Sailing the US Virgin Islands: What It’s Like to Charter a Boat

My mom recently had a milestone birthday, and since she loves snorkeling and sailing, my parents and I celebrated by chartering a sailboat in the US Virgin Islands. This is something that’s been on my bucket list for years and it did not disappoint. We had the dreamiest week island-hopping on board our charter yacht Kai.

Our charter sailboat Kai

Our itinerary included the four main US Virgin Islands of St. Thomas, St. John, St. Croix and Water Island, with overnight stops in the following places:

  • Brewer’s Bay (St. Thomas)
  • Christmas Cove (on what used to be Epstein’s infamous private island and is now for sale for a cool $125M if anyone is looking to buy an island 😉)
  • Maho Bay (St. John)
  • Hansen Beach (St. John)
  • A private snorkeling spot our captain knew off the coast of St. Croix
  • Christiansted and Protestant Cay (St. Croix)
  • Honeymoon Beach (Water Island)

A boat was the perfect vantage point from which to take in the gorgeous coastal scenery as well as the stunning turquoise water, which was among the clearest I’ve ever seen anywhere.

Views from our sailboat in Brewer's Bay, St. Thomas, US Virgin Islands
Views from our sailboat at Christmas Cove, US Virgin Islands
Hansen Beach, St. John, US Virgin Islands

We expected the snorkeling to be good, but were absolutely spoiled by how amazing it was, especially the sea turtle and string ray sightings, which were a near-daily occurrence. My favorite stops for wildlife were Maho Bay on St. John (where it’s almost impossible not to see a turtle) and Protestant Cay on St. Croix, where I saw both sting rays and sea turtles, as well as the large green iguanas that hang around the beach.

A sea turtle seen while snorkeling in the US Virgin Islands
A string ray seen while snorkeling in the US Virgin Islands
A sea turtle seen while snorkeling in the US Virgin Islands
An iguana at Protestant Cay in St. Croix, US Virgin Islands
A turtle seen while snorkeling at Maho Bay, St. John US Virgin Islands

After a long day of snorkeling and swimming, it was so relaxing to sit on the deck with a good book and watch the sunset. A few nights our captain turned on the boat’s lights after dark so we could do a night snorkel, and one time we swam with several sting rays who were attracted to the light.

Sunset from our charter yacht in the US Virgin Islands
Sunset from our sailboat in the USVIs
Sunset from the boat in the US Virgin Islands

We booked Kai through Conch Charters. I can’t say enough good things about Kai and her crew (captain Justin, chef/first mate Maddie and second mate Sam the dog, who we all fell in love with) as well as the booking process with Conch. Everything exceeded our very high expectations, and Kai was the best home for the week.

Sam, the "second mate" on our charter yacht Kai

Below deck, Kai had three guest cabins, the salon, and the galley where Chef Maddie made our amazing meals. While yachts obviously aren’t like cruise ships with an endless quantity and variety of food offered, we filled out preference sheets in advance communicating our likes and dislikes, and Maddie did a great job accommodating our diverse group, even offering two main dishes some nights to accommodate both our seafood-lovers and our seafood-hater. I was so impressed with what she was able to whip up on a boat.

Below deck areas of Kai, our charter yacht
The meals prepared by Chef Maddie on our sailboat Kai

Above deck, we had two deck areas for relaxing, and the cockpit where we camped out during the rougher sailing days. We had to motor a lot when we were close to the British Virgin Islands (to avoid crossing into BVI waters, which was illegal at the time of our trip because of Covid restrictions), but we had two days in transit to and from St. Croix where we got to experience hours of open water sailing, which was a real thrill.

The cockpit of Kai, the sailaboat we chartered in the US Virgin Islands
Racing our sister ship Quest back home from St. Croix

The US Virgin Islands are such a beautiful slice of paradise and I can’t wait to come back again some day and spend more time here.

View of the US Virgin Islands from the airplane

It was also a real treat to spend so much time with just my parents, which is a rarity at this age and stage of life.

Our family on the boat

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