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Join us for your bespoke day upon the water!

Enjoy the stability, ample cushioned seating & classic lines of The Drinkwater, a 50ft Gulfstar, St. John's largest, most luxurious sailing yacht experience.

Join Captain Matt for a guided snorkel experience, drive the yacht under his supervision if you wish, or simply enjoy a pampered day on the crystal clear waters of the Virgin Islands.


All snorkel gear is provided, just bring your towel, a smile, and prepare to be spoiled


Our Story



Thanks for visiting our website, and we hope to have you aboard soon for a lovely day on The Drinkwater!


About us:


Tmana and I were married on St. John, our adopted home, in 2015. We honeymooned by sailing on a small sailboat from Florida to the Virgin Islands on a 6 month cruise through the Bahamas, Turks & Caicos, Dominican Republic, Puerto Rico, and the Spanish Virgin Islands.

Originally from Massachusetts, my family traces their lineage back to the Mayflower and has strong generational maritime ties in Yarmouth Maine where the Drinkwater family has a legacy of operating sailing schooners, fishing vessels and the Drinkwater Inn, near Portland.

I grew up spending summers on Cape Cod where I learned to sail from a young age aboard my family’s boats and graduated to larger sailing yachts when I moved to St. John in 2003.


Eventually, I obtained my Captain's License and have since logged over 65,000 nautical miles over two decades on sailing and motor yachts up to 114ft.

I've crossed the Atlantic twice, sailed the Pacific, throughout the Bahamas, Caribbean, and the Mediterranean Sea.

An accomplished sailor in her own right, Tmana has sailed over 5,000 nautical miles including several offshore passages.

Together, we have sailed thousands of miles and genuinely love creating new and memorable experiences for our guests through our passions for sailing, nature, and travel.

We hope to see you soon aboard The Drinkwater!


Proud charitable supporters of:

St. John ACC Logo
Friends of the Park Logo
Gift Hill School Logo
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