Dating While Traveling in St. Thomas

Interested in dating an island local in the Caribbean? Find out what dating is like for single female travelers in St. Thomas with this detailed account.

Part of the fun of being a single female traveler is dating while on holiday. My best friend, Ariel, and I just came back from 10 days in St. Thomas of the U.S. Virgin Islands. We can report that there isn’t anything virginal about the Caribbean.

Getting a Date While on Vacation

Finding someone to chill with is easy thanks to dating apps like OkCupid, Hinge, and Bumble (just to name a few). Just like when I was abroad in Ireland and looking for dates, Tinder became a convenient method to discover new people. However, dating on an island creates a more defined border unless your potential hookup has access to a boat.
Since Ariel and I went to a U.S. territory, we didn’t bother to bring our passports. However, with the British Virgin Islands just miles away, going on a date (or five) with an Englishmen would have just required ferry fare. Surprisingly, this island-jumping mentality was lost on the Brits and none of the potential gentlemen callers would come to our rock.
Note: Do not be surprised to see the same potentials on your travel buddy’s phone when using dating apps on an island.
In fact, one of the biggest problems with dating on vacation was that many natives didn’t want to date tourists. Many conversations would die following, “We’re here for a week.”
One night, Ariel and I were talking to a couple of guys at Bernie’s in Red Hook when a fiery-eyed woman started giving shit to one (her ex) for trying to fuck a tourist. To the local women of St. Thomas, Ariel and I are just pirates looking to steal their booty.

Perks of Being Single on Holiday

Spending 10 days drinking in St. Thomas would have been far more expensive if Ariel and I were not single. While we did not overtly request drinks, food and entertainment to be paid for, many of the men we kept company with obliged freely and without hesitation.
One of my friend’s goals on this trip was to go fishing on a boat. Charters in the U.S. Virgin Islands can cost $200 per person for a six-hour excursion. After speaking with a female bartender at Slice off Sapphire Beach, we met up with a couple of guys from Trinidad who fished on the island. We spend two days on their boat fishing, snorkeling, and going to St. John as well as drinking and smoking to our hearts’ content — all for free.

In addition to the aforementioned, they picked us up and dropped us off at our accommodations. The night before we left they took us out to a lovely Italian dinner at PesceAnd what did we have to do for such treatment? Absolutely nothing. Nobody kissed much less flirted.

What are locals like on St. Thomas?

Being from Cape Cod, Ariel has an affinity for boat captains (in addition to those blond and taller than six foot). The hand full of bars in Red Hook are filled with locals who perfectly match that description. If you are looking for a tall, tan, and lean 20-something who knows his way around a boat, then I recommend visiting the U.S. Virgin Islands.

We’re all captains here.”
– Super Hot Guy at Bernie’s Bar & Grill

Ariel’s face lit up like a child’s on Christmas morning. She had found her Shangri-La in a land of hard-bodied boys. Not only were these men attractive but they were also pretty well-mannered. I was surprised how none of them expected anything more than a nice conversation or a game of darts. Almost every night we were escorted safely back to our Airbnb without any expectations.
Note: Everyone knows everyone on a small island since there is a limited population.
If you are looking for a good time that involves rum, sun, and boys with boats, then St. Thomas is a great place to visit. Check out Red Hook for local favorites like Bernie’s, Duffy’s, XO, and Tap & Still in the evenings and beach bars, such as Sapphire Beach Bar and Shoreline Bar & Grill, during the day.

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