My First Solo Adventure


Arrival in St. Thomas

If you read my earlier post, “A Selfish Pact”, you know I promised the story of my first solo trip to take advantage of the fact that my kids went on vacation with my ex-husband.

It took all of 3.2 seconds after he told me he was taking the kids away to start Googling trip options. I’ve been to St. Thomas and St. John before, and I love both places. I watch “Caribbean Life” on HGTV religiously and secretly plan when I can make my own move to paradise. I realized I should start exploring the places I dream about moving to, so I decided on St. Thomas. Plus, a relatively affordable, non-stop, short flight make it a great destination for a short trip.

I wanted to get a little more of a local feel for my first solo trip so I decided to forgo the resort experience and try AirBnB for the first time. I searched for something centrally located with plenty of options for food, drinks, and fun because I didn’t want to rent a car. I focused my attention on the East End, knowing there is also a passenger ferry to St. John there, which afforded me even more options.

I stumbled upon a listing for a “floating condo” on AirBnB and was immediately intrigued. After reading nothing but gleaming reviews, I messaged Jeremy with a couple of questions, and decided to book my getaway on The ElSea. Jeremy is a character to say the least, and is living a fascinating life. Staying on a sailboat docked at The American Yacht Harbor brought the adventure level up a notch or two.

The ElSea

I scheduled a paddle boarding, snorkeling, and hiking adventure with Virgin Island EcoTours for my first full day. I shared my adventure with a nice family of four from North Jersey, and I should apologize to them now since I am probably in all of their vacation photos. One of the pitfalls of traveling alone and planning excursions like this one is you really don’t know who you’ll end up spending the day with, but I had nothing but amazing experiences with everyone I “shared” my trip with. Yosh, our guide, was a super chill guy with an astounding amount of local knowledge. I highly recommend spending a day in the mangroves if you have the chance.

Several of my evenings were spent sitting at the bar at Fish Tails in Red Hook. The food, drinks, and staff were all outstanding. Sally and Kelley made me feel extremely comfortable, and I can’t wait to go back to visit them again soon.


Thanks to Jeremy, I spent the longest and most incredible beach day at Secret Harbour Beach Resort. My lunch and drinks at The Cruzan Beach Club right on the beach at the resort were fantastic, and the beach, the water, the snorkeling, and the sunset at Secret Harbour were all unparalleled.

My favorite day was my final full day spent with a varied and amazing group of people on a day trip with Hakuna Matata Sailing Charters. Kelly and Dawn are skilled sailors with a gorgeous vessel and one of the most beautiful playgrounds in the world as their office. Not only were the scenery, sailing, homemade lunch, and snorkeling top-notch, but the other guests and Kelly and Dawn made the whole day an experience I won’t soon forget. We had an ecclectic bunch composed of a local and his brother, a sweet young couple from Washington State, and a brand new transplant to St. Thomas via Denver. I feel like I came away from my day sail with not only wonderful memories and beautiful photos, but also some really interesting new friends.

Christmas Cove

My solo trip was one of the most adventurous experiences of my life. It may not seem like a big deal to anyone else, but setting off on a solo trip and staying on a “boatel” were not in my wheelhouse. I definitely stretched the boundaries of my comfort zone, and I’m so glad I did! I can’t wait for the next adventure…

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