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If you want to experience biking Key West, America’s southernmost point, we have you covered. We lay down five incredible routes on the island and put them all together into the best biking route around Key West. From seasoned cyclists to beginning bikers, you’ll love exploring America’s tropics by two wheels.

Whether you cycle around Key West or challenge the Overland Trail to Key Largo, we’ll give you the low-down on the best bike trails, complete with an interactive Key West Bike Map you can load on your phone. Didn’t bring your bike? No worries, we’ll hook you up with the best bike rentals and in Key West and bike tours around this iconic Florida Key. If, by the end of this article, we haven’t answered all your Key West biking questions, drop us a line, and we will find it for you.

Key West is a biking paradise because it’s only 4.2 square miles, easy to navigate, and you can always find bike parking. Low-speed limits and ample bike racks make the island exceptionally bike-friendly, whether you’re biking through scenic neighborhoods or hopping on the numerous trails lined with breathtaking views, you will love biking in Key West.

To get you going, we’ve created routes on MapMyRide that give you turn by turn directions, show you the elevation and even have KML and GPX bike routes to export. Just load the app on your phone, click into our route, and never miss a turn! The route are linked to the names in the trail table for you to use and enjoy.


Challenge by Choice
Intro picture for our guide to biking in Key West

Key West Bike Map

Below is our Key West Bike map. We’ve included five bike routes and plenty of points of interest along the way. We’ve also added the highest-rated Key West bike rental shops and bike tours around the island. If the map doesn’t load, just hit the refresh button on your browser 🙂 You should also be able to load this map on your phone to have it with you as you bike around (when you’re stopped, of course).

Key West Bike Routes

East Perimeter Trail7.4 milesLoop around the island with lots of trail riding
Whitehead Street Bikeway1.0 milesRide from Mallory Square to the Southernmost Point
Front St to Fort Zachary1.2 milesFollow Front Street past the Little Whitehouse to Fort Zachary Taylor
Higgs Beach Connector1.0 milesLinks the Southernmost Point to the Perimeter Route
Stock Island Loop5.1 milesCircle Stock Island on backroads and the Overseas Heritage Trail
Best Biking Route Around Key West10.5 milesOur best route around Key West

East Perimeter Trail Loop

The East Perimeter Route travels the quiet side of the island, mostly on dedicated bike trails. It’s 7-miles long and will take approximately one hour to complete if you don’t stop along the way. Of course, what’s the fun of that?

The route starts at the West Martello Tower, one of the old forts on the island used as gunnery practice and has since been turned into a botanical garden. This is a loop trail, so in actuality, you can start anywhere along the way. From West Martello, you continue down Atlantic Blvd until you hit Bertha St. at the Southernmost Hockey Club (roller hockey, but it counts). The route jogs right for a block until you reach Smathers Beach.

Smathers Beach is the best trail on Key West. You bike along the boardwalk for about a mile with fantastic ocean views until you reach Cow Key Channel. Along the way, you’ll pass Fort East Martello, home of the world’s most terrifying and haunted doll – Robert the Doll. As you travel along the channel, your view changes from ocean to mangroves and then a residential neighborhood.

Once you cross Highway one, the Poinciana Plaza and New Town retail districts of Key West is on your left, and a salt marsh in on your right. You continue alongside Roosevelt Blvd until you reach the Key West Historic District. There’s really no wrong way through the Historic District. For convenience’s sake, the route shows a connector along White St. to close the loop back at West Martello. Of course, keep reading and we’ll show you how to combine east island bike paths with the historic district rides to form the best biking route through Key West.

Key West bike trail on the bike ride around Key West by the Cow Key Channel

Whitehead Street Bikeway

The Whitehead Street Bikeway runs parallel to Duval St and is the best way to bike across Key West while seeing the major highlights in an action-packed 1-mile ride. I purposefully started this route at the Shipwreck Museum instead of Mallory Square. Mallory Square is a wonderful place for a sunset, but there’s too much foot traffic to enjoy riding, and the cobblestones of Wall Street in front of the Key West Aquarium makes cycling less fun as well.

Biking down Whitehead, you’ll pass US 1 -Mile Marker 0, the Hemingway House, and the Key West Lighthouse. Whitehead Street ends at The Southernmost Point of the Continental United States. If you’re an early riser, this would be the perfect time to snap a picture of the most photographed spot on Key West before the crowds shows up.

Southernmost point marker, the most photographed spot on Key West

Biking Front St. to Fort Zachary Taylor

Taking Front Street to Fort Zachary Taylor is an alternative to Whitehead Street that’s more chill and mellow. You can even combine the two routes to form a Historic District Loop. You could connect up with the Perimeter Route via Palm Avenue and a couple of jig-jogs if you wanted, but the money section of Front St starts at the Shipwreck Museum.

The Front Street Route passes through the Truman Annex, one of the romantic neighborhoods in Key West. You cycle by The Little White House, where Harry Truman spent his winters ends up at Fort Zachary Taylor State Park, one of the best places to snorkel in Key West. Along the way, you’ll see the Mel Fisher Maritime Museum, the USS Ingham Museum, and the Florida Keys Discovery Center.

Beach at Fort Zachary Taylor, one of the best places to go snorkeling in Key Wets

Higgs Beach Connector

The Higgs Beach Connector takes you from the Southernmost Point to Fort West Martello, where the Perimeter Route starts. It’s a zig-zaggy connector route with lots of twists and turns. Don’t worry if you miss a zag; you can catch the next one. If you zig too soon, you’ll simply dead-end into the ocean. The route is drawn up along South-Vernon-Wadell-Alberta-Seminole-Reynolds. If you don’t like all those turns, just take South to Reynolds, turn right and head to the ocean. It’s about a mile anyway you cut it.

Points of interest along the way are the Key West Butterfly and Nature ConservatoryBarefoot Billy’s (where we jetskied around Key West), and Higgs Beach. The Higgs Beach connector will not set your world on fire, but it does connect two great bike loops on Key West, the Perimeter Loop, and the Historic District Loop. 

Garden view from West Fort Martello on the Higgs Beach Bike Route

Stock Island Loop

The Stock Island Loop is a five-mile flowing, fun ride with perhaps the best view on all of all the Key West Bike routes at Boca Chica Pass. You start on the Florida Keys Overland Trail near where Highway 1 runs into Roosevelt Blvd. You quickly pedal across the Cow Key Channel and make a left turn on College Rd. College is a mellow road with a decent shoulder, but there’s also a sidewalk if you feel safer there. You loop around for about a mile before you return to Highway 1, passing the Key West Botanical Gardens along the way.

Once you return to Highway 1, you continue to bike the Overland Trail a tenth of a mile until you reach the Shell Station at Key Haven Road. There is a gap in the Overland Trail here. You can look across Key Haven Road and see the trail restarting. I couldn’t recommend biking against traffic, but you can walk your bike the short distance until the trail starts back up. Continue biking to Boca Chica Pass. There, the trail passes under Highway 1 up onto the bridge. Bike out onto the bridge and enjoy the view before returning. Between the bike trail and bike lanes, you’ll have smooth sailing back to the start at Roosevelt Avenue.

An aerial view of Boca Chica Pass, the highlight of the Stock Island Loop.

Biking from Key Largo to Key West

The Florida Keys Overseas Heritage Trail will soon link Key Largo to Key West. It’s a 107-mile one-way trip across 37 bridges with many of the crossing car-free. There are still many gaps in the trail, but soon this will be a destination bike tour for cyclists everywhere who want a multi day adventure biking the Keys.

One of the bridges you'll cross biking from Key Largo to Key West

Best Biking Route Around Key West (in our opinion)

Here’s the moment you’ve been waiting for. We introduced the bike routes through Key West. We told you about the dedicated, ocean view trails on the eastern side of Key West. We showed you how to navigate the one-way streets of the Historic District while seeing all the highlights and photo-ops. Now, we put all of this together into what we consider the best biking route around Key West.

The route starts on Front Street and goes down to Truman Waterfront Park. You snake through the historic neighborhoods  past Blue Haven to the Hemmingway House and Key West Lighthouse. Take the Whitehead Street Bikeway to the Southernmost Point and then the Higgs Beach Connector to the perimeter trails. Instead of closing the loop with Truman Street, take Palm Avenue back into the heart of the Historic District.

This is an 10.3 mile loop that combines the flow eastern trails with the beauty of the Historic District. If want more riding, it joins up with the Stock Island Loop to form a 16.4 mile ride through paradise. We built a route in MapMyRide that lays it all out for you. You can also download the app and route to your device and use it to navigate the entire loop.

Key West Bike Rentals

There are many shops for Key West Bike Rentals. Our map contains the locations and websites of  highest-rated Key West bike shops that are listed below.

Bike rentals in Key West will cost you about $10 – $20 / day depending on the bike you select and the length of your rental. Often times, lights, helmets, and locks are included. Be sure to call ahead for reservations and ask about rental pickup and delivery. You could do worse than renting a bike for the duration of your vacation in paradise.

  • We Cycle: 305-292-3336
  • The Bike Shop: 305-294-1073
  • Island Bicycles: 305-292-9707
  • Eaton Bikes: 305-294-8188
  • Fury Key West Bike Rentals: 888-976-0899
  • Island Safari Rentals: 305-414-8142
  • Pirate Scooter Rentals: 305-882-9558
You will see many wild roosters on a Key West bike tour

Key West Bike Tours

Key West Bike Tours take you through the history and beauty of Key West. It’s almost like the famous Conch Train, only much more active. The highest-rated Key West bike tours locations and websites are on our map and their phone numbers are listed below:

  • Key Lime Bike Tours: 305-340-7834
  • LLoyd’s Tropical Bike Tour: 305-428-2678
  • Southernmost Bike Tours: 305-428-2678

Wrapping up Biking in Key West

Key West is a tiny island where Highway 1 ends. Between the rich history and outstanding views, it’s hard to think of a better place to ride your bike or take a romantic Florida vacation. You can connect all of these rides into an approximately 15-mile day of riding. We brought our bikes, including Jenn’s women’s specific hybrid, but there are plenty of places to rent bikes on Key West. Another great way to cycle Key West is to ride where you want to go instead of driving and parking. You’ll save money (and stress), and see beautiful sites along the way. Who knows, you might even earn yourself an extra order of conch fritters or a bonus slice of key lime pie!

Remember to ride safely and read our bike disclaimer before you go

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