Find the top rated walking trails in Islamorada, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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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.
Quad skated the entire trail and it’s fine. There’s roots but as long as you can manage that it’s not too bad. There’s roots quality on the south end is not too great but it’s short. The north end is more scenic than the south end. The biggest pro was that it was never too crowded. Mainly runners and a few bikes. Pathway is narrow but manageable for skaters.
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.
Very disappointing. We came to ride but is incredibly dangerous. Many multi use bridges across the ocean are closed as they are not being maintained. Therefore bikers must bike on the overseas highway where shoulders are narrow. Several places the biker must actually cross the highway which is extremely busy and dangerous.
If you are training for a marathon, this is one of the best long run trails. It’s clearly split so there isn’t ever really any traffic, it’s shaded about 80-90% of the time, and the views are lovely. People actually say “hello” versus on the beach where I usually run, people look at you like you’re nuts. Parking at the north entrance is easy, 2 hours free from 8am to 10am. Downsides: There weren’t any restrooms or water fountains anywhere. If you are running anything over 6 miles, bring a hydration vest and make sure that you don’t have to use the bathroom
Nice straight trail by a canal . You can see ducks , birds and fish. It cross some roads but it cars respect the bike cross . Only 2 not great things :1- no close by parking ,2- No shade so come prepared
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.
Just finish the trail from Coral Gables Old Cutler to 114 Ave then the south Dade Trail for a total 28 Miles. The trail is still deteriorating and lots of intersections are under construction, closed or bad signal but was able to finish it without any real incident and very safe from traffic. Still goes through not the best parts of Miami but we are all aware this trail crosses several unpopular parts of the county. Will repeat it next year and hope it improves once the intersections are finished.
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