Traveling SOULo: The Magic of Key West

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.

sherri4As 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.

sherri2Unfortunately, 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.”

sherri3From 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!

P.S. – If you’d like to hear more specifics about my adventures in Key West, stayed tuned, as I hope to share more and inspire others as a part of Island Jane’s International Team!

Teacher, writer, and passionate creative mind, Sherri calls Southern Ontario home, but has a special soul connection with the island life and a great love for the Southernmost Point of the US–Key West, FL. Her love for the water started at an early age, splashing in Lake St. Clair–the “Heart of the Great Lakes” and international boundary between the US (MI) and Canada (ON). Being on, in, or by the water via the beach, dock or pleasure craft are favorite pastimes. She loves traveling, ocean life (including mermaids!), and, of course, her “Sweetwater Sea” in the North. Sherri enjoys inspiring others and sharing the happenings of a “Meandering Mermaid” from this small, but big-hearted, body of water as part of the Island Jane International Team.


  1. Thank you for this wonderful article!! Sherri walked in The Captain’s Mermaid Boutique during her March visit and she was an instant hit with myself and my daughters!! Her contagious enthusiasm is …..well contagious!! She is what a Fresh Water Conch is all about …..she came to visit and stayed or at least her heart did! She is a wonderful person and look forward to seeing her happy face soon!!

  2. Thanks Ana! She is a gem, we love her too 🙂 I think Key West is in her blood now, I bet it won’t be long until she’s down here full time.

  3. Just a response to say we all miss her not so far here “up north” But so happy that Sheri has landed in such a caring and wonderful spot. I, myself am a teacher who taught with Sheri, and I plan to retire this June. Maybe a visit to this amazing place is in my/our future too. Great article & take care of our little expat until we get there.

  4. Enjoyed the article..rings so many bells with me..heading down in 2 weeks 3rd solo trip in 2 years..just can’t stay away 🌴💛

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