Thinking about taking a holiday with a St. Thomas catamaran charter or a St. Thomas sailing yacht charter? Look no further than our complete yacht charter guide that has everything you need to know about your next USVI sailing holiday.
Sailing conditions in the U.S. Virgin Islands are typically at their best from mid-December through late April, when the Christmas Winds ease into steady trade winds of around 15–20 knots and rainfall is minimal. Hurricanes and tropical storms generally pose the highest risk between June and November, making early winter to spring the most popular window for chartering. During these months, you can enjoy warm, sunny days, clear waters, and calmer seas—perfect for island-hopping around St. Thomas, St. John, and St. Croix.
What are the sailing qualification and license requirements to charter a yacht or catamaran in the USVI? In the U.S. Virgin Islands, a formal sailing license is not always mandatory for bareboat charters, though some charter companies prefer that you hold an ASA (American Sailing Association) or RYA qualification for insurance purposes. More often, your sailing resume—outlining coastal navigation abilities, anchoring proficiency, and boat-handling experience—will determine approval. Because the USVI’s waters feature relatively consistent trade winds and numerous protected bays, charterers can find conditions suitable for a wide range of skill levels. However, it is wise to brush up on local maritime regulations and best practices around coral reefs to ensure a safe, environmentally conscious journey.
The U.S. Virgin Islands blend American, Caribbean, and African cultural influences, reflected in lively music festivals and colorful architecture. Stop at beach bars and local eateries to indulge in fresh mahi-mahi, conch fritters, and spicy Caribbean curries. St. Thomas’s Charlotte Amalie is known for duty-free shopping and restaurants serving barbecue with island flair, while St. John’s laid-back vibe highlights the natural beauty of its national park. Listen for local calypso tunes or steel drum performances that underscore the islands’ vibrant cultural heritage—perfect for those seeking a relaxed yet flavorful USVI sailing vacation.
All yachts arriving from outside the U.S. customs zone must clear immigration at authorized ports. Harbor fees may apply, and certain national parks—like those around St. John—implement mooring-only policies to protect coral reefs. Always have your vessel’s registration and travel documentation at the ready; rangers or patrol officers may verify compliance. By respecting these straightforward rules, you’ll enjoy a carefree, regulation-friendly sailing escape through the U.S. Virgin Islands.
Each year, discerning sailors and luxury travellers flock to the U.S. Virgin Islands—St. Thomas, St. Croix, St. John and Water Island—to experience 117 miles of pristine coastline.
Renowned for powder-white beaches and kaleidoscopic coral reefs, the USVI combine tropical elegance with effortless onboard adventure, making them a perennial favourite for bespoke sailing vacations.
Your journey commences at Compass Point Marina on St. Thomas, easily reached via Cyril E. King Airport (STT). Direct flights operate from major U.S. hubs—Miami, Fort Lauderdale and Atlanta—while additional connections arrive through San Juan, Puerto Rico. Leading carriers serving the USVI include American Airlines, Delta Air Lines, United Airlines and others.
Once on island, reliable ferry links connect St. Thomas with neighbouring isles on frequent, budget-friendly schedules. A private transfer or taxi from STT to Compass Point Marina takes approximately 25 minutes.
Essential Sailing Tips & Local Insights
Entry & Currency
As a U.S. territory, the USVI allows American citizens to travel without a passport, though you must present proof of citizenship—such as a raised-seal birth certificate and government-issued photo ID—when departing. Many find it simpler to carry a valid passport. International visitors should ensure they have a passport from their home country. All transactions are conducted in U.S. dollars (USD).
Marinas, Moorings & Anchorage
St. Thomas and St. Croix host full-service marinas, while St. John relies exclusively on anchorages and mooring buoys. Within Virgin Islands National Park waters, the National Park Service maintains 210 public moorings, with an additional 45 administered by the Reef Ecology Foundation. These moorings are complimentary but typically closed to overnight use, so review any seasonal or time-of-day restrictions and associated fees in advance. Popular overnight anchorages include Caneel Bay, Francis Bay and Maho Bay—note that recreational anchoring is limited to 14 days per 12-month period. For extended stays, you may apply for a one-month long-term anchoring permit in designated zones.
Provisioning & Concierge Service
For self-provisioning, Pueblo Supermarkets—serving the USVI for over 50 years—operates two outlets each on St. Thomas and St. Croix, offering groceries, fresh produce and specialty items. Alternatively, let Yacht4Less handle your provisioning: we’ll stock your yacht to your exact specifications so that you step aboard with everything in place.
Day 1: St. Thomas – Caneel Bay & Maho Bay, St. John
Begin your Caribbean escape with a relaxed sail to the northern coast of St. John, anchoring first in Caneel Bay for snorkelling in calm waters. Continue to Maho Bay for the evening, where sea turtles, a sweeping white beach, and gentle tradewinds set the scene for an idyllic first night.
Day 2: Waterlemon Cay, St. John
Sail to Waterlemon Cay, one of the top snorkelling spots in the Virgin Islands, known for its thriving coral reefs and spotted eagle rays. Hike the Leinster Bay trail for stunning views and remnants of Danish colonial sugar plantations.
Day 3: Coral Bay, St. John
Cruise around to the eastern end of the island and anchor in Coral Bay, a bohemian enclave with rustic charm and untouched nature. Enjoy a laid-back evening at anchor with the option to go ashore for live music and local dining.
Day 4: Congo Cay, Carvel Rock, Mingo Cay – Magens Bay, St. Thomas
Explore the wild cays between St. Thomas and St. John, stopping to snorkel or dive at Carvel Rock’s dramatic underwater cliffs and Congo Cay’s reef-lined shores. Continue west to Magens Bay, one of the Caribbean’s most iconic beaches, and anchor in its calm, protected waters.
Day 5: Magens Bay, St. Thomas
Spend a full day enjoying Magens Bay, with options to paddleboard, kayak, or relax on the mile-long sandy beach. The bay’s scenic hills, warm waters, and sheltered anchorage make it perfect for slow, sun-soaked sailing days.
Day 6: Little St. James – Buck Island (St. Thomas)
Sail to the exclusive and uninhabited Little St. James for secluded snorkelling and reef exploration, followed by a stop at Buck Island. Here, you can swim among vibrant corals, sea turtles, and tropical fish in the protected marine park.
Day 7: Wreck of the Cartanza – Turtle Cove – Honeymoon Beach – Charlotte Amalie, St. Thomas
Spend your final day diving the Wreck of the Cartanza, snorkelling in Turtle Cove, or relaxing on Honeymoon Beach at Water Island. End your journey in Charlotte Amalie with a sunset drink overlooking the harbour and a final stroll through the historic capital’s cobbled streets.
Other Caribbean destinations
Sailing holidays in St. Martin
Sailing holidays in Guadeloupe
Sailing holidays in Martinique
