Caribbean Yacht Charters

A Caribbean Crewed Yacht Vacation can be broken into three sailing areas, the Virgin Islands, the Leeward or northern-most islands and the Windward or southern islands.  Each of these sailing areas offers a variety of cultural and natural experiences.

Sample Itinerary

7 Days in the Caribbean

Pick up at Trellis Bay, Caribbean

Day 1:  Fly into Beef Island, Caribbean where your crew will meet you at nearby Trellis Bay.  You’ll be taken aboard your yacht, shown around and settled in with a Caribbean cocktail.  Take some time to get acquainted with  the crew and go over your expectations for the trip.  Then begin your adventure  with a sail to Spanish Town.

Day 2:  Following an early breakfast on your yacht in the Caribbean, sail to the southern tip of Virgin Gorda where you’ll find the Baths.  The Baths are a true wonder of nature in the caribbean.  Huge boulders are strewn about the harbour as though thrown around by some ancient Colossus. The formations have created caves, walkways, and crystal clear pools perfect  for a snorkeling adventure. Continue up the coast of Virgin Gourda to the North Sound. Here you can hone your windsurfing, waterskiing, or tubing skills.  The expanse of water here is well protected by reefs that not only ensure calm waters, but also provide fantastic snorkeling.  Celebrate your victories at the Bitter End resort over Pina Coladas.

Day 3:  Set sail for Anegada, Caribbean, where there is nothing but long miles of beach to walk, reefs to snorkel or dive, shipwrecks to explore and lobster to eat. Sailing is done in bright sunlight to pick out the unmarked coral heads that pop up as you approach the island.

Day: 4: Start south to Norman Island, Caribbean-- the inspiration for Robert Louis Stevenson’s Treasure Island.  Anchor up at Cayes Caves and spend the afternoon searching for Blackbeard’s treasure.  Then sail around the corner to the Blight where you can have a quiet dinner on your yacht, or continue the skullduggery on The William Thornton (Willy T’s) – an old Baltic Trader that’s been converted into a floating bar and restaurant.

Day 5: No trip to the Virgin Islands is complete without a stop at Jost Van Dyke. Sail to White Bay and swim ashore to the Soggy Dollar Bar to trade in your wet duckets for a Painkiller or two.  Then continue around to Great Harbour, home of the legendary Foxy’s. Most days Foxy himself is on hand playing Calypso songs  detailing life on the Islands.  If you’ve got the energy, continue on to Little Harbour, Caribbean, where you’ll find the nightlife in full swing at Sidney’s and Harris’s Place.

Day 6: Shake the cobwebs from the night before away over a leisurely breakfast then sail along Tortola.  Stop at Guana Island for a relaxing day on the beach at Monkey Bay or head back to Tortola to explore Road Town, the island’s main port. Watch the sunset from Sky World atop the island’s highest peak before sampling the local cuisine at one of the many restaurants.

Day 7: Sail back to Trellis Bay for one final swim, then it’s back to the airport and real life.