106 Reasons to Walk The Florida Keys

The Florida Keys and Key West.  Just saying the words washes the stress away.

My love affair with the Keys started October of 1996 when I was in the Navy.  I was flying in a two plane formation of A-6E Intruders from Puerto Rico to Virginia Beach, Virginia.  We had to stop in at NAS Key West for fuel.  It was Fantasy Fest and we couldn’t stay.  As we came in to land I could see almost the entire length of the Keys bathed in the light of an orange sunset with pink cotton ball clouds floating above.  I was hooked.  Fifteen years later I started my bikini company, Conch Republic Bikinis in Key West.  I’m still hooked.

The beauty of the Keys certainly begins with her physical assets but at the root the beauty comes from the diverse people she attracts.  I set out in 2008 to experience both first hand by walking.  I struck on the idea of taking a picture and blogging from every mile marker.  For those of you who do not know, we have one major road running the length of the Keys, The Overseas Highway.  Each mile is marked with the traditional green roadside sign, except in The Conch Republic our mile markers become our most important landmark, with the final MM 0 sign in downtown Key West.  In order to share this adventure with you I decided to interview myself.  Here’s the result.  Enjoy.

Me: Carl, hi.  Thanks for the taking the time to talk to us about how to walk the entire 106 miles of the Florida Keys.

Carl: No sweat, happy to be here and share my experience with you Carl.

Me: Great, so I’ve got a few questions written down here on my crib sheet.  Shall we jump right in?  First question is how long did it take and why did you do it?

Carl:  I started the walk on 3 January, just after the New Year.  I walked into Key West and MM 0 on 19 January. So that’s 16 days for you math geniuses.  I did the walk alone.

Carl - 106 Mile Keys Walk - Campsite

Carl - 106 Mile Keys Walk - Campsite ©2008 Carlton Grooms

The walk had two, maybe three goals in mind.  First, I was turning 40 years old on 19 January and wanted to finish out my 30’s with a bang.  Second, I was in conversations with The Travel Channel for them to pick it up as show concept.  Third, I just really love the Florida Keys and wanted to see all of them up close and personal.

Me: Wow, 16 days alone in the Keys.  Cool.  What’s up with The Travel Channel thing?

Carl: In 2005 I took a one-year trip around the world with my family.  Took the kids out of school, the whole thing.  We did a book called, “Portraits of Our World” which we have since published and are selling.  All the profits are going to build schools in Africa.  I think the trip gave me some credentials with them.

During the trip around the world, I learned that if you don’t walk around a new place, you miss so much.  If you want to get into the local vibe you need to be on your feet with an mind open.  The Keys walk idea was meant to be the first walk in a series.  Like a pilot.

Carl - 106 Mile Keys Walk - MM 54

Carl - 106 Mile Keys Walk - MM 54 ©2008 Carlton Grooms

Me:  So did you have a camera crew?  You said you did it alone.

Carl: No I did all the shooting by myself.  I was self-sufficient.  I carried 85lbs of gear in my backpack and an HD camera strapped to my chest.  Before you ask the next logical question, the answer is no.  The Travel Channel never bought the pilot and I still have the entire show unedited waiting for the day to pitch the concept again.


Me:  Dude, that really sucks.

Carl:  No, not really.  I was out there for more than the show.  I was out there to spend some time with me.  Kind of like Jimmy Buffett’s song, “When the Coast is Clear”.  Turning 40 was a big milestone for many people, I wanted to make sure I did it right.

Carl - 106 Mile Keys Walk - Flying in Marathon

Carl - 106 Mile Keys Walk - Flying in Marathon ©2008 Carlton Grooms

Me:  Okay, enough of the show stuff.  Where did you stay?  What were your favorite hotels?

Carl:  I camped every night that I could.  In some places in the upper Keys there are gaps where you are forced into a hotel.  On some days I just couldn’t make the miles between camps either.  I averaged about five miles per day.

Me: So all your camping gear was in that pack too?  How was all that to carry?

Carl:  I wanted to camp because I want people to know that going the real Florida Keys is not about costing a lot of money.  You can keep it real and have the experience of your life.  It’s true about travel in general.  You don’t’ have to spend a lot of money to create life experiences in a new place.

I blogged on my website, Keyswalk.com. I reposted it recently so people can see it again.  I blogged via my iPhone every mile maker and took a picture of myself next to it.  That was fun and kept me focused.

Carl - 106 Mile Keys Walk - MM36 Rainy Day

Carl - 106 Mile Keys Walk - MM36 Rainy Day ©2008 Carlton Grooms

Me: Cool, so you blogged along the way.  Did many people follow you?

Carl:  Yes, actually.  I know Steve Huntington from Radio Margaritaville.  We go back to 1999 together.  I broadcast Radio Margaritaville when it was only on the Internet.  So we worked together.  He’s a super great guy by the way.  Though he took my wife out to lunch more than me.  Something fishy going on there.

I called Steve up and asked if Radio Margaritaville would follow me.  He agreed.  Carson Cooper called me every few days and checked in to see my progress and get an update.  He asked me each time for a Jimmy Buffett song I wanted to hear.  I remember asking him one day for an old one I love that fit, “God Don’t Own a Car”. I think they played, “A Pirate Looks at 40” for me on the 19th as I walked into Key West.

Me: What was the biggest challenge and biggest reward of the walk?

Carl: The biggest challenge was carrying the weight of the pack every day and still having the energy to be creative and shoot.  The biggest reward was all the really cool people I met along the way.

The Keys are beautiful but it is the people the Keys attract that are the best for me.  I met homeless guys leaving the Keys, newly married couples moving down from Ohio, a pair running a local bar, an 85 year old lady who spent most of her adult years in the Keys who had a pet dolphin.  Just an amazing cross section.  Everyone treated me like a long lost friend.


Me:  Bars.  Certainly you uncovered some cool places to drink?

Carl:  True.  When you walk everywhere you get real sense of place and you tend to look around more, look around corners more.  In reality I didn’t have much time or energy to get loaded every night because of the early rises and exertion of the daily walk.  I did become a regular for a time at Rob’s Island Grill in Big Pine Key.  It’s since changed hands and names.  Rob and Rachel were real good to me.  I really enjoyed the Tiki Hut at the campground in Marathon just before you cross the 7-mile bridge.

Me: You walked the bridge with traffic on it?

Carl:  Yes.  There are actually forty-two bridges connecting the Keys.  Obviously the 7-mile bridge is the longest.  This is the only stretch I did not carry my pack for safety reasons.  A guy I met drove it across for me in his pickup.  When you walk against traffic you are only two feet or so from passing cars doing 55 mph.  I wore a safety vest and was ready to jump if I had to.  Not sure that would have solved anything.

Carl - 106 Mile Keys Walk - 7-Mile Bridge

Carl - 106 Mile Keys Walk - 7-Mile Bridge ©2008 Carlton Grooms

It really is beautiful to walk.  The blues are every hue and the water so clear you can see the sea life.  There are a lot of boats out there to wave to and the air smells so clean.  If it weren’t for the danger I’d recommend everyone do it.  I’ve actually crossed it three times now on foot.

Me: Wow that really sounds nice.  What advice could you give our readers if they wanted to this?

Carl:  If you want to walk give yourself two weeks so you can enjoy it.  Plan your weight carefully.  I’d stay below 45 lbs.  Don’t carry cotton clothing as you’ll have weight and laundry issues.  Stay with more high tech cloth that can be easily hand washed.

Carl - 106 Mile Keys Walk - MM 0 The End!

Carl - 106 Mile Keys Walk - MM 0 The End! ©2008 Carlton Grooms

Biking could be fun; I haven’t personally done the length that way.  I’ve run it twice in a relay.  My favorite is the Keys100 run every May.  Bob Becker puts it on and does a great job.  There are individual ultra races at 100 miles and 50 (I tried the 50 last year and DNF’d at the mid way mark).  There is also a team relay for 100.  The relay is a total blast.  It should only take about 12 hours.  Then you are in Key West!

Overall walking the Keys is the best way to get to know the real Keys.  Each bridge, island, business or attraction can easily be observed as you stroll by.  At the slow speed you can also meet many more people. You also get some much needed alone time, which can be valuable given today’s connected world.

To top the whole experience off you are in Key West when you are done!


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Carl - 106 Mile Keys Walk - Key West

Carl - 106 Mile Keys Walk - Key West ©2008 Carlton Grooms


4 Responses to “106 Reasons to Walk The Florida Keys”

  1. Damon @ Let's Tiki May 1, 2011 at 11:58 pm #

    Great article. That sounds like a fun adventure. I know a lot gets missed driving.

  2. Carl Grooms May 2, 2011 at 9:06 am #

    Damon. Thanks for the note. I need to bike it now and have all the modes covered. I could hit more bars that way too.

  3. Skippy February 21, 2012 at 8:40 pm #

    I walked from mm 100 to mm 0 over 8 days in March 2010. Definitely a different way to see the keys.

    • Carl Grooms
      Carl Grooms February 23, 2012 at 11:25 am #

      Enjoy Skippy. It’s a ton of fun.

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