Caribbean Sailing Vacations by Ed Hamilton

The Virgin Islands.

The Virgin Islands are the most popular charter destination for good reason. A relatively small cruising ground with a huge variety of beautiful bays and beaches, great snorkelling/diving, lovely scenery and some excellent beach bars and entertainment ashore.
Hard to beat for a bareboat or crewed charter, unless you want longer sails or less people. A particularly good choice for a first time charter. The outside islands protect the area from the Atlantic swells without stopping the breeze, providing great sailing and comfortable powerboating. The climate is close to perfect. The cruising ground is primarily in The British Virgins, but charters can start in the more heavily populated U.S.V.I. The hurricane season peaks between mid August and late October.

7 Night Suggested Itinerary
click on links, pictures or maps for more info.

Day 1:
Most charters start around noon in Road Town,
It's a leisurely beam reach across to Peter Island. Spend the afternoon in Deadman's Bay, famous for its spectacular beach.
Move to nearby Great Harbor for the night. There is a restaurant/bar for those wishing to eat ashore and luxurious Peter Island Yacht Club in the next bay for a more formal experience.

Day 2:
Sail east to
Cooper Island, enjoying the beach, snorkelling and the Cooper Island Beach Club.
In the afternoon, sail on to Trellis Bay (or just stay at Cooper Is) and enjoy The Last Resort and other attractions in this protected bay. Alternatively, nearby Marina Cay offers great snorkelling, a fun bar and a popular restaurant.
Day 3:
Start early to beat the rush and sail across to The Baths on
Virgin Gorda. This popular spot features huge boulders, some covering a small pool, great snorkelling and normally plenty of people! Sail up the coast, perhaps stopping at beautiful Savannah Bay for lunch, to The Bitter End Yacht Club, but make sure you leave enough time to enter North Sound in good light. The Bitter End is a large resort with a bit of everything, including small boats to rent and race, an excellent restaurant and bar and some great hiking trails nearby.
Day 4:
It's perfectly possible to spend two nights in North Sound, but those that want to keep sailing head north to
Anegada. Unlike the rest of the BVI, the highest point of this large island is only 28 feet and you are over the reef before you can see the island, so it is essential to only do this 20 mile trip in good weather and good light. Leave the Bitter End before 9:00 to do this. Some bareboat companies make Anegada off limits unless escorted, but those that make the trip can enjoy miles of relatively people free beaches and some fun night life.
Day 5:
From Anegada or North Sound, it's a great broad reach or run to Cane Garden Bay,
Tortola. This is one of the most spectacular beaches in the area. It is also home to several popular bars, some of which feature steel bands and other live music. Great local night life but if there is a stong winter swell running you might want to move to Jost Van Dyke for the night.
Day 6:
After a leisurely breakfast, sail across to
Jost Van Dyke, stopping perhaps at Sandy Cay for a swim and lunch. There are three main bays to choose from on Jost. Beautiful White Bay has the popular Soggy Dollar Bar, home of the 'Painkiller'. The main village is in Great Harbour, along with the imfamous Foxy's. Little Harbour has two restaurants/bars, Sidney's Peace and Love, and Harris's Place.
Day 7:
Head south, past Soper's Hole, to
Norman Is. Explore the caves and the fabulous snorkelling. In the evening the thicker skinned party goers will enjoy the 'Willie T'. The Pirate's Bight is another option.
Day 8:
Sail across the Drakes Channel in time for a noon departure in Road Town and lunch at one of the many restaurants before flying home. For charters over 7 nights or for guests who really want to shop, you can incorporate a trip to
St. Thomas and St. John in the US Virgin Islands. If 7 days sailing is your max, you can miss Anegada and take a day ferry from West End Tortola to downtown Charlotte Amalie in St. Thomas, or start/finish the charter in the USVI or stay one day there at the end of your trip. The ferry takes about 45 minutes.
Let's start by asking you some questions and emailing you some boat and company suggestions.
Websites for crewed yachts based in The Caribbean:
Catamarans Powerboats

When you book your Virgin Island charter through us, we include a copy of the VI Cruising Guide, even though some bareboat companies no longer do this and simply link to pdfs. Take a look at a slick online sample of the guide, or purchase a copy.

This itinerary is just a sample. There are many different variations/possibilities/starting ports depending on the things you enjoy, so be sure to ask one of our agents for suggestions and first hand advice.

Cruising ground questions? Send us an email

Ask us to suggest some suitable boats and crews