St. Thomas itinerary: sailing days from a house on land

How a sailing week works from a St. Thomas house

A charter's sample week has you sleeping on the boat. From a house, the shape changes: you sail by day and come home at night, so the boat days can follow the wind and the swell, and the land days fill the gaps. Three water days are enough to see the cays, the National Park on St. John and the British Virgin Islands. The other four are beaches and towns, each a short drive.

The rules on the water belong to four authorities, and a captain will know them; it helps if you do too. The National Park Service sets the moorings around St. John and part of Hassel Island, the US Fish and Wildlife Service keeps Buck Island closed, the Department of Planning and Natural Resources (DPNR) manages the reserves of the East End, and the British Virgin Islands set their own border.

Days one and two: arrival and the north side

Cyril E. King airport is on the west end of St. Thomas. From the terminal, Charlotte Amalie is 12 minutes by car and Red Hook, on the East End, 36. Where the house sits decides the rest of the week: the boats to St. John and the BVI leave from the east, the Water Island Ferry from the west.

Spend the second day on the north side by car. Magens Bay is 14 minutes from Charlotte Amalie. Hull Bay, the free fishing-boat beach one bay west, is 12 minutes from town. Brewers Bay, by the university, is 13.

Day three: Water Island on the hourly ferry

Water Island is the closest of the boat days and needs no captain. The Water Island Ferry leaves Crown Bay Marina, 9 minutes by car from Charlotte Amalie, every hour from 7 am on weekdays, 8 am on Saturdays and 9 am on Sundays and holidays, as of October 2026 on its own timetable. A visitor pays $20 round trip, $10 a child.

From Phillips Landing, Honeymoon Beach is a 5-minute walk, with a bar on the sand that rents chairs and snorkel gear. The last boat back leaves Phillips Landing at 6:15 pm every day, on the operator's timetable as of October 2026. Miss it and there is no road home.

Day four: Hassel Island, Buck Island and Christmas Cove

This is the day sail along the south shore, and each stop has a different rule.

Hassel Island sits across Charlotte Amalie harbor from town, and part of it is inside Virgin Islands National Park. The park's 2026 Superintendent's Compendium limits boats docking at Careening Cove or the Creque Marine Railway to day use, and says visitors have limited places to land safely. Plan it as a stop with a walk, not a beach.

Buck Island is seen from the water. The whole 45-acre island has been a wildlife refuge since 1969, and it is closed to the public as of October 2026, per the US Fish and Wildlife Service. The refuge stops at sea level, so a boat stops off it and nobody goes ashore.

Christmas Cove lies against Great St. James, one of the three reserves DPNR lists in the St. Thomas East End Reserves, with Cas Cay and the Mangrove Lagoon and the Compass Point Salt Pond. DPNR's page sets out no mooring rule for the cove, so ask the captain what the boat will use.

Day five: St. John by ferry or by boat

By ferry, St. John is the easiest day of the week: the passenger boat from Red Hook to Cruz Bay takes about 20 minutes dock to dock, and Red Hook is 28 minutes by car from the Charlotte Amalie terminal. From Cruz Bay, Trunk Bay is about 13 minutes by car, and the National Park Service charges $5 a person aged 16 and over there, with no cash taken since October 1, 2026.

By boat, the park's rules apply. The Superintendent's Compendium says a boat of 60 feet or less may not anchor; it takes a white mooring with a blue stripe, and may use the Lind Point or Francis and Maho anchorages only when the moorings in Caneel Bay or Francis and Maho Bay are full. A night on a mooring is $26 per the National Park Service as of October 2026, and the Compendium lets a boat stay seven nights in one bay and 30 in a year.

Day six: sailing to the BVI with passports

The British Virgin Islands are British, and the passport-free trip ends at their line. The BVI Tourist Board says anyone arriving by air or sea must present a passport to enter and to depart, as of October 2026. On a family sail, that is a passport for every child.

Entry is at a customs and immigration office, and the Tourist Board lists four, open daily. The one on Jost Van Dyke, at Great Harbour, keeps the shortest hours, 8:30 am to 4:30 pm as of October 2026, so a boat that wants an afternoon there arrives early. Keep the passports aboard for the sail home.

Day seven: the East End beaches near Red Hook

Keep the last day close to the house and the airport run. Sapphire is about 4 minutes by car from Red Hook, and free and public as of October 2026. Secret Harbour is 6, open to the public with no day pass as of the same month. Coki is about 9, with no entrance fee as of October 2026, very little parking, and Coral World beside it.

The tradeoff of an East End base shows on the way out: the airport is 36 minutes from Red Hook, and longer on a cruise-ship day. Leave the beach by early afternoon for an evening flight.

A St. Thomas itinerary for 3, 4 or 5 days

A shorter stay keeps the days that cannot be done another way and drops the beaches you can reach any afternoon.

The BVI day is the one to book first and give up last, since it needs a passport for every traveler and a calm morning. Check the St. Thomas weather page for the month before you choose the days.