bicycle key largo key west tour guided self

Biking the Florida Keys – Looe Key to Key West

Key Largo to Key West bike tour: day 3

This is the third and final blog covering our three-day Florida Keys bike tour. Day one provides overall details of our bike tour, including detailed trip planning and outfitting with Key Largo Bike and Adventure Tours if you are interested in making the trek.

As a refresher, this was a ride to celebrate my 59th birthday. Most serious road bikers would do the 100-mile stretch in one day, maybe two. We opted for three days, preferring to sightsee, drink and dine our way down the Florida Keys.

Day three arrived and our sights locked on the final 28 miles to Key West – the southernmost point in the United States and a mere 90 miles from Cuba. One of the great things about Key Largo Bike is their luggage shuttle service. We dropped our bags at the Looe Key Dive Resort desk at checkout, knowing when we arrived in Key West, our bags would be there. The bike shop also provides tips on side trips, great places to eat/drink and lodging along the route. They can do as much or as little as you need, including riding the entire 100 miles with you.

Bike adventure tour florida keys
There is so much to see and do biking from Key Largo to Key West. Unless you are itching to do your century in a day, two or three days allows lots of side trips.

Dedicated bike trails provide a break from Highway 1

We picked up Highway 1 at mile marker 28. Look to right along this stretch and you are likely to see Fat Albert, a tethered hot air balloon the military uses to monitor boats and low flying aircraft (code for drug smugglers). When you see Blimp Road on Cujoe Key you’re near the base where Far Albert resides. I didn’t actually ride down to see how close you allowed. But I did look it up on Google Maps and you can clearly see the landing pads. Cool in a geeky way.

At mile marker 26 and 23, paths lead bikers off Highway 1 to a peaceful trail through the woods and along the bay. This gives you a break from traffic and road noise for a bit. The trails are easy to miss so keep a sharp eye.

When you reach the Sugarloaf community (mile marker 17), a flashing light and crosswalk allow bicyclists to easily cross Highway 1. The Overseas Heritage Trail crosses Highway 1 several times, but usually without the benefit of a flashing light or crosswalk to slow oncoming traffic. Crossing can be a challenge at times.

bicycle florida keys bridges
Old Highway 1 bridges are the exclusive domain of bikers and fishermen as you near Key West.

Bicycle Stock Island and Key West

From here on in to Key West, the ride is what I envision the entire 106 miles will be one day. There are nice bike paths and best of all, bicyclists don’t have to share bridges with cars, but use the old Highway 1 bridges which have been restored and are the private domain of cyclists and fishermen. Around mile marker 15 you’ll find Baby’s Coffee, a favorite for cyclists needing their caffeine fix.

Continuing south you will see military jets flying overhead on training missions as you pass the Naval Air Station. Have to admit I stopped there quite some time to marvel as jets twisted and turned in tight formations.

You know Key West is near when you enter Stock Island, the cheaper real estate, more industrial area of Key West. Stock Island houses the Key West Golf Course, which is right across the street from the jail and adjoins the landfill. Hmmmm. When land is limited, I guess you put facilities where you can. Note to golfers: behave yourself and try to avoid deep divots.

Bicycle Key West Hogfish Bar
Four hungry bikers about to seek food and beer at Hogfish Bar.

Bicycle to Mile Marker 0. Then have a beer to celebrate!

We arrived at Stock Island at lunchtime by design, and pedaled to Hogfish Bar and Grill, located on the docks amongst the fishing fleet. It used to be that tourists were rare and locals enjoyed the freshest season at decent prices. Well its fame couldn’t stay a secret so now the locals share their secret with plenty of tourists. Hogfish is a must-do every time we venture to Key West.

Bellies full, we’re 5 miles from the 0 mile marker. Highway 1 intersects Roosevelt Blvd., signaling the start of Key West. Turn left here and follow South Roosevelt Blvd. to the end. You’ll immediately know you’re landed in a different place. If you want quirky and bizarre, this is the place. There’s nothing like it I know of in the U.S. It keeps us coming back year after year.

Where Roosevelt ends, grab your phone and plug Green Parrot Bar in your GPS because there are a few short blocks and a few turns to go. Conveniently, Green Parrot Bar is one of my favorite places to grab a beer and listen to live music, and it sits almost at the legendary 0 mile marker.

Have your photo made. Enjoy a beer or three. You have arrived. We stayed a week in Key West, keeping our rental bikes for transportation. When it came time to fly home, we simply locked the bikes up in a safe location and Key Largo Bike picked them up and took them back to their Key Largo shop. Much as I enjoyed a 100-mile tailwind ride, the 100 miles from Key West back to Key Largo would be tough.

Want to read about the other legs of our three-day trip? Here are links to Day One and Day Two.


  • Kathleen dent
    Posted at 09:22h, 31 December Reply

    My husband and I enjoyed reading about your adventure! We are headed to key west for four days and may do the last leg of your trip. Your descriptions are entertaining and make the ride sound well worth it!

    • admin
      Posted at 09:56h, 31 December Reply

      So glad it was helpful. Let us know about your trip! You are gonna love it.

  • Mary Nevin
    Posted at 22:29h, 16 August Reply

    I really appreciate the information you provided. I am planning a ride in February 2023 with my husband. I will be riding an electric bike with a range of 60 miles, so I should be fine. We will ride from Miami to Key West, round trip. Can you respond to where you stayed in Key West, please?

    • admin
      Posted at 16:37h, 24 October Reply

      We stayed in a friend’s house on the trip we wrote about. Other times we have rented small houses. There are some hotels also… everything from small and funky to Hyatts and such.

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