Regatta Experiences
“Regatta Experiences” are specially curated trips for “social” sailors who like the thrill of competition plus hanging out with racers. Regattas are very social gatherings. They include races, winners, trophies and parties, often with music, drinks and dancing. If you like hanging out with fun and high energy people, you should try one of our great Regatta Experiences. Let’s have some sailing fun.
The idea for a “Regatta Experience” goes back in history to a time when owners and their guests would come aboard large yachts for a race. These owners were often successful business people with lots of enthusiasm but not much time for training. They relied on professional crew to sail their boats and they rode aboard with friends who had enjoyed the fun and thrill. Names like Cornelius Vanderbilt, JP Morgan, Vincent Astor and Sir Thomas Lipton come to mind.
Commodore Michael Fortenbaugh of the Manhattan Yacht Club grew up racing and attending regattas. They made a big impact on him. Now he wants to share this experience with more people. He has directed Arabella and her professional crew to select a few regattas so that people can sign up and experience regatta culture without having to spend years training. Our lives are just too busy!
Arabella’s Regatta Experiences range from our most exclusive, the “St Barths Bucket,” to the friendly and historic “Gloucester Schooner Festival.” There is a Regatta Experience for everyone. Read more about the experiences below. There are 3 regattas in the Caribbean starting in March 2026 and also 3 regattas on the East Coast starting in summer 2025. Regatta Experiences are open to everyone, from the novice sailor to a retired expert.
St Barths Bucket Regatta
March 10-16, 2026
The Bucket is one of 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 $4,800 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 $2,800 per person.
Gloucester Schooner Festival
August 28 – September 2, 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 118 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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