride as defensive and safe as possible. We both have Varia radar taillights so we know when vehicles are approaching from behind, they're worth their weight in gold.
We view our Florida Keys ride as an epic experience and one more thing checked off our bucket list.
We rode some sections but avoided the parts of the trail that did not seem safe. Parts of the trail are littered. The trail surface in some parts is in bad shape. But... riding over the water was pretty awesome.
We are in our early 60's and have biked several trails in recent years. We chose the Heritage Trail (Key Largo to Key West) to bike with another couple of who had never biked long distance and point to point with gear. We thought this would be a good trail since it was relatively short in distance and flat. As has been stated in other reviews, parts of the trail were well-maintained, the scenery was beautiful and we had some of the best meals/drinks ever on vacation. HOWEVER, if Florida wants this to be a tourist attraction, much trail work needs to be done. Some sections were littered with trash and road gravel and several pedestrian/cyclist bridges were closed, necessitating crossing to the next key alongside cars and trucks. This trail gave new meaning to "switchbacks" and crossing US1 was often challenging--a few designated crosswalks/caution lights would have been nice (take notes from Sanibel). The most harrowing was south of Cudjoe Key where we shared the road for about 4 miles. There was very little signage in spots and the trail would just end. Our friends opted to take a shuttle across 7 mile bridge due to safety concerns which were valid. We observed speeders who "passed" other cars and came dangerously close to us. Generally most drivers were respectful of cyclists; there was just a lot of traffic. While parts of the trail were great, overall we would not recommend to a novice rider or a low risk taker. Riding sections that are cyclist friendly are recommended until Florida Parks can make significant improvements for a safe and enjoyable thru ride.
The views are great for those of us who don't live near water, but the trail is in need of major repairs. South of Marathon, most of the trail bridges have been closed so you will need to use the bike lane on the road.
What a great concept and if repaired I would like to ride it again.
If you’re up for an adventure and are comfortable enough riding with tractor trailers, speeding traffic, and trucks towing huge boat trailers, this is the ride for you. I did it in September 19-20, 2020 solo, starting at Dagney Johnson Key Largo Hammock Botanical State Park. My husband supported my ride and had a cooler full of water, Gatorade, and cold towels soaked in icy water. I rode it in two segments, stopping in Marathon for the night. Although day 2 was less mileage, the stretch from Sugarloaf to KW was a killer with no shade, and a confusing and disjointed trail. It was of course blinding sun and scorching heat—and even by my standards (I am from Florida and used to the heat). I made it and was no worse for wear. Just did it again this weekend. 5/28/22
Beautiful area and views. I live in the keys so I ride sections of the trail with the bike path and some small bridges. I do not fell safe riding on the road. Too many cars.
My husband and I rode from Marathon to Key West. IMO The trail is not scenic or safe. Most of the ride is next to the highway where you encounter road debris. Our biggest disappointment was not being able to bike across the seven mile bridge. Only 2 miles have been repaired. Skip this one.
A gorgeous 2 mile ride out to Pigeon Key where the entrance fee is $30 for the day. We didn’t go in. We went on Tuesday, February 8 at the peak of the tourist season. Plenty of parking and the all bike and walking bridge was not crowded. Weekends ends may be different. The refurbished bridge is an easy ride. saw at least a dozen Spotted rays swimming along with a few small sharks. If you are in the area, don’t miss this.
I only rode short distances on Key Largo where there were so very many commercial entrances and exits that I road into the parking lots to avoid cars. The mid keys of Grassy Key and Marathon were better. Some historic bridges have excellent separate hike/bike crossings while others are dangerously close to high speed car lanes. Only saw 2 or 3 long distance bikers, mostly short distance day bikers. Completing this trail is only for courageous bike trail die hard challengers.
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