Sailing the British Virgin Islands

The British Virgin Islands (BVIs) lie east of the US Virgin Islands, which collectively make up the northern terminus of the Lesser Antilles. A string of rocky islands, centered on the main island of Tortola, the BVIs include Jost Van Dyke to the northwest, Virgin Gorda to the southeast, the sandy coral island of Anegada to the northeast, and number of smaller islands scattered throughout. My wife and I, prior to our marriage, had decided to make our first vacation together as a couple a sailing vacation. We had met sailing in our youth, in fact she taught me how to sail nearly two decades ago, and we had reconnected later in life. We had stayed sailing on various boats separately and this would be our first time sailing together in some time. We had initially planned to sail in the Bahamas, but when hurricane Dorian devastated the Abacos, we went with the BVI’s instead.

I had obtained my USCG merchant mariner’s credentials as a master of vessels under 50 tons (Inland w/ sailing endorsement), so doing a bareboat charter wasn’t an issue. We wanted to go with one of the smaller, family-owned charter companies and we weren’t disappointed with Conch Charters out of Road Harbor in Tortola. We were monohull sailors and at the time I couldn’t afford one of the larger boats, so we settled on a Sun Odyssey 32 built by Jeanneau. They are lovely little boats: a great design with clean lines, nearly 500 SQFT of sail area on a masthead sloop rig, with just under 10,000 lbs displacement. She handled well, tacking on a dime with her fin keel, and the open transom proved to be perfect for swim call or getting on and off the boat in general. We became fans of the modern design quickly! For a charter boat though she’s tiny and we were without doubt the smallest cruiser in any of the anchorages we stayed in.

First day sailing from Tortola to Norman Island with St. John in the background

My sailing experience has been in the Chesapeake Bay, the coasts of Florida and one long passage from the Bahamas to Charleston, SC. I had never sailed in the Caribbean before and was unprepared for the beauty of it. As we sailed out of Road Harbor with the trade winds on our port quarter, the hills of Tortola behind us, the island of St. John in the distance … it was a little overwhelming. I remember saying to Dana over and over again, “Can you believe we’re here, can you believe we’re doing this?”

Our plan had been to sail round Tortola, visiting as many islands as we could, but the lady at Conch Charters offered better advice. She reminded us that we were on vacation and that chilling out on the islands might be a better option. I’m glad we took her advice. We sailed southwest down the Drake Passage, so named for Sir Francis Drake who first charted it, toward Norman Island. I’d read experiences of a bar there called Willy T’s, that was supposed to be one of the places to see in the BVI’s. The bar was cool, a two-decked barge in the middle of the anchorage, but had a bro-vibe that we didn’t really need. The anchorage though was lovely and as we watched the sunset that first night, the stress seemed to fall away.

There was one point when we first sailed from Tortola where I started to explain to Dana how we would tack through the eye of the wind and she looked at me calmly and asked, “And who taught you how to do this?” ... I have never tried to silently study the wind and the waves more intently in my entire life. We sailed northeast from there up the Drake Passage to Cooper Island, which offered great snorkeling. I should state here that I don’t swim, I float directionally, so I am not comfortable in the water. Dana on the other hand is a mermaid and would be in the water the second we dropped anchor or tied up to a mooring ball.

From Cooper Island we sailed up to the northern part of Virgin Gorda to Leverick Bay, which we stayed at for two days so we could explore. This small bay is part of the north sound, known as Gorda Sound, which is enclosed by several small islands, including Sir Richard Branson’s Nechar Island. We used a taxi service run by a lovely woman named Patsy to visit some historic ruins, the famous Hog Heaven Bar, and the Baths.

View from Hog Heaven Bar

We had drinks and lunch at the Hog Heaven Bar and the view was worth it. We could see the whole of Leverick Bay, including our little boat in the anchorage. The Bath’s are a famous tourist destination and worth the trip, though we were unfortunate in our timing: a cruise ship was in port and had dropped off a ship-load of tourists as we arrived. We had to stand in line, but the boulders, beach, …etc. were all pretty cool. One of the places Patsy showed us that I wish we could have anchored in was Savanna Bay on the western side of the narrow isthmus of Virgin Gorda. It was one of the few no-go areas for charter boats because of coral heads and a tricky entrance, but it would have been so nice …

Afterward, we made it to the bar in Leverick Bay, where we were talking with some Canadian sailors who were sailing on their own boat. They found out we were Americans and asked if we were going to have any trouble getting back into the US? We were confused and then they told us about the global pandemic and that borders were rumored to be shutting down soon. I should have mentioned at the beginning that we took this trip in March of 2020. We had turned our phones off at the beginning of the trip and now, four days in, had no idea what was going on in the world. Over Rum Runners and Pain Killers, we talked about it and Dana and I decided to stay on the vacation. After all, we were on a boat, if we were stuck somewhere, on a boat in the BVI’s wasn’t the worst place.

We spent three more days sailing around the BVI’s and loved it, though I would avoid Trellis Bay in the future. One part I did find amusing was when we sailed into Deadman's Bay, which is adjacent to Dead Chest Island. The site notorious for a probably fictitious marooning by Blackbeard of his crew in the 18th century. Deadman’s Bay and Dead Chest Island would be the genesis of Robert Louis Stevens song, “Fifteen men on a Dead Man’s Chest.” The island and bay also reminded me of a line from Pirates of the Caribbean:

Gibbs: “It’s not for naught it’s called Shipwreck Island where lies Shipwreck Cove in the town of Shipwreck.”

Jack: “You know, for all that pirates are clever cobs, we are an unimaginative lot when it comes to naming things.”

In the end, despite the pandemic, we were able to complete our charter and catch a ferry to St. Thomas for our flight home. Unbeknownst to us, it was the last flight out of St. Thomas before the world shut down. It would also be the last sailing trip for awhile, but it cemented the idea in our minds that our future together definitely involved sailing.

Deadman's Bay near Dead Chest Island