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Sailing The British Islands A Complete Guide For Singles Travelers

September 22, 2025 by kevinwilkerson Leave a Comment

Sailing the Virgin Islands British Virgin Islands BVIs
This is a must-stop destination in the BVIs, the tiny island of Sandy Spit. Photo: PubClub.com

By Kevin Wilkerson, PubClub.com Travel Blogger

Before my first trip to the Virgin Islands, I envisioned it being just like that Alan Alda movie, The Four Seasons, where some seasoned skipper would have us sailing through those turquoise-blue waters and pulling up to drop anchor by blinding white beaches while a bouncy blonde identical to Bess Armstrong would have me in full bliss the entire time. 

Unfortunately, in the Virgin Islands, you pretty much have to bring your own Bess Armstrong, for this isn’t exactly the Greek Islands when it comes to the singles scene.

Bess Armstrong The Four Seasons
Bess Armstrong on a Virgin Islands boat in the movie The Four Seasons.

Now you can find romance anywhere in the world and sometimes it comes when you least expect it. Still, in the BVIs you’re best advised to bring sand to those beaches.

Now if you’re a girl, especially a good-looking one, you can have a field day.  Pick of the litter.  It’s easy to find a captain and go sailing off into the sunset. I have a friend who is attractive (and even more so in a bikini) who signed up for a Windjammer cruise. It took oh, about 30 seconds, for one of the crewmen to hit on her like a hurricane and after that cruise he invited her on the next week’s cruise for free. That’s life and when the boys outnumber the girls by about 10 to 1, it’s easy to be the center of attention. Although it can be a bit tiresome, I’m sure, to be approached time and time again. So guys, pick your spots and don’t be annoying.

Otherwise, sailing the islands – and the British Virgin Islands in particular – is a spectacular experience. There are some great beach bars in the BVIs. It’s really true that the rum is cheaper than the water so the drinks are strong. The water is super blue and clear, there’s fantastic diving and snorkeling. The fishing is great, too and you don’t even need to go anywhere. We just threw a line out of the sailboat when going between the island and we caught fresh fish to eat every night.

All that being stated, this article is titled “a complete guid for single travelers” so here’s my tips after having been there several times. This assumes you have a boat lined up and a captain who knows how to sail it. Tyinghat’s the best way to get around to all the islands rather than trying to rely on the ferry schedule. Click here for tips on sailing in the BVIs.

Sailing in the British Virgin Islands PubClub.com travel blogger Sandy Spit
I’m enjoying this sailboat journey in the BVIs. Photo: PubClub.com
British-Virgin-Islands-TheBaths-Beach-sailboats
Sailboats are anchored off the beach of The Baths in the BVIs. Photo: PubClub.com
Jolly Roger British Virgin Islands bars
Bartender pour rum drinks at the Fish n Lime in the British Virgin Islands. Photo: PubClub.com

• Fly Into Tortola (BVIs) or St. Thomas (USVIs). Both are small Caribbean outpost airports, particulary in Tortola. Be prepared for a long customs wait because they do things on thier own time. Pro’s Tip: Don’t get mad or upset becuase the more impatient nt you get, the longer they will make you wait.

• Be Sure And Have Your Passport. Even if you fly into St. Thomas you’ll need the passport to check into a customs office when you cross into British waters.

• Put Your Cell Phone On Airplane Mode When Sailing. Either that or pre-pay a for plan, because you cross into British waters without knowing it and you don’t huge want roaming charges.

• Get Rum. Cruzan is the rum of the Virgin Islands and it’s pretty good. I like the dark (gold) rum and WATCH OUT for the 151! Beers are pilsners and lagers. I like Presidente from the Dominican Republic the most. Red Stripe from Jamacia is also widely available and some people drink Carib from Trinadad and Tobago, tho I think it tastes a lot like Corona  which I don’t like that much.

• Go To These Bars In The Daytime. Foxy’s at Jost Van Dyke’s Great Harbor, the Soggy Dollar Bar in Jost’s White Bay (it created the Painkiller and Kenny Chesney hangs out there when he’s in the islands), Gertrude’s just down the sand from the Soggy Dollar for the Bushwacker, Willie T’s pirate ship off Treasure Island (home of the shot and where people – with or without their bathing suits on – jump off the stern) and the bar at the top of The Caves on Norman Island (this requires going through The Caves, a series of big rocks which is a great BVIs activity),

• Go To These Bars At Night. Bamba’s Surfside Shack on the far side of Tortola (home of the “mushroom tea” and where girls take off their underwear and hang from the bar), the Foxy’s (you might want to pace yourself if you go in the daytime), the Bitter End Yacht Club in Virgin Gorda’s Spanish Town, Pusser’s, the Fish n Lime and The Bat Cave on Tortola and the aforementioned Duffy’s Surf Shack in St. Thomas.

• Singles Tips. Don’t press it. There may or may not be others around you that catch your eye. If you meet someone great, but that should not determine whether or not you go to the Virgin Island and nor should it determine whether or not you had a great time. And even tho “women and water are in short supply” as Jimmy Buffett sang in “Manana,” there’s a lot of fun to be had in the Virgin Islands.

Virgin Islands Safety Tip

• If You’re In St. Thomas, Be Careful After Dark. The best bar on St. Thomas, Duffy’s Love Shack, is on the other side of the island and is safe but the tourist area can be dicey after the sun goes down.

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Filed Under: Virgin Islands Tagged With: best Virgin Islands bars at night, best Virgin Islands daytime bars, British Virgin Islands, sailing, Sailing The British Islands A Complete Guide For Singles Travelers, Singles, travel

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