Best US Virgin Islands Bar Crawls — Our Top 4

1.Cocktail Sunset Cruise from Sapphire Beach Resort

★★★★★★★★★★5.0 · 748 reviews · from $130Our pick

Sail from Sapphire Beach Marina for about two hours aboard New Horizons & Breakaway Charters. You’ll cruise beyond St. Thomas and around nearby keys, hear island commentary, enjoy Champagne, unlimited drinks, appetizers, and music, then return to the marina. Crew members may include Nate, Max, Whitney, Breezy, or Captain Stewart.

“Friendly and knowledgeable captain and crew mate! Appetizers were delicious and sunset and surroundings were spectacular! Oh I forgot best painkiller I have had 🥇 would highly recommend this cruise!!”

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2.Sunset Sail with Cocktails and Appetizers

★★★★★★★★★★5.0 · 580 reviews · from $95Best value

Spend about two hours aboard The VI Cat, a 54-foot catamaran sailing around Charlotte Amalie Harbor from Marriott’s Frenchman’s Cove. The crew serves cocktails, wine, beer, soft drinks, and light snacks such as fruit, cheese, hummus, pita, and chips. Expect a relaxed, music-led cruise with sunset views, attentive service, and a return to the dock around dinner time.

“Big fun. Great crew. Perfect evening! Stunning views, smooth ride, and great vibes—best way to end a St. Thomas day.”

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3.Catamaran Sail to Jost Van Dyke (Soggy Dollar Bar)

★★★★★★★★★★5.0 · 139 reviews · from $375

Set sail from Red Hook with Stormy Pirates Boat Charters for a full day in the British Virgin Islands. You’ll cruise with up to 12 people, enjoy breakfast, unlimited mimosas and an open boat bar, visit Foxy’s in Great Harbor, then spend three hours at White Bay and the Soggy Dollar Bar. Bring a valid passport and $85 cash for customs.

“Great experience from the time we stepped on the boat til we left it. Suzanne and Ken are wonderful!”

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4.St. John Sail with Bar and Hors d’Oeuvres to Lovango Dinner

★★★★★★★★★★4.5 · 35 reviews · from $119

Leave The Westin St. John at 5:15 p.m. aboard a catamaran for Lovango Cay. Enjoy cocktails and appetizers at sea, then buy dinner at Lovango Resort and Beach Club. The return includes an open bar, cordials, dessert, and star-filled views. Crew members may include Captain Erin, Anna, Brian, Alexi, or Riley.

“Friendly staff. Delicious hor d’oeuvres. Killer Painkillers. Great meal at Lovango. I would highly recommend.”

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