Sample Itineraries
Sample USVI Itinerary
Exploring the U.S. Virgin Islands aboard a sailing catamaran with the wind in your sails and turquoise waters stretching endlessly, the islands unfold like chapters in a Caribbean fairytale: St. Thomas pulses with harbor life and duty-free shopping, St. Croix invites you into its rich cultural mosaic, and St. John steals the show with its untouched beauty. From the powdery shores of Cinnamon Bay to the vibrant underwater world at Waterlemon Cay, and the rugged trails and secluded snorkeling at Little Lameshur, St. John alone offers a trifecta of unforgettable experiences. A catamaran lets you chase these moments with ease—snorkeling technicolor reefs by day, anchoring in quiet bays by dusk, and dining under a canopy of stars with the sea gently rocking beneath you.
Day 1) American Yacht Harbor → Cruz Bay, St. John
Begin your adventure from the bustling marina at American Yacht Harbor in Red Hook, St. Thomas. After a quick safety briefing, sail across Pillsbury Sound to Cruz Bay, the lively gateway to St. John. Dock or moor near the town and explore its charming boutiques, beach bars, and restaurants. It's the perfect blend of Caribbean flair and laid-back luxury.
Day 2) Cruz Bay → Maho Bay
Sail along St. John's north shore to Maho Bay, a tranquil stretch of white sand framed by lush hills. Known for its calm waters and sea turtle sightings, Maho is ideal for paddleboarding, snorkeling, and beach lounging. Don’t miss a visit to Maho Crossroads, a fun beach bar with live music and local eats.
Day 3) Maho Bay → Waterlemon Cay
Cruise east to Waterlemon Cay, one of the top snorkeling spots in the Virgin Islands National Park. Accessible by dinghy or a short swim, the cay is surrounded by vibrant coral reefs teeming with tropical fish, rays, and sea turtles. Hike the Leinster Bay Trail for panoramic views and a peek at the historic Annaberg Sugar Plantation ruins.
Day 4) Waterlemon Cay → Coral Bay
Sail around the eastern tip of St. John to Coral Bay, a quiet harbor with a bohemian vibe. This side of the island is less developed, offering a peaceful retreat. Visit the floating taco bar Lime Out, snorkel in Hurricane Hole’s mangroves, or explore the quirky shops and local eateries tucked into the hills.
Day 5) Coral Bay → Little Lameshur Bay
Head south to Little Lameshur Bay, a secluded gem with soft sand, calm turquoise waters, and excellent snorkeling. The bay is part of the Virgin Islands National Park and offers access to hiking trails like the Lameshur Bay Trail, which connects to the Reef Bay Trail and ancient petroglyphs. It’s a perfect mix of adventure and serenity.
Day 6) Little Lameshur → American Yacht Harbor
Sail back around the southern coast of St. John toward American Yacht Harbor, enjoying a relaxed downwind cruise. Stop for a swim or lunch en route at Salt Pond or Hansen Bay. Once docked, enjoy dinner at one of Red Hook’s waterfront restaurants and toast to a week well spent.
Sample BVI Itinerary
The British Virgin Islands (BVI) are a sailor’s dream and a snorkeler’s paradise, and there’s no better way to experience their magic than aboard a sailing catamaran. With over 60 islands and cays scattered across turquoise waters, each day brings a new adventure—from the legendary sea caves of Norman Island to the surreal granite formations and hidden pools of Virgin Gorda’s Baths.
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Beyond the breathtaking scenery, the BVI offer a celebration of island culture and laid-back luxury that’s best savored from the deck of your floating home. Sail into White Bay on Jost Van Dyke for a Painkiller cocktail at the iconic Soggy Dollar Bar, or moor at Cooper Island to sip craft rum as the sun melts into the sea. With beachside grills serving fresh lobster, barefoot beach bars buzzing with live music, and upscale restaurants tucked into lush hillsides, the culinary scene is as vibrant as the islands themselves.
Day 1) Nanny Cay Marina → Norman Island
Launch your journey from Nanny Cay Marina, a well-equipped hub on Tortola. Sail south to Norman Island, the legendary “Treasure Island” said to have inspired Robert Louis Stevenson. Drop anchor in The Bight, snorkel the famous sea caves, and enjoy a rum-soaked evening at the floating bar Willy T or dine ashore at Pirates Bight. It’s the perfect blend of mystery, marine life, and merriment.
Day 2) Norman Island → Cooper Island
Cruise northeast to Cooper Island, a small eco-conscious gem with turquoise waters and laid-back charm. Moor in Manchioneel Bay and snorkel at Cistern Point, where coral gardens teem with tropical fish. Ashore, the Cooper Island Beach Club offers a rum bar with over 300 varieties, a boutique, and sunset dining that feels like barefoot luxury.
Day 3) Cooper Island → Virgin Gorda
Sail to Virgin Gorda, home of the iconic Baths National Park. These massive granite boulders form natural pools and grottoes that are perfect for exploring and photography. After hiking through the Baths to Devil’s Bay, head to North Sound for upscale dining, watersports, and mooring options near Leverick Bay or Saba Rock. Virgin Gorda blends natural wonder with refined island charm.
Day 4) Virgin Gorda → Anegada
Day 5) Anegada → Scrub Island & Marina Cay
Sail south to Scrub Island, a luxurious private island resort with a full-service marina, spa, and dining. Just across the channel lies Marina Cay, a charming islet with a storied past and a breezy beach bar. Paddleboard, snorkel, or relax with a cocktail while soaking in panoramic views. This stop offers a perfect blend of indulgence and tranquility.
Day 6) Scrub Island → Jost Van Dyke
Cruise west to Jost Van Dyke, the “barefoot island” famous for its beach bars and festive spirit. Anchor in White Bay and swim ashore to the legendary Soggy Dollar Bar for a Painkiller cocktail. Explore Great Harbour for live music and local eats, or hike to the Bubbly Pool, a natural sea-foam jacuzzi. Jost is the ultimate celebration of island life.
