St. Thomas | Winter Escapes

It’s so difficult to make it through the winter for me, especially this particular winter. I know it could be worse, since I don’t live in Boston, but it could also be so much better! In previous years, my winter escape was St. Thomas, made easy by the fact that one of my friends has a house down there. We went two “spring breaks” in a row and had the times of our lives.


I hope that everyone has a chance to visit this little island paradise that I hold so dear in my heart, mostly because it reminds me of when I was in my prime. I was in my mid-20s, had just moved to the city, and nothing could stop me. I can’t recommend that you follow in our footsteps for *everything* that happened on our trips to St. Thomas – being locked out of the house because of a dip in the ocean after a night at the bars especially comes to mind – but you *must* do the following:

Go to potentially¬†my favorite bar in the world, Duffy’s Love Shack. Duffy’s is one of the diviest dives you will ever go to – it is physically located in the middle of a parking lot. All nights are themed and you receive a new pair of sunglasses, a lei, or a Michael Jackson glove each time you go – and you will go every night of your vacation. Drinks are about $1 and strong as anything. Just don’t order the lobster there. They will snort at you if you ask for garlic butter – because why would a restaurant have garlic? And one of their waiters may get annoyed at your group even after he lets you color in his outlined flower with a ballpoint pen. And if one of you says something mean to him, he may reply with “I’ve been called a lot worse, by a lot better.” And you may laugh about that line for the next five years.


Make friends with everyone else on the island – especially if they have cute Midwestern accents and are easy on the eyes. Meet up with them everywhere, even when you aren’t meaning to. Have a vacation romance or two. Also make friends with your local iguanas. Give them inappropriate names.


Stay up to watch the sunrise.


Take the ferry over to St. John to visit Trunk Bay, often voted as one of the best beaches in the world. Considering it’s so beautiful and pristine, it was pretty empty when we went. Drink coconut water straight from the source. Head to the bars on the island in the afternoon. Prepare to become intoxicated faster and harder than you’ve ever been before.


Visit Magen’s Bay on St. Thomas, also often categorized as one of the world’s best beaches, though less beautiful than Trunk Bay, in my opinion.


Wear sunscreen. That USVI sun is strong. Don’t forget any spots, especially the first day or you will feel it (and look it) for the rest of the trip.


Dance. Giggle. Have a blast.


Writing about St. Thomas certainly has me itching for another visit to the Caribbean, especially while listening to the forecast for the 390th snowstorm this season. While I often say I’d prefer to visit new places before I return anywhere, I would absolutely go to St. Thomas a third time, even though I’m no longer in my prime.


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