St. Thomas is the gateway to some of the world's finest sailing waters. With steady trade winds, protected channels, and dozens of anchorages within easy reach, a sailing trip from Charlotte Amalie opens up everything from the party bars of Jost Van Dyke to the deserted beaches of the outer cays. Here is how to spend three perfect days on the water.
Your 3-Day Sample Itinerary
Charlotte Amalie to Christmas Cove
Depart from the marina and sail east to Christmas Cove on Great St. James Island. Snorkel the reef, enjoy a pizza from Pizza Pi (a floating pizza boat), and watch the sunset from the cockpit.
Jost Van Dyke & Soggy Dollar Bar
Sail across the channel to Jost Van Dyke in the BVI. Anchor at White Bay and swim ashore to the legendary Soggy Dollar Bar, birthplace of the Painkiller cocktail. Explore the island on foot before a starlit dinner at Foxy's.
Norman Island & The Indians
Motor-sail to Norman Island — the inspiration for Treasure Island. Snorkel The Indians (dramatic rock pinnacles teeming with reef fish), then explore the Pirate's Bight restaurant built into the bay. Sail back to St. Thomas under a Caribbean sunset.
Ready for the full experience?
Get Your Complete St. Thomas Itinerary
This is just a taste. My Island Compass builds a full, personalized day-by-day itinerary based on your travel style, your group, and your pace — designed by a Caribbean family that lives here.
🌴 Plan My St. Thomas TripFree 2-day preview · No credit card required