Biking the Florida Keys by Wandering Rose Travels

Bicycling in the Florida Keys – Overseas Heritage Trail

Itinerary for biking the Florida Keys

  • We flew into Ft. Lauderdale, rented a car and drove to Key Largo
  • We spent the night prior to our ride in Key Largo
  • Early Day 1 we met our outfitter, got bikes, and made our way to Marathon
  • Day 2 we biked Marathon to Looe Key with a detour to No Name Pub
  • Day 3 we biked Looe Key to Key West with a stop on Stock Island
  • We spent the next week in Key West, using our bikes for transportation
  • We left bikes in Key West for outfitter to retrieve, rented a car and drove back to Ft. Lauderdale

I love the Florida Keys. I love to bike. So what better way to celebrate my 59th birthday than bicycling the Florida Keys from Key Largo to Key West. The 106-mile Florida Keys Overseas Heritage Trail (FKOHT) includes 70 miles of paved bike trail running along Highway 1. Where no bike trails exist, you ride the shoulder of Highway 1. No fear, most of the shoulder is three to five feet wide.

We opted for a three-day bike trip down the Keys with lots of side trips, so I sought out an outfitter for bike rental, local knowledge and a luggage shuttle. We hit the jackpot when we discovered Mark Terrill and Key Largo Bike and Adventure Tours. Mark launched this venture six years ago, after serving as a cop in Los Angeles and then on a money laundering task force in south Florida. He is a bad ass, as well as bike outfitter and guide!

Mark Terrell, Key Largo Bike and Adventure Tours, local-outfitter

An bicycle outfitter with knowledge of the Florida Keys

The shop offers guided trips, supported trips (we opted for daily luggage shuttle and transport of the bikes from Key West back to Key Largo upon completion) and rental only if you don’t need support. Mark bikes the Keys every week and is fantastic about quizzing your interests to offer things and do and places to see along the way.

Our adventure began with a stay at Ocean Pointe Suites at Key Largo. The condo community sits on 60 beautiful acres and includes a boating dock and bar/restaurant. We shared a two-bedroom condo with Mary and Woody, our companions for this cycling adventure and many others. We stayed here for scuba diving trips more than 15 years ago. The place has not changed … in a good way … there’s still all the charm we remembered and everything was spiffy and up-to-date. It’s on my list as a place to return and stay a month or more for lots of biking and boating. There’s great snorkeling, scuba diving, kayaking and paddleboarding just up the road at John Pennekamp Coral Reef State Park – the first undersea park in the United States.

The winds of change blow our way

Our plan was a two-night stay, venturing around Key Largo before striking out for our bike adventure on Sunday. A check of the weather changed that plan when we discovered a 25-30 mph headwind predicted for departure day. I called Mark and he arranged for us to get the bikes a day early. Since our place was already paid for Saturday night, I came up with a “great plan” to bike from Key West to Marathon. Leave the bikes are our hotel in Marathon. Catch a cab from the hotel to the Marathon airport, rent a car and drive back to Key Largo for the night. Sunday we would drive the rental car with luggage back to Marathon. I marveled at my “brilliance” and adaptability and off we went.

After leaving the bike shop, the first 10 miles of the Overseas Trail follow the old route of Highway 1. This was a great way to see residential Key Largo life. At mile marker 90 on the old highway you enter what the locals call Millionaires Row. Actors, high rolling business people and a former NFL coach live along the way. This is the place for celebrating sightings.

Cyclists pop back out to Highway 1 at The Rain Barrel Artisian Village. This is a fun and quirky place to meet local artists and pick up something unique for a souvenir or gift. Have your photo taken with Betty, the 30-foot high lobster that greets visitors at the entrance.

Keys bike tour, including a stop at the Moorings palm tree from Bloodline

Bloodline filming locations to see along the way

We are big fans of the Netflix series Bloodline, filmed in the Keys, primarily around Islamorada. Mark gave us Bloodline filming locations to check out along the way. Crews were filming season two during our trip, adding to the excitement. Leave Highway 1 at Hurricane Monument and cycle Beach Road to find The Moorings Village & Spa, location of the Bloodline fictional hotel and beautiful beach where the Rayburns’ lives and misadventures unfold for TV viewers. Resort guests appreciate their privacy so the staff is quick to shoo off show buffs on a Bloodline filming locations tour, but we did manage to grab a photo on the iconic palm tree and briefly see the Blue Charlotte House and grounds before being asked to pedal ourselves outta there. The palm is said to be one of the most photographed palm trees in the world. Sports Illustrated, Victoria’s Secret, Tommy Bahama, Gap and others have done shoots here.

A few short blocks away is Islamorada Fish Company, our lunch spot for the day. The restaurant includes a seafood market, so ask what is local and fresh that day. Seating is on a covered deck completely surrounded by water. They get busy so you may have to wait. No fear. World Wide Sportsman has a mega store next door, or you can walk the docks and imagine yourself living the dream on one of the boats there.

After lunch it’s a quick hop to the Green Turtle Inn, an iconic Keys restaurant since the late 1940s. And the spot where Meg confessed her affair to Marco in Bloodline season one. Next on the show tour is Robbie’s of Islamorada where many of the boat scenes were filmed. Robbie’s caters to anything you wish on the water – boating, fishing, snorkeling and more. But many make the stop just to see the 100 or so tarpon that hang around the docks and delight tourists with their feeding frenzy when offered baitfish.

Islamorada Fish Company in the Florida Keys

Booking it to Marathon

There are other sights, but it was time to crank out some distance. The next few miles are a series of small islands and long bridges that connect Long Key, Duck Key and our destination of Marathon. We rolled into Glunz Ocean Beach Hotel around 5 p.m. We met Lisette at the front desk and explained our plan to leave bikes at her place, cab to the airport, rent a car and drive back to Key Largo. She gave me a “bless your heart” look (code for “you dumb ass”) and explained that the car rental companies close early on the weekend and a cab ride to Key Largo would be $130 or more.

This is when I witnessed the first of several examples of the Glunz model for guest service and satisfaction. Lisette discovered a staffer who was getting off duty and asked them to drive us to Key Largo in the owner’s Cadillac for less than half the price of a cab. So on our way and riding in style, we got a great history of the Keys from our driver for the next hour and a half.

Click here to continue the ride! Day 2: Marathon to Looe Key