The Virgin Islands have long been a sailor’s dream due to its many islands, protected bays, prevailing winds and crystal-clear waters that are mostly calm. Sailing the Virgin Islands on your own charter boat is one of the best ways to experience the region’s natural beauty and alluring islands.
Chartering and sailing the Virgin Islands
I’ve had the luck to sail the Virgin Islands three times, not because I’m an experienced sailor but because I know people who are. One of the best reasons to charter a boat is that it lets you be the boss of your own itinerary (well, the weather is the ultimate boss, but you get what I mean). Furthermore, chartering your own boat can be more affordable than you might think. In fact, it can cost less than a cruise ship, especially when you add cruise extras like balcony rooms, offshore excursions and onboard alcoholic drinks. Of course, how much you spend on a charter boat depends on your own circumstances. A bareboat with your own sailing crew is cheapest, but for sailor wannabes with limited experience, there are also options like adding a skipper or even a hired crew to do the cooking and sailing. There are also sailboats of all sizes and price categories. There are even motor yachts, but as someone who grew up in a sailing family, I’m not going to talk about those.
The main charter season is from November through July, making now the best time to think about the next season (the hurricane season is from late July to early October).
Because you can quickly sail from one mooring to the next, there are many options for traveling between St. Thomas in the US Virgin Islands up the Sir Francis Drake Channel to Virgin Gorda in the British Virgin Islands. Most charters last seven days, allowing ample time to explore islands along the way. Being on your own boat allows you to be self sufficient (just make sure you bring enough provisions with you, as well as cash, as some establishments aren’t equipped to accept credit cards). Although charter companies can provide you with recommended itineraries and a list of establishments, below are my own personal favorites of places to overnight and play when sailing the Virgin Islands.
St. John’s Island
St. John’s is one of the Virgin Islands’ prettiest, not the least because two thirds of it is a national park. I’d spent a couple of vacations more than 25 years ago at Maho Bay campground (I even spent my honeymoon there), which has sadly closed. Maho Bay does, however, offer great scenic views of wooded hills. However, I find Leinster Bay even more spectacular and pristine, with the ruins of an old sugar mill and a long-abandoned stone building the only visible remainders of human intrusion.
Soper’s Hole, Tortola
If you’re sailing between the US and British Virgin Islands, you’ll go through customs at Soper’s Hole, which is a colorful village consisting of a handful of shops, a couple of restaurants on the waterfront and grocery stores for stocking up on provisions like fresh produce, beer, ice and other necessities. In other words, it’s a natural for lunch.
The Bight, Norman Island
This is the party place of a sailing adventure along the Sir Francis Drake Channel, due to the floating barge Willie T, formally known as the William Thornton. It’s infamous for drunken revelry, attracting charter folk and Tortolans who boat over for the evening. I distinctly remember an evening here of drinking and dancing, after which one member of our own crew fell off the dock. I’m sure he wasn’t the first.
On shore is Pirates Bight, a great place to spend a lazy afternoon. It offers a pretty beach, food ranging from chicken tenders and barbecued ribs to pasta, burgers, and seafood, plus cocktails and beer. I once surprised my then-teenaged sons by timing our trip just so we could land here to watch the World Cup, which my soccer fanatics had resigned themselves to missing. They declared the next morning’s snorkeling, on the other hand, the best they had ever experienced. Given a choice, I think they would have chosen snorkeling.
The Pelican and Indians
If you leave your mooring at The Bight early, you can motor over to the Pelican and Indians, nearby jagged rocks sticking up out of the water, to secure a mooring and eat breakfast. This is one of the best snorkeling spots I’ve ever seen, with vertical rocks filled with all kinds of coral and teeming with fish.
The Baths
Located on the southern end of Virgin Gorda, this is the star attraction on a sailing trip through the Virgins (and is understandably also crowded). It’s a natural playground of huge and smooth granite boulders piled up along the coast, tunnels, caves, clear ponds and hiking trails. It takes some scrambling and crouching to work your way through this rock maze, but it’s worth it. For kids, this is a highlight. That night, we moored at the Bitter End Yacht Club, put on our fanciest clothes (well, we didn’t have anything considered really fancy, but they were clean) and enjoyed an upscale dinner.
Salt Island
This is a quirky, quick stop. It has a natural inland salt pond and was therefore useful to early settlers and sailors. Two friends on one of my sailing trips remembered stopping by some years back and buying salt from an old guy living on Salt Island. He wore a hard hat, apparently after a coconut dropped on his head.
Peter Island
Of all the islands where we spent the night sailing the Virgin Islands, this is my favorite. I’ve stayed at two places: Key Bay and Little Harbour. Both offer decent snorkeling and are small, with room for only a few other boats, and are free of resorts or development. We were lucky to have both alone to ourselves for much of the afternoon, and because they’re so pristine, it was easy to fantasize that we’d come across your own Treasure Island. For me, it was the epitome of what sailing is all about. Away from the world. Reading a book or just contemplating. Swimming and snorkeling at leisure. Watching the sun set or gazing at an incredibly clear Milky Way. Sleeping to the gentle rocking of waves lapping the side of the boat. It doesn’t get any better than that.
