Destination US Virgin Islands


Stern of a boat tied to the dock


A seven-day sailing itinerary and a nod to history as the USVI gets its charter vibe back. 

The first time we arrived in St. Thomas it was at night and the end of a long, wet, arduous sail from New York via Bermuda. It was December 1971. The lights on the hillside overlooking Charlotte Amalie were still shining and there was phosphorescence in the water as we let the anchor slip over the side. Life was good! 

Historically, St. Thomas was made a free port by the Danes in 1815 and in the following years became a shipping and distributing point for the entire West Indies. A largeThe Market at Casimir Square Historical photo part of this trade was channeled through the harbor and the town Charlotte Amalie flourished commercially and became very cosmopolitan, compared to its sister island of St. Croix (“the breadbasket of the Caribbean”) where plantation life continued until 1848 when a slave revolt prompted the abolition of slavery throughout the Danish West Indies. Fast forward to the late 1800’s early 1900’s the islands were devastated by several natural disasters leaving the town in need of major rebuilding and depending heavily on Denmark for financial support. Negotiations between Denmark and the USA continued for nearly 50 years before a final deal was struck for $25 million in 1917 toward the end of World War 1. 

The town of Charlotte Amalie still has many of the original Danish buildings.Sloops lined up at the dock historical photo Picturesque alleys and stairways lead you from large mansions on the hillside to traditional West Indian houses surrounded by gardens. It is against this background that the government have initiated an ambitious revitalization project that is targeted to restore the entire waterfront and to place it among the most stunning waterfront promenades of the world. The scope of the project considers the entire waterfront area including Main Street and envisions a Caribbean waterside environment with restaurants and shopping that builds on the intrinsic beauty of this historic Danish town. 

The US Virgin Islands are enjoying a tremendous growth in the yacht charter sector and according to government sources 2021 has been a record year with 2022 looking even stronger. The Moorings have established a base at Yacht Haven Grande, Dream Yacht Charters have moved into Compass Point Marina adding to the available inventory of the well-established fleets of Virgin Islands Yacht Charters in Compass Point, CYOA Yacht Charters in French Town and Island Yacht Charters at Red Hook. As a part of this new initiative, the government (DNR) are responding to the surge and installing new mooring fields in order to both preserve sensitive areas and facilitate chartering for cruising yachtsmen to the territory. 

Airlines are continuing to add airlift to the region, which is now serviced from the USA by American, Delta, Jet Blue, United, Spirit and Frontier along with a host of smaller airlines offering connections throughout the Caribbean. This magnitude of direct air access allows charterers to arrive on island and get directly on their boats (with drink in hand) by midafternoon, without the need for ferry or onward air travel connections. 

A sailing itinerary around St. Thomas and St. John offers the sailor an incredible choice of anchorages including time spent in the USVI National Park system of St. John.Boat at anchor Maho Bay As the saying goes, you only go around once in life, but which way you choose to go is up to you. Here is a typical seven-night itinerary: 

Day 1: Board your vessel at noon, provision and check out. Sail to Buck Island or direct to Christmas Cove. Snorkel Fish Cay and visit the floating Pizza Pi (in season). 

Day 2: Motor over to Lind Point and pick up a NPT mooring. Dinghy into Cruz Bay and visit the National Park Information Center. Hike one of the many trails or sail along the coast and pick up a mooring at Maho Bay. Enjoy the sunset, walk the beach and expect to be visited by turtles. 

Day 3: Snorkel at Mary’s Point then sail around to Leinster Bay. Snorkel at Watermelon Cay, hike the trail or spend a few hours Woman leaning in the doorway of Annaberg Cookhouseexploring the ruins of the Annaberg Plantation for a brief insight into plantation life on St. John. 

Day 4: Sail around the north shore of St. John and stop for lunch and a snorkel at Hurricane Hole or continue over to Coral Harbor and have lunch at Lime-Out Taco Bar, a swim in experience. A short sail takes you to Salt Pond Bay for the night. Pick up a mooring, hike the trail or snorkel. 

Diver swimming in a school of fishDay 5: For the energetic, a long hike to Reef Bay and the site of the famous Petroglyphs. For the rest of us a short hike or snorkel before a nice sail along the south coast, visit Lovango Cay or pick up a mooring at Trunk Bay and enjoy the snorkel trail. 

Day 6: Sail down the north coast of St. Thomas to Magens Bay, a deep well protected anchorage and enjoy a walk on the beach, snorkeling and an evening cocktail while you watch the sunset. 

Day 7: Sail west downwind along the north coast and around the westernAnnaberg Mill tip of St. Thomas and back toward Charlotte Amalie. Anchor in Brewers Bay for a swim and lunch or continue to Druif Bay on Water Island for the night. 

Day 8: Return the vessel by noon and head for the airport. 

Two weeks next time! 


Links:  Charter Connections 

Virgin Islands Yacht Charters:


Island Yacht Charters:  

The Moorings: 

Dream Yacht Charters -

See more of: