Nearly six years ago, a boyfriend and I took, what would become for me, the road trip of a lifetime.
Sixteen hundred miles to escape the chill of Southern Ontario on Christmas Break to the furthest point South we could travel, in order to guarantee the warmth. Nearly six years ago, I fell in love with Key West—and all it took were four days—four days of hoodies and jeans in what were unseasonably cold temperatures for our tropical getaway.
As life would have it, I lost the boyfriend shortly after, but not my pull to return to this incredible little island. Having traveled a fair amount through the Caribbean I tried to put my finger on what this strong desire to return was. Was it the destination itself? Was it the company? Would it all be the same if I returned? I needed to find out, but there was just one problem—I could never find a travel partner that was as keen as I was to return, nor had the time off to travel when I did. This was my dream after all, so no one quite felt the way I did about getting back to the island.
Naturally, my thoughts turned to the idea of taking the trip solo. Why was I waiting for a sidekick when I had traveled enough that surely I could do it on my own? Why was I putting my dreams and the things I loved on hold just because I didn’t have someone to travel with? These thoughts were only reaffirmed when I read the best selling book “Eat Pray Love” by Elizabeth Gilbert. Now I wanted my own “Eat Pray Love” adventure—but on a smaller scale…all in one place…that little island in the Florida Keys that had etched its name on my heart. I imagined myself in a historical home, with a bike, a basket, and all of the fish tacos my stomach could handle—living the island life.
Thus, began the virtual vacation planning—FIVE years of virtual vacation planning. Every road, inn, restaurant, bar, excursion, attraction, etc., you name it, and it was likely I could give you all of the specs.
Unfortunately, I still didn’t feel brave enough, ready enough, to do it on my own during that time. What if I was sad I had to go it alone? What if I got lonely? Or worse still, what if I had created this island paradise in my mind and it was nothing like I had remembered the years previous? I had never even gone to camp as a kid. I had always enjoyed my own company, but always in the comfort of my hometown, where friends and family were just a phone call and a few minutes away.
This past Christmas (December 2014), the tug at my soul to return became so strong I could stand it no longer. I needed to get this dream out of my system so I could dream a new one, or perhaps, even make this one grow. I took the plunge and booked my first, what I have now coined, SOULo trip to Key West—baby steps, with a three night stay in a beautiful bed and breakfast in Old Town. Arriving via the Key West Express Ferry out of Fort Myers Beach, I can tell you this trip, from start to finish, was nothing short of magical. If you can imagine the little yellow Google person that you drag and drop to streetview (or rather, mermaid, when you search Key West—yes, you need to try it!), I was that girl. I guess that’s just what happens when you bring a dream to life.
A quote from Paulo Coehlo’s “The Alchemist” comes to mind:
“When you want something, all the universe conspires in helping you to achieve it.”
From the people that I met and the conversations that we shared, to the beautiful sights and experiences I encountered, it was clear I had made the right decision. The synchronicities were endless and it all felt good in my soul. In only four short days, I had made new friends, and there wasn’t a meal I sat down to alone. It all felt so good, I returned for five nights in March and, just recently, the entire month of July—in my own little apartment in a beautiful historical Conch home in the Seaport.
You can learn a lot about yourself when you take yourself out of your comfort zone and have only yourself to rely on. It becomes “GrOw” time. The longer you stay, the more feelings you will encounter. Some days will be long on your own; others will fly by with new adventures that you don’t want to end. They’ll be days you feel empowered and other days you’ll need a stranger’s “You’re so brave!”, while sitting at happy hour chatting away, to lift you back up again.
One thing I know is clear, traveling to Key West, as a woman, has felt safe and rewarding. What better place to feed your island soul both literally and figuratively. Nothing needed but your suitcase, your walking feet and a willingness to be open to whatever experience is meant to be for you. You may return with a heavier suitcase full of island treasures, but your soul will be lighter for it. If you dream of coming to the Keys and are inspired to do it SOULo—Key West will most definitely bring the magic!
Sherri in Paradise 
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