Regatta Experiences
Thrilling Competition and Fun Social Events
Step into the timeless glamour of yachting and experience the thrill of competition and the exuberance of regatta social events with Arabella’s new “Regatta Experiences.” Inspired by the golden age of sailing, when legendary names like Vanderbilt, Morgan, and Astor gathered their friends for spirited regattas, these modern adventures let you savor the same excitement and camaraderie. Commodore Michael Fortenbaugh grew up racing regattas which inspired him to create this program to share the racing lifestyle with more people. Our specially curated Regatta Experiences are designed to bring you the excitement, camaraderie, and celebration of iconic events. Arabella’s crew will expertly handle the boat, leaving you free to enjoy the excitement on the water and the community of social events ashore.
Arabella’s Regatta Experiences range from the world’s most exclusive “St Barths Bucket,” to the friendly and historic “Gloucester Schooner Festival.” There is a Regatta Experience for everyone —whether you’re a novice sailor or a seasoned expert. Read more about the experiences below. Each year there are three regattas on the East Coast in summer and three more regattas in the Caribbean in winter.
St Barths Bucket Regatta
March 10-16, 2026
The Bucket is the most exclusive superyacht regattas in the world. This is also Arabella’s most premium Regatta Experience. The Bucket takes place on glamorous Caribbean island of St Barths. If you like fashion, glamour and seeing some of the most majestic superyachts in the world, this is your once-in-a-lifetime opportunity. Starting at $4,590 per person.
Heineken Regatta
March 3-9, 2026
The Heineken Regatta is often considered to have the best regatta parties in the world. Held on the island of St Maarten, this regatta features fresh tropical breezes, turquoise waters, warm sunshine and as the name implies, lots and lots of cold beer. The Heineken Regatta draws a large fleet of boats and sailors from around the world. Pack your sunscreen and t-shirts and get ready to sail all day and party all night! Starting at $3,800 per person.
BVI Spring Regatta
March 31- April 6, 2026
The British Virgin Islands are considered the best cruising grounds in the world. This is a small group of islands filled with friendly people and a low-key lifestyle. The sailing is excellent and the nightlife is enjoyable, but not over the top. If you are looking for your first Caribbean regatta to try, this is the place to begin. Starting at $2,800 per person.
Round the Island Race – Martha’s Vineyard
June 15-22, 2025
Martha’s Vineyard is one of the most exclusive summer communities in our country. Their big event is the “Round the Island Race” organized by our friends at the Edgartown Yacht Club. Arabella offers a week long experience which starts in New York Harbor, stops by Block Island, and then arrives at Martha’s Vineyard for “The Race.” Pack your blazer and sun dress and let’s go yachting! Starting at $2,200 per person.
Gloucester Schooner Festival
August 28-September 3, 2025
The Gloucester Schooner Festival, organized by Maritime Gloucester, features schooners gathering in Gloucester Harbor annually. The event includes sailing, racing, and dockside exhibits, attracting traditional sailing and wooden boat enthusiasts. Starting at $1,800 per person.
The Great Chesapeake Bay Schooner Race
September 30 – October 6, 2025
The race kicks off in Baltimore, Maryland, and concludes 127 nautical miles away in Norfolk, Virginia. Participation is welcome for all schooner-rigged vessels, appealing to traditional sailing and wooden boat enthusiasts. Starting at $2,200 per person.
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