The Virgin Islands, taken together, form the largest archipelago in the Caribbean, with approximately 90 islands and inlets scattered from Virgin Gorda to Puerto Rico—an expanse we intend to explore. This uncommon 14-day itinerary is focused on adventure sailing and passage-making. While not a formal sailing school course, we encourage sailors to participate and sail as a team. This voyage is a once-a-year departure and limited to just five cabins. Don’t miss out—connect with a Sailing Collective Travel Coordinator today to book your cabin!
Cost breakdown: $590 per day including captain & chf + provisioning + onboard meals
Total Distance: ~260 NM This itinerary brings together the spirit of voyaging with leisure and the spirit of the Virgin Islands diverse islands. Over the 14-day voyage, we explore the stretch of islands from British, US, and Spanish circumnavigating the largest archipleago in the Caribbean. Approximate itinerary:
Board your yacht at 7:00 PM at Hodges Creek Marina on Tortola. Settle in, stow provisions, review the safety briefing, and enjoy your first Caribbean evening dockside. Dine aboard or at the marina restaurant. Early to bed for an early start.
Cast off by 9:00 AM for a beautiful sail up the Sir Francis Drake Channel. Stop midday to explore The Baths—giant granite boulders, secret grottoes, and warm turquoise waters. Continue to North Sound and anchor near Leverick Bay or Prickly Pear for the night.
An early morning departure takes you north to the flat, coral island of Anegada. Navigate through the reef and anchor at Setting Point. Rent scooters to explore Loblolly Bay, Cow Wreck Beach, and enjoy Anegada’s signature grilled lobster at sunset.
A longer sail westward today to the charming island of Jost Van Dyke. Arrive mid-afternoon in White Bay for a swim and a drink at the Soggy Dollar Bar. Then shift to Great Harbour for the night and check out Foxy’s famous beach bar.
Sail to Cruz Bay, St. John, to clear into U.S. waters. Enjoy a walk around town or top off supplies. Then head to Maho or Francis Bay for a peaceful mooring and some of the best turtle snorkeling in the Virgin Islands.
Free-day to explore St. John with excursions inland and celebrations ashore.
Spend the day exploring Culebra. Visit the stunning Flamenco Beach, snorkel at Tamarindo or Carlos Rosario, and relax at anchor. Overnight in Ensenada Honda or the calm, reef-protected Dakity anchorage.
Sail south to the wild island of Vieques. Anchor off Esperanza’s colorful waterfront. Stroll the Malecón, dine ashore, and cap off the evening with a guided kayak tour of bioluminescent Mosquito Bay—unforgettable.
Cruise east along Vieques’ southern coast. Anchor off Playa La Chiva or Caracas Beach for swimming, snorkeling, and solitude. Enjoy a quiet dinner on board or return to Esperanza for one more evening in town.
Depart early for a beam reach across to St. Croix. Drop anchor near Christiansted and explore the historic town with its Danish colonial charm, boardwalk bars, and coral-stone buildings. Try some local cuisine ashore.
Sail to Buck Island National Monument for hiking, beach lounging, and snorkeling the famous underwater trail. Return to Christiansted or Green Cay for your last night in St. Croix waters.
Sail north to Norman Island, back in the BVIs. Anchor in The Bight and enjoy snorkeling at the caves or a celebratory dinner on the floating bar Willy T. A perfect spot for your final night aVit anchor.
Weigh anchor early for a short sail back to Hodges Creek. Arrive by 10:00 AM to fuel up, check in, and complete your full-circle exploration of the Virgin Islands.
The day-to-day itinerary will vary with long days next to shorter days. A full day of sailing could be as much as 10-hours or as little as 2-hours. The goal is to sail as much as possible while still having time to explore the islands and enjoy the experience.
It would be recommended to have some sailing background - it is a two-week voyage. There will be leisurely aspects and there will be more intense aspects as well. This voyage is suited best for a sailing lover eager to gain more cruising experience and settle into life at sea.
Yes, there will be a chef preparing meals. Keep in mind, during long passages where the boat is heeling over, meals might be more simple. If you are looking for the classic "Sailing Collective" voyage with delicately plated meals, consider joining our one-week catamaran charters. Meals will be delicious while aboard, at times, however, will be more suitable for this style of voyage.
There are two options: 1) Fly into Beef Island, Tortola. There are direct flights from Miami, St Thomas, and San Juan in Puerto Rico. 2) Fly into St Thomas and take a 60-minute ferry to Tortola. If you fly into St Thomas, be sure to coordinate your arrival time with the ferry schedule. The last ferry ends bewteen 4:30 - 5:30pm depending on the day.
Not necessarily, we can convert two of the aft-cabins into a double cabin. Connect with the SC Travel Team if you would like to book a double cabin.
Your captain & chef or first mate • All provisioning for onboard meals • mooring fees • Boat water & fuel
Travel • Spirits & wine • Land activities like dining ashore • Marina stays • Customs & immigration • Crew gratuity (10% - 20% of your ticket price)
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