Sunday, November 30, 2025

British Virgin Islands sailing

We took another British Virgin Islands sailing trip with college friends. Returning from 2023 were me, Kathleen, Mick, Sue, John and Katy. New to the group were first-time sailors Tony and Lisa from the United Kingdom. Lisa and Sue ran track together at the University of Indiana, so the college connection remained, with another degree of separation. Like 2023, we chartered a four-cabin sailing catamaran through The Moorings out of Road Town, Tortola. See blog posts below from that trip. Read on for more about this voyage. 

BVI Travel Day      BVI Days 1-3       BVI Day 4        BVI Day 5-6       BVI Day 7

Unlike 2023, we were not living aboard Dragonfly, so our travel began from home rather than rural Mississippi. Also new this year is that the McSherrys are now Moorings yacht owners, so we saved on charter fees and received some added perks of ownership during our stay. 

Consisting of more than 60 islands, the BVI is a British Overseas Territory and part of the Lesser Antilles chain in the Caribbean. The term Virgin Islands is credited to Christopher Columbus, who visited here in 1493 on his second voyage to the New World. He claimed the archipelago for Spain and named it honor of Saint Ursula and the 11,000 Virgins, the fourth-century legend of martyred maidens killed in Cologne, Germany. The Arawak people lived here for more than 1,500 years and were displaced in the 15th century by the Caribs, for whom the Caribbean Sea is named. The Dutch were the first Europeans to settle the region (Spain claimed the islands by discovery but never colonized them), with the British taking control and establishing sugar plantations after the Third Anglo-Dutch War in 1672 and retaining influence ever since. Slavery was abolished on August 1, 1834, and is commemorated with an annual three-day holiday. 

Today’s BVI economy is driven by a combination of financial services and tourism. It is a major offshore financial center, with more than 700,000 registered companies, far exceeding its population of 35,000 residents, and is a leading hub for tax evasion and the concealment of assets. The islands are breathtaking, with an excellent blend of clear navigable waters, reliable winds, protected anchorages, and development to make it one of the most popular tourist and sailing destinations in the world. 

Thursday, Nov 13: This was a travel day and began with a 6:00 AM flight out of Minneapolis-St. Paul airport and a connection through Miami to the BVI airport on Beef Island. It was the last day of the U.S. government’s record-breaking, 43-day shutdown, so we were nervous about travel disruptions, which proved to be nonexistent. The rest of our group met in Miami and took an earlier flight to Beef Island, and when Kathleen and I boarded Mango Tango, our Leopard 45 sailing catamaran around 5:30 PM, the boat had been inventoried and most of the provisioning completed. We greeted our shipmates and the resident dock iguana, loaded our gear aboard, then had dinner at Charlie’s Restaurant on the charter base before sleeping aboard the boat. Map link: Roadtown, Tortola, BVI




Friday, Nov 14: We got a fairly early start in order to pickup snorkeling gear, final provisions and prepare for our 8:00 AM checkout with the charter-master. As in 2023, we received a windfall of free liquor and groceries from boats returning to the dock at the end of their charters, which delayed our underway time but was well worth it. We had a second delay when minutes after disconnecting our yacht from shore-power, low-voltage alarms sounded on the house battery bank and the port engine battery. The charter-master and base front desk were notified and a technician came over to investigate. His diagnosis was that everything was operating normally, a conclusion that we doubted, and he told us to start an engine or the generator whenever it happened in order to clear the alarm. We were concerned that there was an electrical issue that could deteriorate during our charter and at best would spoil the zen of being on a sailboat, having to run a noisy engine practically 24/7. I was disappointed in the tech’s explanation that low-voltage alarms were perfectly normal (they’re not), especially coming from The Moorings, which markets itself as the “world’s premier yacht charter company.” We had also been warned earlier that our shore-power connection might be lost at any time. The Moorings’ marina infrastructure has not kept pace with the size and electrical complexity of their charter fleet, and tripped breakers are apparently common. It didn’t happen to us, but checking the condition of the dockside power pedestals, I found many of the outlets were blackened and charred, evidence of arcing and overloading and confirming that they’re having problems. 

After concluding that we were on our own to manage our electrical situation, and that we had the skills and experience to handle it, we left Road Town around 11:00 AM. Once outside of the harbor, we turned into the wind to raise the mainsail, and encountered another issue—the main halyard fouled around one of the lazy jack mast fittings. This one we couldn’t blame on The Moorings, and it took a few minutes to figure out and correct. Winds were light at 5-10 knots from the northeast, and we sailed for a bit, then motored to our first stop at Marina Cay. This eight-acre island was uninhabited until 1937, when American writer Robb White and his wife, Rodie, purchased it for $60 and built a home, which still stands today. Robb detailed their tropical life in three memoirs, one of which became the 1958 film “Our Virgin Island,” starring Sidney Poitier.

After attaching to our mooring ball, we went for a swim in the clear and comfortable salt water, nervously marveling at the four-foot barracuda hanging out under our boat. Barracuda have been around for more than 50 million years and are very curious, often approaching close. Though they appear fearsome, with rows of visible sharp teeth, unprovoked attacks on humans are extremely rare. Following our swim, we had happy hour cocktails aboard, then took the dinghy ashore for dinner at Marina Cay Bar & Grill. Map link: Marina Cay, BVI

Captain Mick fixing the main halyard

First swim call

“Sloop John B” parody (lyrics by Grace B)

First dinghy ride and dinner ashore

Tony G, Sue, Mick, Katy, Kathleen, Lisa, Tony B and John

Saturday, Nov 15: We were underway at 8:30 AM, headed across the Sir Francis Drake Channel to The Baths, an iconic BVI tourist attraction consisting of large granite boulders forming tidal pools, arches, tunnels and grottoes. Map link: The Baths, Virgin GordaAs we approached, we saw red flags on shore, meaning that mooring and swimming were prohibited due to rough seas and strong currents. The flags changed to yellow as we got closer, allowing access but advising caution, and we decided not to attempt swimming ashore in challenging conditions. Instead, we sailed up the Drake Channel to Great Dog Island, where we went snorkeling and ate lunch. Map link: Great Dog, BVIThen it was on to North Sound in Virgin Gorda, sailing in 10-15 knot southeast winds, reaching boat speeds of over 7 knots. In North Sound, we picked up a mooring at Leverick Bay Resort and Marina, swam and relaxed, then went ashore for cocktails at the beach bar followed by dinner at the resort’s upstairs fine dining restaurant. Virgin Gorda is the second-most populous island in the BVI after Tortola, and its name is also credited to Christopher Columbus, who thought the island’s profile looked like a large woman lying on her side. North Sound includes about 3,000 acres of protected waters and was a popular anchorage with Elizabethan-era privateers, including Sir Francis Drake. Map link: Leverick Bay, Virgin Gorda, BVI.

Yellow flag warning at The Baths

Great Dog snorkel site



Leverick Bay beach bar


Leverick Bay Resort


Sunday, Nov 16: Winds were light and the seas fairly calm, so we decided to head into open water and motor the 15 miles to Anegada, the northernmost and second-largest island in the BVI. It is the only inhabited island in the archipelago made from coral and limestone, rather than volcanic origin, and its highest point is only 28 feet above sea level. The name Anegada means “flooded” or “drowned” in Spanish and most of its 450 residents live in the only village, called The Settlement. The island is surrounded by the 18-mile Horseshoe Reef, one of the largest in the Caribbean and home to hundreds of shipwrecks, making the entrance to the sole anchorage less straightforward than on other islands. This complication, as well as the long, open-water distance from support services on Tortola, make this unique destination off-limits to many charter boats. 

Chart briefing for Anegada


Anegada is hard to see until you’re close

At 11:30 AM, we tied up to a BoatyBall, a reservable mooring booked online. Soon after, we were boarded by a few small seabirds, presumably looking for a handout. Our next visitor was Sam from Potter’s by the Sea restaurant, who came out to solicit our business that evening. We were sold by his well-rehearsed pitch, and quickly made a dinner reservation, which is mandatory on Anegada, along with ordering ahead when you book. After a quick lunch, some of the crew swam ashore while others followed in the dinghy to do some sightseeing and souvenir shopping. Captain Mick and Sue watched the Vikings-Bears football game on the iPad, while the rest of the crew swam around the mooring, admired the resident sea turtles, rested and goofed off until our 7:00 PM dinner reservation. It was a hot and humid afternoon, with a temperature in the mid-80s, plentiful sunshine and high humidity from the southerly winds bringing in equatorial moisture. Map link: Anegada, BVI


Swimming to shore and back

One of several sea turtles around our mooring 

At dinner, most of us ate Anegada lobster, so fresh that you walk past the live tank on the way to your table. Grilled the Anegada way over an open flame and served with sides, salad and dessert in a casual, beach front setting, it was all delicious. Sam, who is also Potter’s chef, made an appearance from his outdoor kitchen to serenade the five groups of diners with his rich singing voice. The diners next to us were four twenty-somethings sailing aboard a 50+ foot sailing catamaran anchored in front of us. They were friendly and pleasant, but their young age, use of stand-up paddle-boards as dinghies, and frequent absences during dinner provided excellent gossip fodder during and after our meal.


On, Wisconsin!



Monday, Nov 17: By 7:00 AM the wind had backed into the east and grew to 10-15 mph. The skies were partly cloudy, with puffy white cumulus clouds that are typical in the tropics. Sam from Potter’s returned to the boat to deliver ice and haul away trash. We left Anegada at 9:15 AM, with our longest sailing day ahead of us, at 35 miles. We flew on a thrilling beam reach for about two hours and ran our watermaker non-stop, as we had gotten down to about 25% of our total capacity. The wind moderated and we enjoyed another hour of slow sailing, before turning on the engines around Noon as the wind dropped below 5 knots.



At 2:00 PM we moored in White Bay on Jost Van Dyke (population 225), named after a 17th-century Dutch privateer who used the island as a hideout. We went for a quick swim to cool off in the clear turquoise water, then enjoyed Tony B’s homemade chili, which he had prepared while we sailed. After lunch we split up into swim-ashore and dinghy-ashore groups to visit the Soggy Dollar Bar, a world-famous cruiser’s hangout since the 1970s and inventor of the Painkiller tropical rum drink. After returning to Mango Tango as the sun was setting, dinner was a get-your-own meal, followed by beer, wine and cocktails on the “lido deck,” as we’ve come to call the outdoor lounge space over the cockpit. Fun fact I learned today: Lido means “beach” in Italian and is the main upper deck on a cruise ship that is usually the center of social activity.


The Soggy Dollar Bar, Jost Van Dyke



Tuesday, Nov 18: After morning swim call and breakfast, we left White Bay through one of the narrow reef cuts, then practiced motoring and sailing skills for a couple of hours. Winds were brisk at 10-15 knots from the east, with higher gusts during a few rain squalls. Sue set a trip speed record of 8.8 knots under sail before we reefed the main as the apparent wind exceeded 20 knots. After reefing, Mick came close to the full-sail record, logging 8.7 knots. Teachable moment—there is usually only a very small speed penalty, if any, when sails are shortened in higher wind speeds. The reason: As a sailboat gets overpowered, it becomes unbalanced and moves less efficiently, increasing heel, weather helm and rudder angle needed to keep it tracking straight. All of these add drag and slow the boat down, making reefing sails not only safer and less stressful on the vessel and crew, but effectively just as fast. 

We headed north to Diamond Cay, picking up a day mooring and taking the dinghy to lunch at the small but friendly B-Line Beach Bar on Little Jost Van Dyke. The home-cooked food was excellent, the open air dining was relaxing and Katy made a new friend. Map link: Little Jost Van Dyke, BVI

Maneuvering drills

Pointing drills




Planned side trips to the Bubbly Pool on Little Jost and Soper’s Hole on Tortola were canceled due to time constraints, and we sailed around West End and Little Thatch Island back into the Drake Channel. Quickly, the wind and waves were on the nose, so we motored the last two hours with St. John, USVI, close to starboard, arriving aThe Bight on Norman Island at 4:30 PM. The Bight is a large, well-protected, deep-water anchorage, and was another popular stop for pirates and privateers back in the day. Norman Island was named after an 18th-century pirate who once ruled here, and there is credible evidence that he and his clan buried stolen Spanish riches on the island around 1750. Many believe that pirate gold is still there for the taking and that the island was the inspiration for Robert Louis Stevenson’s classic novel, Treasure Island—sentiments that are not discouraged by the BVI tourism industry.


We picked up a mooring, then swam and chilled out, made a quick run to shore for ice, then went to the “Willy T” for drinks and dinner. Officially the William Thornton, named after the British-American physician, inventor, painter and architect who was most famous for designing the United State Capitol building and less famous for being the first Superintendent of the U.S. Patent Office, this floating bar and restaurant is another world-famous cruiser’s hangout, known for its party atmosphere. This is the second iteration of the William Thornton—the original vessel was a 1935 wooden schooner converted into a floating bar in the 1980s. After Hurricane Irma damaged the ship beyond repair in 2017, it was sunk off of Peter Island as a pirate-themed, recreational dive site. The new, 100-foot, steel replacement retains all the amenities and excitement of the original, including excellent fresh seafood, music, dancing, body and water ski shots, and raucous tourists letting it all hang out and jumping into the ocean from the upper deck. The crowd during our visit was small, but most of the other patrons were quite drunk and horny, providing interesting people-watching and other entertainment. Map link: Norman Island, BVI

Ice run to Norman Island

 Being silly on the Willy

Our crew after jumping off the Willy T’s upper deck

Wednesday, Nov 19: We woke up to a reliable east wind of 10-15 knots again, getting underway at 9:30 AM. Our first stop was around the corner at Treasure Point, my favorite snorkeling spot in the BVI. It was a little wavy, which kicked up the bottom sand, but we all had fun and got a great view of reef fish large and small, including a nice school of tarpon. Map link: Treasure Point, Norman Island, BVI

Morning coffee on the Lido Deck

Treasure Point snorkeling

Once back in the Drake Channel, we beat upwind the ten miles to Cooper Island, where we tied off to our reserved BoatyBall, swam, relaxed, and enjoyed a champagne toast to our successful week together. At sunset, we dressed in our finest clothes that were still clean and went ashore to the Cooper Island Beach Club, a small but attractive development of guest cottages, restaurant, gift shop and rum bar, all connected by a lovely boardwalk. Before dinner, we had a semi-important mission to find coffee for the following morning, since we were out. None was for sale ashore, but Captain Mick met a fellow Moorings owner from South Africa who agreed to trade coffee for red wine, something they were low on. A deal was struck, and after an exquisite meal at the restaurant, Mick and I dropped off our crew, then made the exchange on the swim platform of their Moorings 50 catamaran.

Upon returning to Mango Tango, we had a good news, bad news combination of boat issues. On the plus side was that our batteries seemed to have miraculously recovered, and we were no longer receiving low-voltage alarms. The bad news was that the large patio door connecting the main saloon to the aft cockpit malfunctioned, and the door was stuck shut. Fortunately we had another door through the forward cockpit and weren’t locked out, but it was still a nuisance. Troubleshooting revealed a broken latch, which was removed and access was restored. This was our last night aboard, and most folks stayed up as late as they could—I made it until midnight, with three more still awake when I turned in. Map Link: Cooper Island, BVI

Bonus Question: Cooper is an occupational name, derived from a person’s job or trade. Common examples are Carpenter (woodworker), Smith (metalworker) and Taylor (tailor). What work does a Cooper perform? How about Fletcher, Sawyer, Parker, Tyler, Chandler, Wagner, Coleman and Thatcher? (answers at end of post).






Thursday, Nov 20: The anchorage got a little rolly, and I was awakened at 4:00 AM by the malfunctioning sliding door banging open and closed. A nearby ice chest made an adequate door stop and I was able to go back to sleep for a while. We got an early start to maximize sailing time before our yacht was due back and slipped our mooring at 7:30 AM on a partly cloudy day with 80F temperatures and northeast winds at 5-10 knots. It was an easy, six-mile downwind run from Cooper Island to Road Harbour, with some jibing practice thrown in for good measure. Enroute we emptied our holding tanks, ran the watermaker (in that order) and packed our bags, arriving at The Moorings base around 10:30 AM. After tying up and offloading, the base shuttle driver took us to the airport, where we learned that our flight was delayed by 90 minutes. We all used the time to grab lunch, with Kathleen and I enjoying some local chicken and rice at a small kitchen that appeared to be popular with airport employees. We were hungry again after landing in Miami for our connection, and had dinner with John & Katy before boarding our flight home to Minneapolis. We arrived home shortly after midnight and went straight to bed after a wonderful vacation!

Adieu, BVI

Cruise ships in Road Harbour

Back in the barn

The best crew ever!

Bonus Question Answers—Occupational names: Cooper = barrel maker, Fletcher = arrow maker, Sawyer = woodcutter, Parker = park keeper, Tyler = tile maker, Chandler = candle maker, Wagner = wagon maker, Coleman = coal miner, and Thatcher = roofer.

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British Virgin Islands sailing

We took another British Virgin Islands sailing trip with college friends. Returning from 2023 were me, Kathleen, Mick, Sue, John and Katy. N...