The US Virgin Islands: St. Thomas, St. John, St. Croix

Destination Guide · Caribbean · US Virgin Islands

The US Virgin Islands occupy an odd position in Caribbean sailing. As a US territory, they offer the regulatory simplicity of domestic cruising — no customs on arrival from the mainland, US dollar transactions, US Coast Guard jurisdiction, familiar grocery chains — while being geographically and culturally Caribbean. St. Thomas is the commercial and charter hub, built around the duty-free shopping in Charlotte Amalie and the charter fleets based at the marinas on the east end of the island. St. John, four miles east by ferry, is dominated by the Virgin Islands National Park, which covers two-thirds of the island's land area and most of the offshore cays, with mooring fields managed by the National Park Service. St. Croix, 40 miles south and separated from the St. Thomas-St. John pair by the Puerto Rico Trench, is the forgotten island — quieter, less visited, with a different character and the best reef diving in the USVI at Buck Island.

The USVI's primary significance for the cruising circuit is as the gateway to the BVI. From Cruz Bay on St. John, Road Town in Tortola is 9 miles. From the east end of St. Thomas, it is 12. The crossing is the most-sailed offshore passage in the Caribbean — a quick beat or beam reach that connects US regulatory waters with the British Virgin Islands and the deeper Eastern Caribbean beyond.

St. Thomas: The Commercial Hub

St. Thomas is a working port town in a way that St. John is not. Charlotte Amalie, the capital, is built around the duty-free commercial port — cruise ships dock here at the rate of four or five per day during peak season, and the town center is organized around the shopping that cruise passengers generate. Jewelers, liquor stores, electronics vendors, and the institutions that have served them since the island was a Danish colonial trading post fill the waterfront. For sailors, Charlotte Amalie offers full provisioning, the largest chandlery selection in the USVI, fuel, haul-out facilities at a couple of boatyards, and an anchorage that is convenient but exposed to ferry and cruise ship wash.

The American Yacht Harbor at Red Hook, on the east end of St. Thomas, is the sailing center of the island — closer to St. John, closer to the BVI, and with a marina community of charter operators, water taxi services, and the ferry terminal for St. John. The anchorage off Red Hook is one of the better protected on the island. The provisioning at the Pueblo supermarket near Red Hook is adequate for a stocking run; for a full provision, the Cost-U-Less in the east end shopping district is the better option.

St. Thomas customs for boats arriving from the BVI is processed at Charlotte Amalie or at the customs dock at Red Hook — the process is streamlined because this crossing is done hundreds of times per week. The USVI maintains a customs and border protection presence at both locations. Foreign-flagged vessels arriving from foreign countries (not just from the BVI) should confirm current clearance requirements, which have changed periodically.

Pillsbury Sound: The Crossing Between St. Thomas and St. John

The four miles of Pillsbury Sound between St. Thomas and St. John are among the most trafficked waters in the Caribbean. The Red Hook–Cruz Bay ferry runs every 30–45 minutes during the day; water taxis, day charter boats, and private vessels make the crossing continuously. The trades funnel through the Sound and accelerate in certain conditions, producing a steeper chop than the wind speed suggests. Crossing under sail requires attention to the ferry traffic, which runs on schedule regardless of what the wind is doing.

The current in Pillsbury Sound runs with the tides and the wind-driven flow, and can set a boat significantly north or south of the intended track on the short crossing. The ferry docks at both ends are active enough that a boat sailing across the Sound needs to be in clear sight of the ferry approach lanes at all times. This is not a difficult crossing, but it demands attention.

St. John: The National Park Island

St. John is two-thirds national park and one-third community — and the community is mostly in Cruz Bay on the west end, where the ferry docks, the customs office operates, and the provisioning that exists on the island is concentrated. Cruz Bay has changed significantly since the island became fashionable as a high-end resort destination in the 1990s and 2000s; what was a quiet village has become a small town of restaurants, rental car agencies, and boutique hotels. The anchorage in Cruz Bay is managed by the National Park Service with mooring balls and a reasonable fee structure.

The mooring fields at Caneel Bay, Hawksnest Bay, Trunk Bay, and Cinnamon Bay — all on the north shore of St. John — are NPS-managed and represent the best anchorages on the island. Trunk Bay, with its self-guided snorkeling trail marked by underwater signs along a coral reef, is the most-visited beach in the USVI and mooring field fills up by 10 am on any clear winter day. Caneel Bay, formerly the site of a Rockefeller-developed resort that closed after Maria, is in transition — the NPS controls the land, and what eventually gets built or doesn't built there will shape that anchorage's character for decades.

Coral Bay, on the east end of St. John, is the other St. John — calmer, more laid-back, with a cruiser community that has been anchored out in the bay for decades in some cases. The provisioning at Coral Bay is limited to a small market; the social scene at the handful of bars on the waterfront is the draw. Coral Bay is the jump-off for the BVI crossing in the other direction — the anchorage is 7 miles from Road Town, the closest USVI anchorage to Tortola.

The hiking on St. John from the anchorage is legitimate — the Reef Bay Trail drops from Centerline Road down to a beach with petroglyphs and a ruin of a sugar factory, and the trailhead is reachable by taxi from Cruz Bay. The trail is accessible in morning light before the heat becomes a problem. Bring water; the island is dry enough that the NPS trail markers include heat warnings.

St. Croix: The Forgotten Island

St. Croix sits 40 miles south of St. Thomas, accessible by seaplane or by the inter-island ferry that runs on a limited schedule. For boats, the passage from St. Thomas to St. Croix crosses the Puerto Rico Trench — the deepest point in the Atlantic Ocean, at over 28,000 feet — in waters that are exposed to Atlantic swell. The crossing is typically 6–8 hours and is rougher than the sheltered intra-USVI sailing; it is done by sailors who specifically want to see St. Croix, not as a stop on the way to somewhere else.

St. Croix rewards the passage. The island has a Danish colonial history — Frederiksted and Christiansted were both developed under Danish rule from the 1730s — and the architecture in Christiansted in particular is the most intact Danish colonial urban fabric outside of Denmark itself. The town is walkable, has good restaurants, and receives far fewer visitors than St. Thomas or St. John. The cruiser community at the Christiansted anchorage is small but established.

Buck Island, two miles northeast of St. Croix, is one of the finest snorkeling sites in the Caribbean. The Buck Island Reef National Monument encompasses the island and the surrounding reef, with an underwater snorkeling trail that takes you through an elkhorn coral barrier reef system. The anchorage off the west beach of Buck Island is protected in trade wind conditions; the NPS manages mooring balls on the northwest side. The coral at Buck Island is in better condition than most Caribbean reefs because the protected status has limited the damage. Plan a full day: snorkel the trail, eat aboard, snorkel again.

The Crossing to the BVI: Sir Francis Drake Channel

The passage from the USVI to the BVI is the most-made inter-territory crossing in the Caribbean. From Cruz Bay on St. John to Road Town on Tortola, the distance is 9 miles. From the east end of St. Thomas, it is 12. In trade wind conditions — the normal conditions from November through June — the crossing is a close fetch or beam reach from the USVI, the direction depending on the exact departure point and destination.

The Sir Francis Drake Channel, the body of water between Tortola to the north and the island chain (Norman, Peter, Cooper, Virgin Gorda) to the south, runs roughly east-west. The entrance from the USVI is from the west: a boat from Cruz Bay or Red Hook sails east, passes south of Little St. James Island (privately owned), and enters the Channel with Norman Island ahead to port and the BVI spreading out to the east. The navigation is straightforward; the traffic — ferries, day charters, private boats in both directions — requires attention in the first few miles.

Customs on arrival in the BVI is required regardless of where you have come from. The Q flag goes up at the USVI-BVI boundary and stays up until you have cleared in at Road Town or West End on Tortola. This formality is universal and enforced — BVI customs does check, particularly at the popular anchorages where private boats are obvious among the charter fleet.

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