It’s not unprecedented, but rather unusual that I ever sail on the same boat twice when chartering. Now, it is expected in the British Virgin Islands, with my standing invitation as First Mate aboard AIRSHOW, John McSherry’s (Mick) Leopard 4200 three-cabin sailing catamaran in The Moorings’ fleet. Here’s my trip report from our latest voyage:
Tuesday, May 5: Mick and I were up at 3:00 AM to catch a 5:30 AM flight out of Cincinnati, OH. The main airport serving Cincinnati is actually in Northern Kentucky, about 13 miles from downtown, and the airport code, CVG, comes from Covington, KY, the nearest town when the airport first opened. We planned to fly to the islands a day early, as the availability of standby seats was better and it would give us time to check on the maintenance punch-list for AIRSHOW. We connected through Atlanta to St. Thomas, USVI, without any issues, and were feeling pretty smug and satisfied by flying standby for free, one of the perks of Mick’s employment with Delta Airlines. In St. Thomas, we had to wait more than hour for the ferry to Tortola, BVI, then cleared customs and arrived at The Moorings base in the early evening. Mick and I stowed our seabags, then explored Road Town on foot, looked for a restaurant, but didn’t find anything to our liking and went back to The Moorings casual dining restaurant for dinner.
![]() |
| Towel art on our bunks |
Wednesday, May 6: We slept until after the 5:45 AM sunrise, then Mick did charter/owner business and checked up on the yacht’s maintenance and repair items. The main issues were a leaking barbecue grill and an inoperative wind instrument, which the base maintenance folks got to work on. It was later in the spring than we’d ever visited here before and while the air temperature was in the mid-80s, about the same as on previous trips, the dew point was an oppressive 74F, far more humid.
![]() |
| Starlink antenna above the helm spoiled us with satellite internet on the whole trip. |
We shopped for provisions at several grocery and liquor stores to get most everything on our list, then awaited John Prosen and Tim Chisser, our last two shipmates and Mick’s neighbors in Hayward, WI. When they were settled aboard, we went to the base’s pool bar for a complimentary rum punch, then ate a spectacular dinner at Charlie’s, The Moorings’ fine-dining restaurant. Map link: The Moorings, Road Town, Tortola, BVI
![]() |
| Tropical humidity, as seen in the grocery store coolers |
Thursday, May 7: I awoke at 6:00 AM; it had rained overnight but I slept through it. I was the last one out of the bunk, and Mick, John and Tim were already at the helm training. We had coffee and tea aboard, went to the Island Roots Cafe on the base for breakfast burritos, then met Chartermaster Brad for our pre-underway checkout aboard Airshow. There were two more maintenance items that kept us at the dock: the cabin’s forward door latch fell off last night, and the starboard jib car broke during our morning orientation. Both were fixed within an hour or so, then we cast off the lines at 10:30 AM in 83F temperatures and a 15 mph east wind. We beat upwind into a light chop on the Sir Francis Drake Channel, known as Freebooters’ Gangway during the Golden Age of Piracy in the late 17th and early 18th centuries. The waterway was later named in honor of Drake, the most renowned privateer of the Elizabethan era. Bonus Question: What are the differences, if any, between pirates, privateers and buccaneers? (answer at end of post)
Mick set our initial daily speed record of 6.4 knots, we ate sandwiches for lunch underway, then motor-sailed past The Dogs until we arrived at the entrance to North Sound, Virgin Gorda. Around 3:30 PM, we picked up a mooring ball between Saba Rock and Bitter End Yacht Club at the far east end of the harbor, then called Rum Runner, a floating drink delivery service based in the Bitter End mooring field. Mick discovered them on his last trip in March, and had the silicone souvenir cups to prove it. Orders are taken over the phone, radio or by flagging down the delivery dinghy (which we did), then the frozen drinks are made to order in a solar-powered, soft-serve ice cream machine aboard the mother ship and brought to your boat, typically accompanied by rescue dog Drake or Sandy. After our ice-cold Rum Runners and Bushwackers, we swam and relaxed before taking our dinghy ashore to Saba Rock Resort, where we had a dinner reservation. Set on a one-acre island, the resort has been around since the 1960s, and includes a marina, waterfront restaurant, bar and sunset deck, spa, guest rooms, old phone booth, aquarium, and nautical museum, complete with a 16th-century boat anchor. Map link: Saba Rock, North Sound, Virgin Gorda
![]() |
| Rum Runner delivery w/ Sandy |
![]() |
| Saba Rock Resort |
![]() |
| The view from our dinner table |
Friday, May 8: The trade winds blew steadily all night and the boat’s motion was familiar and made for easy sleeping. Our tank water tasted off before we left port and we were trying to use it up quickly, contrary to the cruising norm of always conserving water in the tropics. Another tenet that we willfully violated was running our watermaker in the mooring field. Many ports have dirty water that will clog the system’s membranes, but we were in 30+ feet of clear-looking water near a channel open to the Atlantic with few other boats around, so we went for it. John made eggs and sausage for breakfast, and we were entertained by watching the local diver conduct mooring ball maintenance.
We got underway at 9:15 AM and motored a couple of miles to Prickly Pear Island for anchoring practice. The anchor didn’t grab on our first attempt and Mick heard a metallic noise coming from the port side when the engines were reversed. Concerned that there was a problem with the port engine, transmission, or sail drive, we called The Moorings base, and got their on-call North Sound mechanic to come check it out. Like our trip in January, the response time was impressive (less than 30 minutes) and we were relieved, and more than a little embarrassed, to get the diagnosis—the noise was coming from our barbecue grill. Before we left Road Town, the leaking grease tray had been replaced and the grill remounted to better clear the dinghy davits, but now something was rattling inside while the boat backed up. We probably could have figured this out for ourselves, but the mechanic was good-natured and also relieved that he didn’t have to do anything further. We resumed our anchoring drills, then went sailing, broad and beam reaching, with Tim tying Mick’s 6.4-knot speed record.
Our intended anchorage for the night, Lee Bay on Great Camanoe Island, was attractive and deserted, but a foul odor coming off of an upwind pond quickly drove us away—John unofficially renamed this location “Loo Bay.” Our next choice was White Bay on Guana Island, but it was crowded and the mooring balls were too close together, with a significant risk of hitting another boat. Plan C was to anchor at Monkey Point, but we had to avoid coral heads close to shore and stay out of the way of the national park day moorings. We were careful and patient, finding a nice sandy spot in 12 feet of water, and when we snorkeled over the anchor, it was dug in textbook-style and guarded by a small yellow ray. Teachable moments: Always have a Plan C when cruising, and include it in your morning crew briefing. And inspect your anchor, if possible, to ensure that it’s set properly. Some late-afternoon rain squalls rolled through, a few boats came and went from the park moorings, and one tied up for the night (illegally)—I was somewhat irked by this but minded my own business. I’m pretty sure that we had a great evening, played Farkle (a dice game), Mick mixed drinks and made something delicious for dinner, but I really can’t remember. Teachable moment: Take better notes for the blog. Map link: Monkey Point, Guana Island
![]() |
| Ready to drop anchor |
![]() |
| Rain squall, and the scofflaw that parked overnight on a day mooring. Yes, it’s a Moorings’ vessel. |
Saturday, May 9: It was a lazy morning, with carbon-copy weather from the day before—temperatures in the low 80s, east winds at 10-15 knots and blue skies dotted with puffy cumulus clouds. We ate yogurt, granola and berries for breakfast, then Tim and John swam in to shore near a small landing with a beach on the other side of the point. The anchor was hauled up at 10:15 AM, then we practiced some motoring drills under the protection of Monkey Point. We set sail, cleared Guana Island, and got into the open Atlantic Ocean and its two-foot seas. Mick hit a new speed record of 7.5 knots during a mostly-downwind leg, with plenty of jibing practice (“gybing” if you’re British). We stopped for lunch at Diamond Cay, enjoyed a nap, then Tim, John and I took the dinghy ashore to hike to the Bubbly Pool, a natural tidal pool with waves coming through an opening in the rocks. Map link: Bubbly Pool, Jost van Dyke, BVI. It was busy, with a large group of Americans present, but not at all bubbly, with very little surf coming in, presumably due to calm conditions and low tide. We hiked back to the dinghy, grabbed a drink at Foxy’s Taboo before returning to AIRSHOW. We motored over to Little Harbour on Jost van Dyke, picked up a mooring deep in the bay and sheltered from the waves. Mick made gin and tonics for happy hour, John cooked an amazing dinner of red snapper, pesto pasta and salad, followed by more Farkle until bedtime. Map link: Little Harbour, Jost van Dyke (Garner Bay on some charts and maps)
Sunday, May 10: I don’t remember exactly why we decided to sleep without air conditioning, but we left it off, which meant no generator running all night long. I enjoyed a peaceful night’s sleep, until the boat drifted and began banging against the mooring ball, and a passing rain shower woke me up again, but only long enough to close the overhead deck hatch. The overnight low was 77F and it stayed humid, but the steady breeze kept me comfortable and it was delightful to sleep aboard without the noise and vibration of the generator and air conditioners.
As soon as the sun came up, the wind began building to 15-20 knots. We got underway at 8:30 AM, sailing under jib only for the five-mile hop to Soper’s Hole on the western end of Tortola. We grabbed a reservable mooring, but did not reserve it, and took the dinghy in for provisions two at a time, in case we had to vacate the mooring quickly. Map link: Soper’s Hole, West End, Tortola
We left Soper’s Hole (West End to locals) and got back into the Drake Channel between Tortola and St. John, USVI. Sailing under reefed main and full jib, Mick set a new speed record of 7.6 knots in 1-2 foot seas and 20-25 knots of wind. In the lee of Norman Island, we practiced heaving to, one of my favorite sailing maneuvers, then moored at Privateer Bay, trying out a new mooring ball pickup method—we grabbed the mooring pennant from the starboard hull rather than the main crossbeam at the centerline, which gave the skipper better visibility of the buoy on the final approach. There was excellent snorkeling at the southern end of the bay and we had plenty of free time to enjoy the water and scenery. Mick made old-fashioneds for happy hour, then jambalaya for dinner. We all played Farkle, then Mick and I stayed up late playing cribbage. Map link: Privateer Bay, Norman Island, BVI
Monday, May 11: Mick and I both logged online for the 7:00 AM BoatyBall scramble to nab a mooring at Cooper Island, probably the most popular anchorage in the islands. The excellent restaurant, cozy resort and proximity to Road Harbour make it a popular first or last night stop for a charter and the mooring reservations are typically gone within a minute. We both missed our first attempt at 7:00, but I got one on the second click and sure enough, everything was booked by 7:01. There are first-come, first-served moorings available, and they’re cheaper, but knowing you have a spot is comforting, and you aren’t watching the clock all day to get in early enough and not know for sure. It’s also safer, having witnessed (and participated in) boat drag races through the mooring field to get the last vacant buoy.
At underway time, Mick practiced picking up a mooring ball by himself, which he made look easy, then we raised the sails. We turned northeast and beat upwind into a stiff 15-25 knot breeze in the Drake Channel, getting plenty of tacking practice and AIRSHOW pointing closer to the wind than I expected. Speed records were repeatedly smashed, topping out at 9.4 knots with yours truly at the helm.
At my request, we did a close approach of uninhabited Dead Chest Island, a legendary location in BVI pirate lore. The story goes that the pirate captain Blackbeard (Edward Teach) marooned a group of his men on the island as punishment, with nothing but a cutlass and a bottle of rum each. Thirst and hunger eventually drove those that hadn’t killed each other to escape by swimming to nearby Peter Island, but all drowned and washed up on the beach, known as Deadman’s Bay. The tale allegedly inspired Robert Louis Stevenson’s famous pirate shanty from his 1883 novel, Treasure Island:
Fifteen men on the dead man's chest—
...Yo-ho-ho, and a bottle of rum!
Drink and the devil had done for the rest—
...Yo-ho-ho, and a bottle of rum!
...Yo-ho-ho, and a bottle of rum!
Drink and the devil had done for the rest—
...Yo-ho-ho, and a bottle of rum!
In fact-checking this story, I found no evidence that any of it was true, and couldn’t even verify that Blackbeard ever sailed in the Virgin Islands. Furthermore, charts existed with the name Dead Chest Island long before Blackbeard’s time—the name coming from the island’s profile, which somewhat resembles a coffin, called a “dead man’s chest” by seafarers. As for Stevenson, I found it far more probable that his novel—and the fictional peg-legged, parrot-toting antagonist Long John Silver—inspired the Blackbeard tale, rather than the other way around. It is also widely believed in the BVI (and promoted by the Board of Tourism) that nearby Norman Island was the inspiration for Treasure Island, which is possible, although Stevenson never visited any part of the Caribbean. Map link: Dead Chest Island, BVI
![]() |
| Dead Chest Island (center) and Deadman’s Bay (right) |
We tied up to our BoatyBall, ate a late lunch, napped, swam and showered. Later we dinghied ashore for drinks at the Cooper Island Beach Club Rum Bar, followed by an amazing dinner with outstanding service at the club’s restaurant, probably our favorite place in the islands. Back on AIRSHOW, we played more Farkle and enjoyed gin and vodka tonics before turning in early. Map link: Cooper Island Beach Club, BVI
Tuesday, May 12: Our alarms went off at 5:45 AM, and we cast off of our BoatyBall before 7:00 AM, arriving back at The Moorings base when they opened at 8:00 AM. We quickly offloaded, debriefed and caught a taxi to the ferry terminal for the one-hour ride back to St. Thomas, passing Little St. James Island, now infamous as a major location in Jeffrey Epstein‘s underage sex trafficking network. Map link: Little St. James Island, USVI
At the St. Thomas airport, we encountered the slowest and most frustrating security experience that I’ve ever had. The line wasn’t that long, but it took almost three hours to get through the USDA agricultural and TSA screenings, even with Pre-check. The area was hot, humid and overcrowded, the line moved slowly and people were on edge, worried about missing their flights. Airport officials here advise passengers to arrive three hours before their flights, which seemed ridiculous for such a small airport, but we saw that it was sound advice. Because of the ferry schedule, three hours wasn’t possible for us; 2.5 hours was, but Mick and I missed our intended flight to Atlanta by only 10-15 minutes. We arrived at the gate, watched the plane roll away and checked in with the gate agents about getting on the next flight. Things looked good, until they didn’t—the plane wasn’t full, but it was overweight, and couldn’t take any extra passengers, Our only chance was if ticketed passengers were delayed in the security line and missed the flight, and I felt awful hopng for that outcome. It happened, and as we investigated other options to get off the island, our names were called. All four of us agreed that this was a terrible experience and that we would never fly out of STT airport again. We had a tight connection in Atlanta, and after saying goodbye to Tim and John, Mick and I made a mad dash through ATL’s huge facility, making it to our Cincinnati flight with about ten minutes to spare. We returned to Mick’s place in Kentucky around 10:30 PM, microwaved some White Castle sliders for dinner and went straight to bed.
Bonus Quiz: Test your knowledge of the seas (answers at end of post)
1. What sea does not touch any coastlines?
2. Which sea is really a lake? Hint: It’s extremely salty.
3. What modern sea is now nearly dry?
4. Where is the Sea of Serenity?
5. What do you call a lover of the seas and oceans?
6. What were the original “Seven Seas”?
More sunset pics:
Bonus Question Answer: A pirate is anyone who robs or attacks ships at sea. A privateer was a state-sponsored, quasi-military marauder licensed by a government to attack and plunder their enemies. Privateers occasionally violated their orders and seized vessels of nations not designated in their commissions, blurring the lines between privateering and piracy. Buccaneers were a type of pirate specific to the Caribbean. The name was derived from the French word “boucan,” an indigenous meat smoker. The original buccaneers were nomadic hunters on the island of Hispaniola who sold preserved meat to ship’s crews. When the Spanish tried to drive them out in the 17th century, the “boucaniers” turned to piracy and preyed on Spanish ships. The term was eventually Anglicized to its current spelling.
Bonus Quiz Answers:
1. The Sargasso Sea in the North Atlantic is bordered entirely by oceanic currents rather than land masses. It contains the islands of Bermuda and is recognizable by its bright blue water and yellow-brown floating Sargassum seaweed.
![]() |
| Source: Wikipedia |
2. The Dead Sea is a landlocked, hypersaline lake bordered by Jordan, Israel and the West Bank. It contains 34% salt, 10x more than the ocean, and lies 1,443 feet below sea level, making its shores the lowest land on earth. Map link: The Dead Sea
3. The Aral Sea on the Kazakhstan-Uzbekistan border, began shrinking in the 1960s, when water from feeder rivers was diverted for Soviet-era irrigation projects. By the 2000s, it was 90% dry and its 1,100 islands gone. Map link: Aral Sea
![]() |
| Aral Sea before and after. Source: Wikipedia |
4. The Sea of Serenity is located on the visible face of the Moon. It is a smooth plain, about 420 miles wide and was the site of the Apollo 17 landing in 1972.
![]() |
| Sea of Serenity (circled). Source: Wikimedia Commons |
5. A thalassophile is a person with a deep love and emotional connection to the water. The word comes from the Greek thalassa (sea) and phile (love).
6. The phrase “Seven Seas” dates back to as early as 2,300 BC and was popularized by the ancient Greeks, who mainly sailed the Adriatic, Aegean, Black, Caspian, Mediterranean, Red Sea and Persian Gulf.

































No comments:
Post a Comment