● Arrive in style with Tradewind: New scheduled service from Hanscom Field (BED) in the Boston area to Martha’s Vineyard and Nantucket, in addition to service from New York, makes attending summer regatta weekends even easier, with private-terminal departures, no ferry hassles, and a seamless, elevated travel experience.
● Plan your getaway around iconic island regattas: Highlights include Martha’s Vineyard’s Vineyard Cup and ’Round-the-Island Race, plus Nantucket Race Week, the Nantucket Regatta, and the Opera House Cup, all paired with dining, shopping, beaches, and quintessential New England coastal charm.
● Continue to follow the sailing season beyond the islands: Tradewind can also take guests farther afield, from Newport’s classic yachting events to the British Virgin Islands’ laid-back Caribbean regattas, making it easy to turn the sailing calendar into a summer of luxury escapes.
Sail Into Summer: Your Perfect Regatta Guide
Few summer traditions are as exhilarating as a sailing regatta, where beautiful boats fill the harbor, skilled yachtsmen compete on the water, and a glamorous dockside social scene unfolds on shore. Whether you’re a seasoned regatta attendee or discovering your first luxury sailing experience, Tradewind Aviation provides the best way to get you there in style.
This summer, getting away from the Boston area is even easier thanks to new Tradewind scheduled flights from Bedford, Massachusetts, to Nantucket and Martha’s Vineyard, departing from Hanscom Field (BED). Conveniently located in Greater Boston, Bedford offers a seamless airport experience that brings effortless island travel closer to Boston and the surrounding suburbs.
Daily service begins in June, just in time for the peak summer season. Flying Tradewind from Bedford makes the journey remarkably easy: guests arrive just 30 minutes before departure and skip crowded terminals, long security lines, and ferry schedules in favor of a smooth, direct flight aboard Tradewind’s modern Pilatus PC-12 aircraft. Guests in the New York area can also enjoy this effortless travel experience by taking advantage of Tradewind’s scheduled service flights from the private terminal at Westchester County Airport (HPN) to Nantucket and Martha’s Vineyard. Tradewind’s Nantucket service runs year-round, with Martha’s Vineyard flights operating between Memorial Day and Thanksgiving.
Here are a few of the premier summer regattas around which to plan a long-weekend escape to Martha’s Vineyard or Nantucket, where sailing is woven into the fabric of the social season. With Tradewind’s direct flights from Bedford and New York, you can arrive with plenty of time to settle in before the festivities begin.
July on Martha’s Vineyard: the Vineyard Cup and ’Round-the-Island Race
Summer on The Vineyard offers countless ways to turn a race weekend into a full island escape, from beautiful beaches and charming towns to excellent local oysters. For travelers seeking standout events in Martha’s Vineyard, few experiences capture the season quite like a Martha’s Vineyard regatta. Two of the most memorable sailing races happen in July.
The Vineyard Cup marks the unofficial start of big boat racing on the island. Hosted out of Vineyard Haven, this celebrated Martha’s Vineyard regatta brings more than 100 yachts to Vineyard Sound and Nantucket Sound for three days of spirited competition and lively shoreside festivities, making it a highlight for anyone interested in sailing Martha’s Vineyard.
The weekend begins Thursday evening with a waterfront buffet and auction, where sailors, supporters, and island guests gather for fresh seafood, drinks, music, and fundraising in support of Sail Martha’s Vineyard, a nonprofit organization dedicated to protecting and perpetuating the Island’s maritime heritage, culture, skills, and the surrounding environment. Friday brings the first day of racing, with the fleet heading into the sound and an energized atmosphere building along the waterfront. Saturday morning’s Parade of Sails is among the weekend’s most photogenic traditions, as the boats depart in full view of the harbor before another day of racing. That evening, the celebration continues at the Sail MV boathouse beach party, a favorite for its food, drinks, music, and sunset views. Sunday closes the weekend with final races and a distinctly celebratory mood on the waterfront.
The Edgartown Yacht Club ‘Round the Island Race is another one of Martha’s Vineyard summer events. An East Coast tradition since 1938, this is an iconic 55-mile circumnavigation of Martha’s Vineyard. The historic offshore race draws teams from across the country and abroad to compete in one of New England’s most respected distance races. It is also a standout on the summer social calendar, and a natural addition to any Edgartown Race Weekend itinerary.
Festivities begin Friday with the Welcome Party, where crews and guests gather on the Clubhouse and Anchor Deck ahead of race day. On Saturday, the fleet sets out early to circle the island, returning by evening for a lively finish to the day, with restaurants offering special menus and bars staying open late. The weekend concludes Sunday morning with the presentation of the Venona Trophy and other awards. For visitors looking for memorable events in Martha’s Vineyard, this is one of the island’s most storied summer traditions.
August in Nantucket: Race Week, the Nantucket Regatta, and the Opera House Cup
Nantucket is rich in historic charm, from its cobblestone streets lined with shops, galleries, and restaurants to its elegant Greek Revival homes and gray-shingled cottages. Between a visit to the Whaling Museum and a stroll along the scenic Sconset Bluff Walk, the island offers plenty to fill a summer weekend beyond the regattas happening during Nantucket Race Week, one of the most anticipated events of the summer sailing season.
The nine-day celebration in August celebrates competition, tradition, and island festivity, complete with dockside social gatherings and elegant harbor views. Hosted by Nantucket Yacht Club and Great Harbor Yacht Club in support of Nantucket Community Sailing, the racing unfolds across Nantucket Harbor and Nantucket Sound.
The week typically opens in early August with the Youth Opti & 420 Regatta, bringing family-friendly energy to the harbor and yacht clubs. From there, the schedule shifts into one-design racing, including kite and winging events, along with IODs, J/70s, Hobie 16s, Melges 15s, and Lasers while the Harbor Race, Women’s Regatta, and Celebrity Invitational build momentum toward the Nantucket Regatta, one of the week’s premier big-boat events.
The grand finale comes in mid-August with the Opera House Cup, a prestigious regatta often described as the crown jewel of wooden boat racing. The first all-wooden, single-hulled classic boat regatta on the East Coast, it attracts some of the finest classic wooden sailboats in the country, including vintage designs from before 1940 and notable yachts that once competed for the America’s Cup. They create a spectacular display on the water, and an elegant conclusion to one of summer’s most celebrated sailing weeks.
Continue the Season in Newport and Beyond:
If regatta season leaves you wanting more, Tradewind can take you to even more sailing events this year. Private charter flights make it easy to extend the summer sailing circuit to Newport, which served as home to the America’s Cup for 50 years. There, marquee events like Safe Harbor Race Weekend in August and the Newport Classic Yacht Regatta in September offer the chance to see beautifully maintained vintage yachts and world-class racing in one of New England’s most famous sailing destinations.
Tradewind also offers seasonal scheduled service to the British Virgin Islands via its hub in San Juan, Puerto Rico, with direct flights to Tortola and Virgin Gorda that eliminate the extra ferry logistics often associated with reaching the islands. The result is a smoother path to a luxurious Caribbean escape, where regatta weekends can be paired with villa stays, beach lunches, snorkeling excursions, and sunset dinners. Private charters are offered year-round from throughout the Eastern Caribbean.
Highlights of the BVI summer sailing calendar include Foxy’s Wooden Boat Regatta in Jost Van Dyke in May, beloved for its island character and heritage atmosphere; the Lowell Wheatley Anegada Pursuit Race & Rally in June, a classic laid-back event hosted by the Royal BVI Yacht Club; and the Firecracker 500 in July, a spirited day of racing hosted by the West End Yacht Club.
From New England’s classic yacht harbors to the turquoise waters of the Caribbean, Tradewind makes it easy to follow the regatta calendar in style.
To learn more about Tradewind’s private charter and scheduled flights and booking your vacation, please visit our website. To receive a private charter quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-800-376-7922 option 3. For questions regarding scheduled flights, contact our scheduled service team at scheduledservice@flytradewind.com or 1-800-376-7922 option 1.