Regatta Experiences
Regattas are a very social way to engage in the sport of sailing. It’s a bit different than cruising. Regattas means there are races, winners, trophies, ceremonies and boisterous social events, often with music, drink and sometimes dancing. On the race courses, boats compete against each other. But back at dock, all the sailors come together in celebration. Arabella selects a few cool regattas each year and offers curated “Racing Experiences.” These vary from the super exclusive and luxurious “St Barths Bucket Regatta” to the historic and folksy “Gloucester Schooner Festival.” There is a Regatta Experience for everyone. Read more about our current offerings below and start participating in some of the best regattas in the world.
Newport to Bermuda Race
Biannually, next event is June 2026
The Newport to Bermuda Race is the oldest and most prestigious ocean race in our country. Participating in this event is a multi-month experience which includes team building, training as well as the Safety-at-Sea Seminar. This is the “Mount Everest” of our regatta experiences and designed for serious sailors who love blue water experiences.
St Barths Bucket Regatta
Spring 2026
The Bucket is one of the most exclusive superyacht events in the world. This is also Arabella’s most premium Regatta Experience. This regatta takes place on St Barths which is the most glamorous island in the Caribbean. If you like fashion, drinking champagne and seeing some of the world’s most majestic yachts, this is your once-in-a-lifetime opportunity.
Heineken Regatta
Spring 2026
The Heineken Regatta is often considered to have the best parties of any regatta in the world. Held on the island of St Maarten, you will experience fresh tropical breezes, turquoise waters, warm sunshine and as the name implies, lots and lots of cold beer. This event draws a large fleet of boats and party sailors from many nations. Pack your sunscreen and t-shirts and get ready to have fun!
BVI Spring Regatta
Spring 2026
The BVIs has 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.
Round the Island Race – Martha’s Vineyard
Summer 2025
Martha’s Vineyard is one of the most exclusive 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 in Block Island for some fun and then arrives Martha’s Vineyard for “The Race.” Pack your sun dress and blazer and let’s go yachting!
Gloucester Schooner Festival
Labor Day Weekend 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.
The Great Chesapeake Bay Schooner Race
October 1st-5th, 2024
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.
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