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Classic Sailing Yacht Regattas

Classic Sailing Yacht Regattas

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Regattas are a special part of the yachting lifestyle, steeped in the history of the boating sport and always a sight to behold. Sailing yacht races are among the most spectacular events held each cruising season in the Western Mediterranean, in the Caribbean, and in New England on the East Coast of North America. By chartering a classic sailing yacht you can enjoy the most important classic boat races in style; some clients charter classic boats to participate. Other clients charter classic sailing yachts to enjoy the prime view of spectator on the water as the regatta goes on around them.

Sailing yachts that are ideal for regatta charters are built differently than other styles of chartered yachts. While still comfortable and elegant, these sailing yachts are built for speed and power. Newer racing charter boats might offer sizable guest cabins, but classic racing yachts typically are most spacious on deck, where the crew operate the sails. A classic yacht charter on such a yacht is more about becoming a master of the wind and waves than it is about being surrounded by heavy marble bathtubs in the guest cabins.


In the Western Mediterranean, one of the prime opportunities for regatta charters each year is Les Voiles de St. Tropez, which takes place in late September or early October. New sailing yachts join classic sailing yachts in a field of hundreds of competitors and spectators staffed by thousands of crew. The world-renowned racing is a sight to behold, as is the ambience surrounding the event itself. Often, the world’s most prestigious sailing yachts are on hand for this event, which is considered a finale to the summer yacht charter season in the Mediterranean.


The Caribbean’s most prestigious regattas include the Heineken Regatta on Saint Maarten as well as Antigua Sailing Week, each held during the winter yacht charter season. These regattas, like Les Voiles de St. Tropez, typically draw the finest, most competitive sailing yachts in the region as participants. The Heineken Regatta offers not just a racing division but also a cruising division, in which the races are shorter, more competitive, and often ideal for yacht charter clients. There is an option for racing two or three hours per day, and then relaxing as one would during a “normal” luxury yacht charter.


In New England, the annual New York Yacht Club cruise includes some of the most beautiful racing yachts based on the East Coast of North America. This summertime event is organized around port-to-port races that take place during the course of several days, so participants not only get to compete, but also to visit and explore multiple destinations along a coastline such as the one in the state of Maine. Fans of classic yacht charters may join this regatta as participants or as spectators, perhaps combining the regatta itself with a few days of chartering around Newport, Rhode Island, where the Manhattan-based New York Yacht Club offers a mansion with guest rooms and fine dining for its membership to enjoy after the races.