Check Itinerary
Book Now
St. Thomas Sailing Trips aboard Heavenly Days, a custom-built and award-winning 53’ catamaran sailing out of Bolongo Bay in St. Thomas. Hop aboard to admire the sunset over the Caribbean Sea, visit neighboring St. John National Park, swim with sea turtles on our award-winning sail to Turtle Cove on Buck Island and experience beautiful Honeymoon Beach on Water Island. Charter a private sail for events and destination weddings on the Caribbean Sea!
Give the special gift of a sailing excursion in the Virgin Islands! Sailing right out of Bolongo Bay Beach Resort, the award-winning Heavenly Days Catamaran is one of the most convenient, affordable, and exciting ways to go sailing on the Caribbean Sea! Swim with turtles, dress up for our sunset cocktail sail, or join a island hoppin’ Sunday Funday sail!
This is one of the best and top-rated St. Thomas sailing trips. We were the first charter company to call our Buck Island tour a “swim with turtles” sail it’s become one of the most popular sailing experiences in the Caribbean.
Experience swimming with gentle sea turtles in their natural habitat. Take a sail to a specially protected anchorage. Snorkel, swim or just relax onboard. Sea Turtles are (almost) always a guaranteed sight – even from the deck! It is definitely an unforgettable three-hour tour. Cost includes snorkel gear, light snacks, soft drinks, beer and rum punch for after swimming and snorkeling.
For a magical start of your evening, come sailing with us through beautiful Charlotte Amalie Harbor and around Water Island. Watch the colors of the sky change over the Caribbean Sea and St. Thomas slowly light up. You will be back at our resort just in time for dinner.
(Note: This Trip Is Not Currently Offered) Take in the beauty of the crystal blue waters and experience the wonders of the national park of St. John.
Enjoy an unforgettable 6 hour tour to the enchanted island of St. John where you will have the opportunity to go ashore and enjoy beautiful Honeymoon Beach.
The two hour sail over takes you along the scenic south side of St. Thomas, through current cut on the eastern tip where the Caribbean and Atlantic oceans meet, and across Pillsbury sound where St. John beckons.
At our special anchorage you will have at least two hours to swim, snorkel, or just relax on the beach or on board. A vibrant coral reef os easily accessible. Snorkel gear, instruction and guided tour is provided. Sodas, juices, water are available throughout your tour, and after snorkeling there is a full bar available and a delicious deli-style buffet luncheon.
Sail from Bolongo Bay down the coast line of St. Thomas to to Honeymoon Beach on Water Island, the 4th and smallest of the US Virgin Islands. You will have plenty of time to enjoy the beach and snorkel gear is provided. Open bar is included on-board after snorkeling. Lunch can be purchased from local vendors on Water Island. Captains choice includes a stop for snorkeling on the way to Water Island.
Heavenly Days was designed in the glory days of performance day charter catamarans in the Caribbean. Simply put, nobody builds boats like her anymore, and there are very few left in the world. Performance in this era was paramount, and Heavenly Days and her counterparts revolutionized the Caribbean vacation experience. She sports an original rotating wing mast and her wood construction, a rarity these days, is a testament to her sound construction and meticulous care. Any avid sailor would respect her design, construction, and performance.
Ever since Bolongo first opened our doors in 1974, we’ve been pioneering new ways to let people discover the beauty of the Virgin islands at sea. Our guests get to experience sailing to St. John, Buck and Water Island; snorkeling shipwrecks; and swimming with sea turtles on our original award-winning trip. Bolongo Bay revolutionized the Caribbean resort sailing experience, and we've played a huge part in perfecting some of the island's most popular day sail excursions to this day. We can’t wait to have you on board.
Voted “Best Excursion of the Year in St. Thomas” among other honors.
© Copyright 2023 All Rights Reserved
