Day 1 – Unpack, settle in and cast off from Road Town, Tortola around noon on your Caribbean sailing charter. It’s an easy reach to Deadman’s Bay on Peter Island. Jump in and swim or dinghy ashore to the beautiful sandy beach before lunch. Then motor around the point to Little Harbor or isolated Great Harbor for the night.

Day 2 – On day two, set sail towards Beef Island up the Sir Francis Drake Channel. Anchor at Marina Cay and go ashore to visit the famous Pusser’s restaurant and store. Relax with a drink and dinner on the island. Or anchor in Trellis Bay – protected by a reef guaranteeing fantastic snorkeling. You’ll find rustic English-style dining and entertainment on tiny Bellamy Cay.

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Day 3 – Sail east to Virgin Gorda and make a lunch stop at The Baths. Dive into crystal waters washing colorful reefs beside boulder-formed caves. Pick up a mooring ball for the day and dinghy, swim or snorkel ashore for a breathtaking tour as you wade through sandy pools and caves. Don’t forget your camera!

A north swell prevents you from overnight anchoring here, so you’ll want to motor around to Spanish Town. Anchor outside the marina entrance, or go in and tie up for the night. You’ll find fuel, ice, water, groceries and West Indian entertainment at nearby bars and restaurants.

Day 4 – A balmy downwind sail takes you to Monkey Point on Guana Island where you’ll find spectacular snorkeling on the southern end of the island. It’s a great day anchorage.
After lunch, continue west to Cane Garden Bay on northern Tortola, famous for picture-postcard beauty and full moon parties. Dinghy ashore from your for ice, supplies, mini-markets and fun beach bars with steel-drum bands. This is a secure overnight anchorage in all but a strong northerly. Sample genuine cane rum from the Callwood Distillery.

Day 5 – Day five of your Caribbean sailing charter takes you to beautiful Sandy Cay whose name speaks for itself. You can swim, snorkel, kayak, or hike around the tiny sugar-white sandy island.

Then head into Great Harbor on Jost Van Dyke for the night. Discover great little local shops, restaurants and bars including the famous Foxy’s Tamarind Bar and Grill serving excellent dinners on Thursday evenings. Make reservations! Ice and some groceries are available. BVI Customs & Immigration offices are here also.

Day 6 –It’s a long, leisurely sail to Norman Island. Robert Louis Stevenson wrote “Treasure Island” after visiting here. Steeped in history and legends of pirates and buried treasure, some found as recently as 1969! “The Bight” is a great overnight anchorage. Enjoy some lively entertainment aboard the Willy T (a tall ship restaurant named after William Thornton, architect of the U.S. Capital Building.)

Day 7 – Dinghy or kayak ashore to snorkel the Caves, populated with breathtaking arrays of colorful tropical fish. Snorkel or dive at the Indians, a group of sharp peaks rising from the sea about a mile offshore before returning to Tortola.

Other Suggested Caribbean Sailing Charter Anchorages:

Hawksnest Bay, St. John – Pick up a National Park mooring ball and swim or dinghy ashore to a beautiful white sand beach. You can hail a taxi to Cruz Bay for some shopping or nightlife. The mooring is free for the day, but there is a charge to stay overnight.	Leinster Bay, St. John – Towards the east end of St. John on the north coast, snorkeling around Waterlemon Cay is about the best you will find anywhere in the islands. You’ll find colorful parrotfish and schools of other reef fish. Ashore you’ll find a trail to the ruins of a centuries-old Sugar Mill. This well protected anchorage is a great spot for kayaking and an evening BBQ aboard.	Coral Bay, St. John – A great hurricane hole to explore by dinghy before making your way ashore to Skinny Legs or one of the other bars and restaurants for some island culture.
Lameshur Bay, St. John – Like to hike? Guided park excursions provide opportunities to explore trails ranging from easy walks on well-maintained paths to difficult climbs along brushy tracks. Excellent for bird-watchers.	Water Island, St. Thomas – Water, ice and restaurants found here. Cruise along the south coasts of St. John and St. Thomas, then head into protected waters of Honeymoon Bay to the west of Water Island. Swim from a beautiful white sand beach, explore ashore or dinghy to Frenchtown for duty free shopping.	Christmas Cove, Great St. James – Great lunchtime or overnight stop for snorkeling at this beautiful well-protected anchorage.
Benner Bay, St. Thomas – Home of VIP Yacht Charters. Restock ice, fuel, water and provisioning.	Trunk Bay, Cinnamon Bay, Francis Bay, St. John – Absolutely breathtakingly beautiful anchorages, all part of the USVI National Park, and within easy reach from St. Thomas. Mooring balls are free for the day but have a charge for overnight. Hail a taxi along the road behind the beaches for a shopping excursion to Cruz Bay.	Soper’s Hole, Tortola – Find water, ice, supplies, restaurants, shopping, and a full service marina offering slips with water, electricity and a well-stocked market. If coming from the USVI, clear customs & immigration before your visit ashore. Take a slip at the marina or pick up a mooring ball. It’s too deep to anchor.
Little Harbor, Jost Van Dyke – Great overnight anchorage.	White Bay, Jost Van Dyke – A beautiful white sand beach, ideal for a lunch stop. Very small, shallow anchorage surrounded by reefs that can be tricky in a sailboat. Home of the famous Soggy Dollar Bar where the legendary rum-based “Painkillers” originated.	The Dogs – Great Dog, George Dog, West Dog & Seal Dog. All protected National Trust islands, the snorkeling and diving here is fantastic.
North Sound, Virgin Gorda – Take a walk around the luxury resorts of the Bitter End Yacht Club or Biras Creek Hotel. Loaded with amenities, including restaurants and shopping, plus fuel, ice, water and groceries.	Anegada – Start early and sail from Virgin Gorda to Anegada for the famed lobster of the Anegada Reef Hotel. A limestone island, Anegada has claimed over 300 wrecks so snorkeling is superior. Go only in perfect conditions. Fishermen can try bonefishing on the flats.	Cooper Island – Water, ice, bar & restaurant. Barbecue aboard or dine ashore for lunch or dinner at the Cooper Island Beach Club.
Salt Island– In earlier days, salt was harvested here from three evaporating ponds. On the west coast is the final resting place of the HMS Rhone, taken in 1912 by a hurricane, and now reputedly the best wreck dive in the western hemisphere. Great lunch stop.	Peter Island –Peter Island Resort & Yacht Harbor offers 20 slips, if you wish to tie up for a fee.	Lameshur Bay, St. John – An idyllic anchorage on the southeast coast of St. John. Wonderfully secluded with great snorkeling.
Caneel Bay, St. John – Beautiful Caneel Bay has a luxury resort that includes fine dining. This is a good daytime anchorage for your Caribbean sailing charter, but overnight at Hawksnest Bay, which offers better protection.	Cruz Bay, St. John – Head ashore to clear customs, shop and visit the village. Best to anchor at Hawksnest or Caneel Bay and dinghy in, as Cruz Bay’s anchorage is quite crowded and has a constant flow of ferry traffic.

Sample Itineraries: