2026 BVI BoatU.S. Member Flotilla Recap: Island Highlights & Photos
The Moorings has a long-standing relationship with Boat Owners Association of The United States (BoatU.S.), an organization that supports recreational boaters across the country. In 2014, we partnered to create the annual BoatU.S. Flotilla, bringing members together for a guided yacht charter vacation in one of the world’s most memorable cruising destinations. This year, we returned to the British Virgin Islands for a week of boating, island-hopping, snorkeling, shared stories, and plenty of laughs along the way.
Here’s my firsthand look back at the 2026 BoatU.S. Member Flotilla in the BVI:
Day 1
To celebrate the 60th anniversary of BoatU.S., our 2026 Member Flotilla featured a special guest: Captain Glenn Shephard, star of Bravo’s Below Deck Sailing Yacht and Brand Ambassador for The Moorings. This year’s lead boat in the beautiful British Virgin Islands was crewed by local Captain Marlon Williams, Tina Huewe (Marketing Manager for The Moorings US), and Stacey Wigmore (Managing Editor of BoatU.S. Magazine), along with her partner, Griff Drew Jr.
Participants used their first afternoon at The Moorings Tortola base to attend the mandatory boat and chart briefings and to take care of any provisioning needs before settling in to enjoy the base amenities.
Our fun-filled welcome cocktail gathering that night at the pool bar made one thing clear right away: we had an excellent group of people to discover “The Sailing Capital of the World” with in the week ahead.
One of the things we love most about our flotillas is that they bring people from all walks of life together around at least one shared interest: boating. Over the week, we discovered we had much more in common and shared plenty of stories about work, travel, family, parties, and life on the water. While the BoatU.S. Member Flotilla includes just one organized group dinner, we usually ran into each other at the most popular restaurant ashore each night. Later in the week, we also made friendly visits to other flotilla participants’ boats to share a few drinks and exchange boat ownership stories and cruising experiences.
Many participants did not own boats as large as their charter vessels back home, but everyone adjusted quickly to their new vacation platforms. Having our experienced lead flotilla skipper, Captain Marlon, along with Captain Glenn, gave everyone the confidence to jump into the adventure. Cruising in the Caribbean is different from boating on the lakes, inlets, and rivers many BoatU.S. members know best, but the BVI is an excellent cruising ground for first-timers, thanks to its short cruising distances and line-of-sight navigation.
Day 2
After a few final preparations and the first of our daily flotilla captains’ briefings with Captain Marlon, we headed out to our first stop: Norman Island. Because the seas were choppy that day, we couldn’t snorkel at The Indians, so we continued on to the mooring field, where many participants had the chance to pick up a mooring ball for the very first time. Most succeeded on their first try. Well done!
Once safely secured to their mooring balls, the group split up. Some headed out by dinghy to snorkel at The Caves, while others went straight to the world-famous floating bar, the Willy T. Good drinks, casual bar food, and a few jumps from the second deck made for a memorable first introduction to the BVI.
After getting our fill of this iconic stop, we later headed over to Pirate’s Bight restaurant, which delivered exactly the upscale yet relaxed island atmosphere we were hoping for. An unexpected power outage at the restaurant extended our visit a little longer than planned, but that is all part of the experience when traveling through the islands.
Useful advice: When going out for dinner in the evening, don’t forget to bring a flashlight — and remember your dinghy number!
Day 3
The next morning started early as we made our way to the next stop: The Baths on Virgin Gorda. In fact, many days began at little before 7 a.m. for at least one person on each flotilla boat as we tried to reserve a Boaty Ball in the locations where the advanced mooring ball reservation service is available.
It’s always smart to get to The Baths early, and that day the dinghy line separating the cruising area from the swimming and snorkeling area was definitely put to good use.
Because The Baths draws so many visitors, the route is now one-way. After swimming in, we made our way up the hill to pay the $3-per-person National Park fee, which is separate from the general BVI National Park Permit paid as part of the charter. From there, we enjoyed the incredible views before starting our descent to Devil’s Bay, where the world-famous maze of massive granite boulders begins. Walking through small sea pools, following the marked path up and down wooden ladders, and passing through dim grottoes and sunlit canyons never gets old. At the exit, Poor Man’s Bar waits for the explorers — and after all, it’s 5 o’clock somewhere.
As I swam back to our dinghy, I was grateful that, for the first time after many charter vacations, I had decided to rent a dinghy ladder for this trip. Trust me, it’s a game changer. I highly recommend it!
Once everyone was back aboard our power catamarans, we continued on to Leverick Bay in the North Sound. At the full-service marina, guests could stock up on ice and water. Depending on their interests, participants spent the afternoon exploring the North Sound, with Saba Rock and Bitter End Yacht Club within easy reach, or taking a taxi up the mountain to Hog Heaven for unforgettable views over the islands.
We ended the day with a group dinner at the upstairs restaurant at Leverick Bay, followed by some downstairs dancing as the DJ kicked off the night with crowd-pleasers from the ’70s, ’80s, and ’90s.
Day 4
Anegada, the BVI’s northernmost and flattest island, was the next stop on our itinerary. Our flotilla members had the full day to explore the island on their own, with taxis, scooters, bikes, and Jeeps readily available. The long, quiet beaches at Cow Wreck Beach and Loblolly Beach offered first-class photo opportunities and beautiful beach walks, along with their popular bars and restaurants. That evening, freshly caught Anegada lobster made for an unforgettable dinner at Potters By The Sea.
Day 5
After a quick ride west the next day, we arrived at the iconic Great Harbour on Jost Van Dyke, home of Foxy’s Tamarind Bar. We made sure to get there early and secure mooring balls, then took our dinghies around the bend to neighboring White Bay for visits to Soggy Dollar Bar, Hendo’s Hideout, Gertrude’s, and the many other beach bars lining this beautiful stretch of sand. One member even visited White Bay’s swimming spa and said it was the best massage he had ever had, which sounds like something I should add to my own bucket list.
Foxy’s was busy that evening, and during the after-dinner activities and dancing, the whole group cheered on the two members representing our BoatU.S. Member Flotilla in the “Best Stroker” competition hosted by the local DJ. Captain Noel, congratulations — you made us proud!
Day 6
We couldn’t leave without putting on a little competition of our own, so the next morning we met back at the bar for our first annual flotilla Jenga tournament. We even got to meet the Foxy himself that day!
Things got tense as two representatives from each boat faced off in a suspenseful battle of strategic stacking and steady hands under pressure. I have never been so invested in a game of Jenga in my life. In the end, two boats came out victorious and took home the title of “Flotilla Jenga Kings & Queens” — along with some nice Yeti cups.
On the way from Jost Van Dyke to Cane Garden Bay, some participants made a quick stop at Sandy Cay, one of the BVI’s many pristine, uninhabited islands with a postcard-perfect sandy beach and turquoise water. Others went snorkeling at Sandy Spit or headed straight to our overnight destination to relax and visit Callwood Distillery. Dating back to the 1600s, Callwood is the oldest continuously operating distillery in the Caribbean and produces a variety of rums from locally grown sugar cane.
While plenty of bars and restaurants lined the beach, most of our flotilla participants were happy to relax on their boats that evening, enjoy their provisions, and mentally prepare for yet another BVI highlight ahead.
Day 7
The final stop this year was Cooper Island. The Cooper Island Beach Club offers plenty of ways to refresh and unwind, with its on-site brewery, rum bar, restaurant, boutique, and coffee shop. The large rock formation on the western end of the beach has a dinghy line and offers an easy snorkeling opportunity. The bay at Cooper Island is also well known for turtle and barracuda sightings.
Some guests had to return to base that afternoon because of early flight or ferry connections, but those who stayed all agreed that one last day of snorkeling, relaxing, and enjoying drinks and dinner at the Cooper Island Beach Club was a fantastic end to an amazing week with the BoatU.S. Member Flotilla in the BVI.
We hope to see YOU soon.
Here’s what some past BoatU.S. Flotilla guests had to say about their experience:
“We really had a lot of fun and some great learning experiences! We will definitely be back to The Moorings again.”
– Patrick T., BoatU.S. Flotilla 2026
“Beautiful weather, beautiful beaches, beautiful sunrises, and sunsets! A wonderful time with great friends and the peace of mind of having a lead boat to lend a hand and show the way. Such a wonderful vacation!”
– Sue M., BoatU.S. Flotilla 2019
“We enjoyed meeting everyone, and appreciate your excellent service and attention. We will be back!”
– Mike V., BoatU.S. Flotilla 2018
“Our flotilla leader Dunbar was a long time Moorings captain (21 years) and was terrific. …You couldn’t ask for a nicer or more capable leader. And at the beginning, I had many things to ask, and was not too adept at the helm. The itinerary included 6 separate overnight mooring locations at different islands and although there were only 5 boats in the flotilla, we all had a terrific time.”
– Edward M., BoatU.S. Flotilla 2017
“This trip was the trip of a lifetime that we were fortunate enough to share with 6 very special friends of ours. The beauty of the islands and water, the people we met along the way, the food and drinks, as well as all the laughter shared and time spent together on our beautiful boat, No Worries cannot be expressed enough in this note. The boat accommodations and the itinerary that you put together was top notch; everything certainly surpassed all our expectations!”
– Don C., BoatU.S. Flotilla 2015
“This flotilla has been such a fantastic adventure! Better than we ever hoped for. Hate that it’s winding down, knowing the reality check is coming soon; but all good things must end. You did a wonderful job putting this flotilla together! It was such a great idea, as we never would have attempted this trip on our own. You took good care of us! Thank you for patience — and for making it all possible!”
– Rick and Suzi D., BoatU.S. Flotilla 2014
Captain Glenn’s BoatU.S. Member Flotilla IG Posts
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