Chartering a Traditional Sailing Ketch To See the St Barths Bucket Regatta and More
The email from Zeke at the American Sailing Association announced that two cabins had become available for a once-in-a-lifetime voyage to the St. Barths Bucket Regatta. With the cold winter weather still with us in Hampton, VA, Trena and I jumped onboard for what turned out to be an incredible week of charter sailing in the Caribbean and watching super yachts from around the world race around St. Barths.

We arrived in Antigua and quickly made our way from the airport to the Marinaside Restaurant in Falmouth Harbor where we met 19 other sailors that would become good friends by the end of the week. After happy hour to get acquainted and slow down to island time, we were welcomed aboard by the crew of the Rhea, a 177-foot traditionally built, yet modernly equipped, two-masted Bermuda staysail ketch. Later that evening, Captain Richard discussed our sail plan, which included sailing from Antigua to St. Barths, hanging around for a few days to watch the regatta, heading southeast to Barbuda, and returning to Antigua at the end of the eight-day voyage.
Beam reaching to St. Barths
The steady easterly trade winds of the Caribbean never disappoint a sailor. This proved true the next morning as we got underway with full sails on a beam reach, heading direct for St. Barths some 80 miles to our northwest. The deck crew on Rhea welcomed all of us to help set and trim her five sails, including a Yankee sail, a flying staysail flown between the foremast and mainmast on a wishbone boom, sometimes referred to a fisherman’s sail.
While some of us worked the deck, others enjoyed views sitting in the netting on each side of the bowsprit watching the bow slice through the waves. Still others simply enjoyed the motion of Rhea and the wind in their hair. As the sun set, the stars appeared above the sea with spectacular beauty as the lights of St. Barths appeared in the distance. We arrived at the anchorage just off Gustavia in St. Barths among a fleet of super yachts following an exhilarating 12-hour sail. It was the longest open water sail many of us onboard had ever experienced in some of the best sailing conditions anyone could ask for!

A superfleet ready to race
Early the next day after a morning swim and breakfast, we got underway for the highlight of the trip. The St. Barths Bucket Regatta, held this year from March 12 to 15, blended innovation with tradition as magnificent superyachts from around the world gathered to compete in a thrilling mix of fun and fierce rivalry. We looked on with amazement as 34 sailing yachts reaching lengths of up to 256 feet competed in nine classes, including two Corinthian Spirit non-spinnaker classes, a 90-foot class, and a Maxi 100 class.
As we sailed among the fleet, our captain positioned us for front row viewing so that we could watch the action unfold as the yachts proceeded upwind on their pursuit race around the island. Some of the yachts participating in the event included the 219-foot ketch Hetairos, who was the overall winner, the 213-foot, three-masted schooner Atlantic, the 193-foot ketch Maximus, and 256-foot yacht M5, the largest single-masted sailing yacht in the world.
I’ve been racing for many years in quite a few large regattas, but nothing compared to the thrill of watching this fleet of super yachts competing in a unique blend of camaraderie, competition, and sportsmanship shaped by yacht owners over more than three decades. Of course, a trip to St. Barths would not be complete without a trip ashore for some shopping, French cuisine, and walking along the waterfront of Gustavia among the moored super yachts. If you’re on the island, we highly recommend dinner at Eddy’s Ghetto. You won’t be disappointed.

Frigate birds of Barbuda
With the excitement of the Bucket Regatta behind us, we set sail the next morning for a 45-mile upwind beat to Antigua’s tranquil sister island Barbuda, a low-lying sandbar protected by mangroves. The trade winds had increased to 35 knots, making for sporty conditions as we headed southeast under full sail; nothing that Rhea and her crew couldn’t handle. What fun!
We anchored in the protective lee of the island and went ashore on small local skiffs to explore the Frigate Bird Sanctuary, home to one of the world’s largest colonies of these striking seabirds. We also enjoyed a stroll along Palm Beach, famous for its endless stretch of soft, pink-tinged sand. With a population of around 1500, Barbuda offers a quiet, underdeveloped escape from cruise ships and crowded Caribbean towns.

Back home to Antigua
The final leg of our journey included a beam reach back to Falmouth Harbor in Antigua where our fun began the week earlier. Throughout the 150-mile voyage, we met new friends, sailed the open waters of the Caribbean on a spectacular ketch, visited breathtaking destinations, and enjoyed delicious onboard meals and world-class hospitality.
Our final stop before boarding the flight home was lunch at the Garden Grill near the V. C. Bird International Airport where we enjoyed a final taste of the Caribbean before saying goodbye to our new friends.
Learn more about American Sailing Association adventures at americansailingvacations.com.
About the Author: SpinSheet Century Club member Dave Stalfort sails his Catalina 310 Swept Away out of Hampton and is an active participant in Youth Sailing Virginia and Hampton Yacht Club, as well as a maritime photographer.




