USVI Sailing Itinerary: 7-Day Crewed Charter, St. Thomas to BVI

After landing at Cyril E. King Airport in St. Thomas, your adventure begins with a short taxi ride to the marina—either Yacht Haven Grande or American Yacht Harbor in Red Hook. Here, you'll be warmly welcomed by your professional crew and shown aboard your luxurious yacht. Settle in, enjoy a refreshing drink, and let the relaxation begin.

Once you're ready, your crew will get underway for a short sail to the breathtaking National Park beaches of St. John. Spend your first evening anchored off one of the island's pristine beaches. Maho Beach is a favorite for its serene waters and near-guaranteed turtle sightings, while Trunk Bay, considered one of the world's most famous beaches, offers stunning views and powdery white sand.

Unwind, take a dip in the turquoise waters, and enjoy a chef-prepared dinner under the stars as you embrace the start of your unforgettable journey.

After a peaceful start to your morning, your captain will handle clearing customs at the West End of Tortola while you relax aboard. With the paperwork sorted, your adventure in the British Virgin Islands truly begins.

In the afternoon, we'll set sail to nearby Norman Island, a haven for relaxation and adventure. Drop anchor in the protected waters of The Bight, where you can enjoy a variety of activities. Snorkel at the famous Norman Island Caves, rumored to have inspired Treasure Island, or simply float and soak up the sun from the deck of your yacht.

As the sun dips low, enjoy a cocktail while your private chef prepares another memorable meal. Cap off your day with a stunning sunset view over the water and the option to visit the legendary Willy T, a floating bar known for its lively atmosphere.

Start your day with an early sail to The Baths, one of the British Virgin Islands' most iconic and enchanting destinations. While you rest or savor a quiet morning coffee, your crew will guide the yacht to this natural wonder. Arriving early ensures you can explore the magical granite boulders, tidal pools, and grottoes in serene solitude before the crowds. Wander the famous caves trail, capturing unforgettable photos along the way. Afterward, return to your yacht for a refreshing breakfast prepared by your chef.

Next, sail up the Sir Francis Drake Channel to George Dog, one of the idyllic islands in the Dogs. Here, you can spend your late morning snorkeling vibrant reefs, sunbathing on deck, or simply floating in the crystal-clear water. It's the perfect way to unwind before enjoying a delicious lunch back on board.

In the afternoon, you'll continue on to the famed North Sound, celebrated as one of the Caribbean's most beautiful natural harbors. To escape the busier areas, your crew will anchor in nearby Eustatia Sound—a peaceful retreat within easy reach of all the action.

The rest of your day is filled with choices: snorkel the vibrant Eustatia Reef, where you might spot an old cannon nestled within the reef—a fascinating relic of the past. Walk the pristine sands of Prickly Pear Island, or take a short tender ride to the iconic Bitter End Yacht Club for boutique shopping and waterside lounging. As evening approaches, head to Saba Rock for a magical sunset and the enchanting tarpon feeding. A visit to Leverick Bay is another great option.

Begin your day with fishing lines in the water as you leave the North Sound, enjoying a scenic downwind sail along the northern coastline of Tortola. Midday, your crew will anchor at the breathtaking Guana Island. While the eco-resort remains private, you can relax on the pristine white sands of White Bay or explore the serene Muskmelon Bay just to the north, known for its vibrant marine life and excellent snorkeling opportunities.

After a leisurely lunch and some time to unwind, continue cruising the picturesque north shore of Tortola before settling in for the evening at Brewers Bay. This lesser-visited gem offers a tranquil anchorage and a pristine beach perfect for swimming, floating, or simply soaking in the island's beauty. As the sun sets, cocktails and another delicious dinner await, with the option of ending your evening watching a movie under the stars on your yacht's projector.

Sail to the iconic Jost Van Dyke, an island rich in history and surrounded by breathtaking natural beauty. Begin the day by anchoring near Sandy Spit, a picture-perfect islet with soft white sand and crystal-clear waters. This tiny island is an idyllic spot for sunbathing, enjoying a picnic, or simply soaking in the serene 360-degree views.

Make the day your own with activities tailored to your group's preferences. Sample the Soggy Dollar Bar's famous concoction - the Painkiller at the lively White Bay. Take a hike from Foxy's Taboo to the Bubbly Pool, a unique sea-fed pool that's as refreshing as it is fun. Alternatively, visit nearby Sandy Cay, known for its pristine beach and short hiking trail through lush greenery. Whether lounging aboard, swimming, or making use of your yacht's water toys, the beauty and charm of Jost Van Dyke promise an unforgettable experience.

Start your day with a leisurely morning as your crew prepares the yacht for another spectacular day. Your first destination is The Indians, a breathtaking group of rocky islets renowned for offering some of the best snorkeling in the BVIs. Dive into the crystal-clear waters and marvel at the vibrant coral reefs and marine life that call these unique formations home.

After your underwater adventure, we'll set sail for Peter Island's Little Harbour, a serene and secluded anchorage. Your yacht will be secured with a stern tie just feet from the shoreline, creating the perfect setting for a relaxing afternoon. Lounge on deck, swim in the turquoise waters, or simply float and soak in the peaceful surroundings.

As the day winds down, enjoy cocktails and a gourmet dinner prepared by your private chef. Cap off the evening with a breathtaking sunset over the calm waters—a picture-perfect way to savor your final night in the BVIs.

After clearing customs as you return to the U.S. Virgin Islands, your yacht will sail towards St. John for a final morning of island exploration. Choose from Waterlemon Cay or Hawksnest Bay, where you can snorkel vibrant coral reefs, hike scenic trails, or simply relax on the sandy shores.

Following lunch aboard, the adventure continues offshore to Buck Island, part of the National Wildlife Refuge. This pristine island offers clear waters for snorkeling and swimming, with opportunities to spot sea turtles, tropical fish, and colorful coral reefs. Onshore, enjoy short walks and take in stunning views of the surrounding sea. Buck Island provides a perfect mix of tranquility and adventure to close your Caribbean journey.

For a final evening in the islands, head to Christmas Cove where you'll celebrate with cocktails and another fantastic sunset.

Your final morning in the Virgin Islands begins with a serene start aboard your yacht. Relish a leisurely breakfast as you take in the breathtaking turquoise waters one last time. It's the perfect moment to reflect on your unforgettable journey through the islands.

Your crew will set sail back to the marina, ensuring a smooth and timely arrival for your noon departure. Once ashore, your transportation—whether to the airport or other accomodations—will be seamlessly handled. As you bid farewell, take with you memories of an extraordinary adventure and dreams of returning to this Caribbean paradise.