Private Sailing Charters in the Virgin Islands

Private Sailing Charters in the Virgin Islands

Private Sailing Charters in the Virgin Islands

Private Sailing Charters in the Virgin Islands


Escape to a land of tropical beauty in the U.S. Virgin Islands. The three main islands—St. Croix, St. John and St. Thomas—offer a range of attractions best explored on the sailing vessel Lucky Me. Delight in the all-inclusive service of a professional captain and gourmet chef. You’ll have even more time to enjoy your guests and beautiful surroundings.

Diving & Snorkeling on Your Charter

No matter your scuba diving skill level, you can explore the beauty and fantastic world of the Caribbean’s underwater habitat on your private charter.

You captain is a certified divemaster who can take you to incredible diving and snorkeling locations around the Virgin Islands! Our guests are constantly raving about our dive locations and expertise of our captain.

Explore corals and gorgonian forests of sea fans and sea whips. Dive around caves, explore sunken boat wrecks or take a night dive and explore the fantastic world of nocturnal marine life! Swim among turtles, bright parrotfish and blue tang in the clear waters of the Caribbean.


The Lucky Me catamaran is a U.S. Flagged vessel in St. Thomas in the USVI. This location offers a unique combination of steady trade winds, sheltered waters, short passages, and protected bays and sounds. Enjoy it all with the carefree ease of having a professional captain and chef to take care of operating the yacht.

The trade winds generally average 10 to 20 knots most of the year, making this region superb for a relaxed holiday with all the satisfaction that comes from enjoying time on the water under sail. Temperatures average between 74°F and 87°F (24°C – 31°C).

Immerse yourself in the underwater world of vibrant coral and diverse marine life in the cobalt blue waters of the Caribbean. Dine on fresh, local cuisine prepared just the way you like by your gourmet chef. Enjoy some of the best shopping in the Caribbean with hundreds of duty-free stores throughout the islands, or just relax and gaze at that signature Caribbean sunset. It’s all here and it’s all yours to enjoy on your yacht charter.

Lucky Me anchored right off shore of an island

See Why Our Guests Love Sailing Aboard Lucky Me

No amount of words will do justice

The trip 6 of us had the unbelievable pleasure of booking with Michael and Jes. They are the best captains and team on the sea. I had expressed to Michael that we love “non tourist” spots, but also wanted to see the can’t be missed spots. They accommodated our dreams by taking us to wonderful places; I truly felt they were as excited as we were. We visited 11 islands in 7 days.

– Stacy B., Facebook Reviews
Incredible Trip with S/V Lucky Me

Captain Michael and Chef Jes (she’s a captain too) are an amazing couple who love being on the water, love to teach you things and see all the wonders under the ocean. If you are looking for the perfect blend of romantic getaway or a family fun vacation, relaxation and a beautiful backdrop, a trip with the crew of S/V Lucky Me is just where you need to be!!

– Tim W., TripAdvisor
It was the perfect vacation!

Every day was a different experience. We had so many laughs and experienced so many things. Michael and Jes went above and beyond for all of us. Jes is an amazing chef and captain. Michael is a wonderful Captain and shared so much knowledge of every island we went to and more. Make this a vacation goal for sure. You won’t regret it.

– Mary-Alice H., Facebook Reviews
Sailing the Grenadines

We had the best time getting to know Captain Michael and Chef Jes on this off season get away. The yacht is amazing and only takes a second place to Chef Jes's food! Every need was met with a smile and cold drink and being able to dive with such an experienced crew was also a bonus. The cabins felt more like a luxury hotel suite than a boat and the saloon was huge and welcoming.

– msfixit615, TripAdvisor
Everything we dreamt it would be

We had a wonderful sail/dive with Mike and Jes 5 days/4 nights for a party of four. We did full-board and the food was awesome. Jes is an excellent chef, prepped a creative and fun menu and displayed flawless execution. They run a first class dive operation on their boat, and we felt very comfortable in their capable hands... The trip was everything we dreamt it would be, and we hope to join them again!

– Daniel M., Facebook Reviews

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