Bicycling Naples to Key West – Part 1

Back in 2016 or so, someone told me about a bicycle ride that sounded amazing – “72 Hours to Key West.”  That event leaves from Fort Myers and rides to Key West over three days.  Even with some of my recent biking accomplishments, I was too scared anxious to try that big of a ride with a group.  So instead, my good friend Shelley Rutkin (Birding for Life) and I hatched a plan that would enable me to do a similar ride by myself with her support.  We had several discussions about possible routes and what was important to me with this ride.  This is what we came up with.

Goals (aka, What did I want to accomplish?)

When I looked at the “72 Hours” route, the first thing I liked was that this is an actual “thing” and motorists are somewhat familiar with seeing cyclists along this route.  But what else really mattered?  Obviously, riding the Overseas Highway (US 1) to Key West was non-negotiable, but how important was it for me to ride it in just 72 hours?  How important was it for me to ride from Fort Myers?  How important were the specific hotels and extra activities?

I decided that starting from Fort Myers was not important to me.  What WAS important to me was to ride US 41 across the state; hence, I chose to start my ride from Naples making the total distance about 250 miles.  This was going to be my big cycling event of the year (like Cycle Adirondacks last year), so I didn’t want to rush it.  I wanted to be sure that I had challenging days but that I also took time to enjoy the ride.  We planned four days for the ride with a fifth “buffer day” in case of weather, illness/injury, or rare birds to chase.  I also felt that this was a CYCLING activity, so staying at fancy resorts and other off-bike activities were not important.  Basing the ride from Florida City would save a ton of money compared to staying in the Keys, and it also meant that the buffer day could be taken any time during the week.


View of the swamp/marsh from one of the bridges on US 41.

The Plan

  • Day 1 – Simply find the beach in Naples and start riding east on US 41.  Ride as far as the Shark Valley Visitor Center and then drive to the hotel in Florida City.
  • Day 2 – Drive back to Shark Valley and then ride east on US 41.  Turn south on Krome Ave (Hwy 997) and head towards the hotel.
  • Day 3 – Start riding from the hotel.  Head south on Card Sound Road, take Hwy 905 to the Overseas Highway (US 1), and finally ride south through the Upper Keys.  Hopefully make it as far as Marathon.  Drive back to Florida City for the night.
  • Day 4 – Drive back to Marathon to start the final push to Key West with a late evening drive back to the hotel in Florida City.
  • Day 5 – “bonus” day.  Assuming neither weather nor injury nor rare birds kept me from making it to Key West in four days, a fifth day could be used to put some miles on the bike in the Everglades.
  • Take at least three pictures of my bike in front of funky stuff each day.  This would force me to slow down and enjoy the ride instead of worrying about my speed.  (It kinda worked.)
  • Ride the ROAD and stay off the sidewalks/bike trails as much as possible to avoid congestion and pedestrians.
  • Be extra-vigilant about safety.  Pack my brightest jerseys, neon arm sleeves, neon socks/gloves, neon helmet, a bright flashing headlight, and two VERY bright flashing rear lights.
  • Look for safe stopping places every 17-22 miles.
  • Buy food for most meals at grocery stores and eat dinners in the hotel – saving time and money while optimizing nutrition (no heavy, greasy restaurant meals).
  • Bring enough electrolytes and on-the-bike food for the week.  I am a “big, salty sweater” so I am hyper-vigilant about taking in sufficient water and electrolytes while riding.
  • Ride without any music, mostly to keep me aware of cars but also to allow me to be more present with the wildlife and nature experiences.
  • No mapping software would be needed for this 250-mile ride with only three expected turns.
  • Make sure I have the right tools and spare items, since there will be no mechanic on the route and no SAG repair vehicle to pick me up.  Keep a spare inner tube with me on the bike; other items in the car with Shelley.

The Ride

Day 1: Naples to Shark Valley

The ride started at Naples Beach on Sunday, February 16th, where I simply wandered through the neighborhoods until I came to US 41 and headed east.

P1270102 B.jpeg

Ready to start the adventure.

The forecast called for 10 MPH headwinds and temperatures reaching the mid 90s – unexpectedly warm for this time of year.  Shelley found a gas station 17.5 miles down the road near Collier-Seminole State Park for the first rest stop.  We planned to meet next at Big Cypress Bend, at mile 27.

From there, we planned to meet at the Big Cypress Oasis Visitor Center – about 54 miles into the ride.  This is where I went wrong.  I overestimated how well I was riding, and the temps were heating up (my Garmin recorded a high of 105º that day).  By mile 37 (just 10 miles from our last rest stop), I was already through one of my bottles of water.  I stopped at a bar, “Joanie’s Blue Crab Cafe,” to buy more water, but my enjoyment for the day was starting to wane as I hadn’t yet eaten lunch and was getting hot.  Also, I had forgotten sunscreen and was sunburnt on my face and legs.  I stopped at several bridges where I sat on the guardrails in the shade for a few minutes before continuing.  I also rode through a strong downpour and started repeating a mantra – thanking the rain for “cooling my body and washing away my stress.”

There are several interesting places along US 41, but my favorite is the smallest US Post Office in the United States (Ochope, FL).  My bike is almost as wide as the building!


You don’t actually walk IN, but rather just up to this door.

Shelley met me at the Big Cypress Oasis Visitor Center at mile 54 with sandwiches, water/electrolytes, and iced coffee.  I love a bit of caffeine in the middle of a ride!  I was feeling rough and told her I wanted my next rest stop to be only about 10 miles away – she found an abandoned driveway/turnaround for that one.  At that rest stop, my next goal was just another five miles (not for fear of running out of water but running out of energy).  Shelley found a parking area by one of the canal stations at mile 70.  At that point, I felt ok to make the final push to Shark Valley, just four more miles away.  I was happy to get off the bike and into the air-conditioned car for the hour drive to the hotel.

This was the section of the ride where I saw the most wildlife.  Most people imagine alligators everywhere in Southern Florida, but the only ‘gator I saw was a 7-8 footer, dead on the side of the road, being picked apart by vultures.  I saw lots of birds:  a Limpkin eating an apple snail early on and a Snail Kite flying near the side of the road, also in pursuit of snails.  Once I saw a Great Egret, Wood Stork, Snowy Egret, and Great Blue Heron all standing together!  Wish I had stopped to take that picture.  There were also several Belted Kingfishers along the wires, more Anhingas and Great Egrets than one could count, and even a single Roseate Spoonbill alongside one of the bridges.

Day 2: Shark Valley to Florida City


Shark Valley Visitor Center.

We drove back to Shark Valley to start the day.  While the easterly winds continued, the weather was cooler and I was feeling better, so our goal for my first break was to meet at a gas station on the corner of US 41 and Krome Ave at about mile 18.

Heading south on Krome Ave was wonderful.  Well maintained bicycle trails alongside the northern section of the road made for a less stressful ride and even some occasional shade (left picture).  Shelley give me a bonus stop at mile 30 at a nice gas station.  At mile 33, major construction on Krome Ave forced me to detour west to Roberts Road for four miles.  This was a beautiful country road with no shoulders but also VERY little traffic (right picture).  I’m thankful that we drove that section of the planned route the previous day to learn about the construction and plan this new detour.

I had a final rest stop at mile 38 in a dentist office parking lot before ending the day at the Mobil station on Krome at mile 41 instead of the hotel.  I would start back at the gas station the next morning to preserve the continuity of the ride.  This saved a couple of dicey road crossings.

(Part two can be found here)

Read Shelley’s story about this part of the trip in her blog post, Bikes & Birds: Florida Version (Part 1 of 2).

1 thought on “Bicycling Naples to Key West – Part 1

  1. Pingback: Bikes & Birds: Florida Version (Part 1 of 2) | Birding for Life

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