Sailing is an ’other-worldly’ experience, much like dancing, hang gliding, and skiing. The thrill and adrenaline rush are intoxicating. It challenges and heightens the mind and body, and inspires the spirit.
Sailing races, called regattas, have been around since ancient Greek and Roman times, and likely older in the Middle East, China, and India. In 1661, King Charles II raced his own yacht in a sail race. Sail racing was very popular in the maritime countries of England and the Netherlands. The oldest yacht clubs were formed in England in 1775, Ireland 1777, Australia 1837, New Zealand 1840, U.S. in 1845, and Canada 1856.
A race sails on a determined course or for long distance on open waters. Sailing regattas are sponsored by yacht clubs and corporations. It is an expensive sport due to the cost of a boat or yacht, crews, travel, events, promotion, and prize money.
America’s Cup and Louis Vuitton Cup
The world’s oldest international competition, the America’s Cup yacht race was formed in 1851. The race is held every 3 to 4 years, the last one in 2024. Several challenger races are held to determine who will be the single challenger against the defending title holder. For 132 years it was a British vs. American race, the title was held by the New York Yacht Club from 1857 to 1983.
The Royal New Zealand Yacht Squadron won the race in 2017 beating the Oracle Team USA. The New Zealand team successfully defended the 36th America’s Cup in 2021 using an AC75 foiling monohull, beating Circolo della vela Sicilia of Italy. The New Zealand team defended its title again in 2024 beating the Royal Yacht Squadron of the UK.
Cowes Week
Cowes Week in the UK, formed in 1826, involves 40 daily races with 500 boats, 2,500 competitors in multiple divisions, and over 60,000 visitors. The race runs between the Southern English Channel and the Isle of Wight, UK. It is the largest sailing regatta of its kind in the world. The annual race will be held August 2 to 8, 2025.
Vendee Globe
The Vendee Globe yacht race in France was formed in 1989 and is held every four years. It is known as the “Everest of the seas” for its difficulty. The race is a solo single-handed non-stop, unassisted 24,000 nautical mile race round the world from France on the Atlantic, around the Cape of Good Hope, around Antarctica, around Cape Horn, and back to France. The race is open to monohull yachts conforming to the open IMOCA 60 class criteria.
In 2024-2025 there were 40 starters from 11 countries and 33 finishers. The overall winner was Charlie Dalin of France with an IMOCA 60 monohull yacht.
The Ocean Race
The Ocean Race is a round the world 40,000 nautical mile yacht race starting in Alicante, Spain and ending in different ports from October to July every 3 to 4 years. It is one of the pinnacles of yacht racing being the longest and toughest professional sporting event in the world. There are 7 to 10 competitor teams and the route has 9 to 10 stopover ports around the world. Yachts used include the Volvo Ocean 65 and the IMOCA 60 with crews of 7 to 10.
The 2022-23 race had competitor teams from the U.S., Germany, Switzerland, Lithuania, Poland, Austria, Italy, Netherlands, Mexico, Portugal, and France. The 2022-23 winner in the IMOCA 60 class was the 11th Hour Racing Team USA. The Volvo Ocean 65 class winner was the Wind Whisper Team from Poland.
Newport Bermuda
The Newport to Bermuda yacht race is one of the top classic offshore regattas formed in 1906. Annually in June 165 yachts leave Newport, Rhode Island for a 635 nautical mile race to Bermuda. There ae seven classes of races of both amateurs and professionals. In 2023 racing teams were from the U.S., England, Germany, France, Italy, Netherlands, Sweden, Canada, Bermuda, and Cayman. In 2024 the Caring USA Team won the highly coveted Lighthouse Trophy. The Pyewacket 70 USA team won the Line Honours Trophy.
Rolex Sydney to Hogart Yacht Race
An annual 630 nautical mile yacht race from Sydney, Australia to Hogart, Tasmania which was formed in 1945. It is one of the classic big offshore races and involves single mast sloops. The race is held on Boxing Day in December. There were 103 starter boats in both 2023 and 2024. Christian Beck of Australia won the Honours Trophy in both the 2023 and 2024 races with a type Juan-K 100 supermaxi.
Chicago to Mackinac
The annual 333 mile Chicago to Mackinac yacht race was formed in 1898. It is the oldest annual freshwater distance race in the world. The race is on Lake Michigan from Chicago to Mackinac Island in Lake Huron in the northern most tip of the Michigan Lower Peninsula. Over 300 boats and 3,000 sailors compete in different divisions. The 2025 race will be held July 18.
Rolex SailGP
SailGP is a biennial offshore commercial sailing series of races around the world intended to grow the sailing race audience. It was formed in 2019 by Larry Ellison. All race teams use high performance F50 foiling catamarans with the same technology to ensure the race is based on skill and not technology. The 2024-25 teams are U.S., England, France, Australia, Canada, New Zealand, Denmark, Spain, Germany, Italy, Brazil, and Switzerland. Teams compete across a season of multiple grand prix races around the world.
The reigning champion is Diego Botín‘s Spain SailGP Team, which won the 2023–24 SailGP championship.
St. Maarten Heineken Regatta
Formed in 1980, the Heineken sponsored Saint Maarten Regatta is the largest Caribbean sailing race. The annual regatta involves 8 races over 4 days with 300 boats from 37 countries. The 2025 race was held March 6 to 9, with the 2026 race to be held March 5 to 8.
Barcolana Regatta
One of the most crowded regattas with 2,689 boats, 25,000 sailors, and 250,000 spectators. Formed in 1969 the annual Barcolana race starts in Trieste, Italy for a 15 mile course in the Gulf of Trieste. There are numerous races and trophies.
Fastnet
Fastnet is a biennial British yacht race formed in 1924. It is one of the big classic offshore races. The course is a 625 nautical mile race from the Isle of Wight, rounding the southern coast of Ireland, and finishing in Cherbourg, France.
2023 winners by class:
IMOCA 60 – Charlie Dalin, Pasccal Bidegorry, France
Class 40 – Everial Team, France
Multihull – Francois Gabort, France
Monohull – Charlie Dalin, France
Hamilton Island Race
Hamilton Island race week and festival is Australia’s largest offshore sailing regatta. Formed in 1984, the race attracts over 250 teams to sail near the Whitsundy Islands in the Great Barrier Reef in northwest Australia.
Transpacific
The Transpacific is a biennial offshore yacht race over 2,225 nautical miles from California to Hawaii. The race runs on odd numbered years and attracts competitors from all over the world. Formed in 1906, it is one of the premier offshore yacht races. The race has nine different divisions and is famous for high speed downwind sailing under spinnaker in the trade winds.
The Pyewacket 70/ Roy Disney Team took the Barn Door Trophy in 2021. In 2023 the Rio 100/Moshayedi Team won.
World Match Racing Tour
The World Match Racing Tour is an annual series of professional sailor yacht races in numerous competitions over the season which was formed in 2000. A match race consists of two identical boats racing each other. The races are based on skill not technology. Race tour seven time winner British sailor Ian Williams won in both 2023 and 2024. In the 2025 races will take place in 6 U.S. cities, 7 European cities, Bermuda, Macao, and China.
Transat
Transat is a trans-Atlantic solo yacht race that is 3,500 nautical miles from France to the U.S. The race was spilt off in 2004 as a professional race from the Single Handed Trans-Atlantic Race. The race is held in June –July every four years. Competitors race in yachts with a minimum length of 40 feet. Yoann Richomme of France won the 2024 IMOCA 60 Class. Ambrogia Beccaria of Italy won the 2024 Monohulls Class 40 race.
