Most Famous Yacht Races and Luxury Regattas in the World

Whether you’re a sailor looking for your next yacht racing adventure or a spectator hoping to soak up the exclusive atmosphere of a luxury superyacht regatta, we take a look at the most famous yacht races in the world you should be keeping tabs on.

Watching one of the world’s top yacht races is how many seasoned sailors have first become interested in the sport of sailing. A display of skill, style and perseverance, significant sailing events take place in major yachting hubs around the world every month of the year. And every three to four years, yachting enthusiasts can gear up to watch extreme around-the-world regattas such as the Vendèe Globe or The Ocean Race.

The top sailing race in the world is currently considered the America’s Cup, a prestigious yacht race begun in 1851 and raced on AC75 foiling boats. But there’s also plenty of traditional sailing events to capture audiences of all inclinations, such as the Boxing Day Sydney Hobart yacht race, which involves sloops and cutters sailing along the sun-kissed shorelines of Australia, or exclusive regattas raced on luxury mega yachts, such as the St Barth’s Bucket. If you’re serious about sailing, these top sailing yacht racing events are a must-have inclusion in your calendar.

The most famous yacht races around the world

1. The Barcolana

The Barcolana, organised by the Società Velicia di Barcola e Grignano, has earned a place in The Guinness Book of World Records for being the most crowded yacht regatta in the world. Its first edition in 1969 saw only 51 sailing boats compete, but now, the annual event has grown to see more than 2,000 sail boats descend on the Gulf of Trieste every October. Boats of varying size and class, from Optimists and maxis to classic yachts, are welcomed to participate, with races accompanied by a slew of parties and events on shore.

Next edition: 8 October, 2023

2. SailGP series

A recent addition to the yachting calendar, SailGP competitions only began in 2019 but have nonetheless quickly gained popularity, with Olympic and America’s Cup sailors taking part. Created by Oracle founder Larry Ellison and champion yachtsman Russell Coutts, the SailGP regattas are raced on F50 foiling catamarans for a cash prize of US$1 million. Competitions in the series have taken place in scenic locations all over the world, from Saint Tropez and Sydney to Los Angeles, Auckland, and the UAE. Its most recent edition took place from 23 to 24 September 2023 in Taranto, Italy.

Next edition: 14-15 October 2023 (Cádiz, Spain)

3. Rolex Sydney Hobart Yacht Race

Hosted annually by the Cruising Yacht Club of Australia and the Royal Yacht Club of Tasmania, this race covers a distance of 630 nautical miles between the starting point in Sydney Harbour and the finish line in Tasmanian port Hobart. Since the first edition in 1945, The race has always started on Boxing Day and is sailed through the night. The current time record broken by LDV Comanche stands at one day, 9 hours and 15 minutes. It is considered one of the most testing yacht races in the world.

Next edition: 26 December, 2023

4. The IMA Caribbean Maxi Challenge

The IMA Caribbean Maxi Challenge comprises the three most important annual regattas in the Caribbean. The first is the RORC Caribbean 600, open to vessels nine metres and above. It is held each February in English Harbour and hosted by the Royal Ocean Racing Club and Antigua Yacht Club.

This is followed by the Sint Maarten Heineken Regatta a few weeks later, which now pulls in over 200 entrants annually and offers visitors on shore a chance to enjoy the local nightlife with accompanying daily parties and musical performances.

The ultimate winner of the Caribbean Maxi Challenge is then crowned after the event is closed off with Les Voiles de Saint-Barth April Richard Mille in April. This regatta has become one of the most respected yachting events in the Caribbean since it was first founded in 2010, and has been supported by celebrity ambassadors including Pierre Casiraghi and the late Jimmy Buffett.

Next edition: February, March & April 2024

5. St Barths Bucket

Taking place in Saint Barthélemy’s Port Gustavia, the Bucket is open to superyachts measuring over 30.5 metres. Races for yachts in the 90ft, 100ft and the Corinthian Spirit class have also been introduced in recent years. The race’s name comes from its history as a spin-off of the Nantucket Bucket, in which the winner of the first race in 1986 won a bucket as first prize in the absence of a proper trophy. The first St Barth’s Bucket was raced in 1995 with just four yachts. Since then, the race has grown in popularity and is accredited with putting the Caribbean on the map in terms of regatta racing.

Next edition: 21-24 March 2024

6. Antigua Sailing Week

Launched in 1968, Antigua Sailing Week was created by local hoteliers to encourage international tourism to the Caribbean island. It takes place every spring and is attended by around 100 sailboats ranging between seven and 30 metres. Races take place in the waters between English Harbour, Nelson’s Dockyard and Falmouth Harbour, and are accompanied by on-shore festivities including a reggae concert.

Next edition: April 27-May 3, 2024

7. The Giorgio Armani superyacht regatta

The Giorgio Armani superyacht regatta is held every June in the Italian yachting hotspot of Porto Cervo. It has always been hosted by the Yacht Club Costa Smeralda and prior to the change in sponsorship in 2021 was known as the Loro Piana Superyacht Regatta. Open only to superyachts measuring 27 metres and above, the competitive racing atmosphere on the water is complemented by glamorous parties along the coastline each night.

Next edition: June 2024

8. The Superyacht Cup Palma

Taking place every June in the waters outside the Spanish city of Palma de Mallorca, this invitation-only regatta is for sailing yachts over 24 metres. It was launched in 1996 and has now become the longest-running regatta in Europe specifically for superyachts. Between 20 and 30 superyachts normally participate, accompanied by numerous other spectators that drop anchor nearby to watch the race and enjoy on-shore parties.

Next edition: 19-20 June 2024

9. The Newport Bermuda Race

The Newport Bermuda Race takes place every two years. It started as a challenge in 1906, when Thomas Fleming Day set out to prove sceptics wrong that amateur sailors could indeed race offshore in boats smaller than 80ft. It is now considered one of the classic off-shore regattas, with the racecourse covering a 635 nautical mile stretch between the US yachting mecca of Newport and the British island of Bermuda. The race is considered a friendly and welcoming competition for new sailors, with approximately 25% of the racing boats captained by first-time skippers.

Next edition: 21 June, 2024

10. Cowes Week

Taking place in the waters of the Solent Strait around the Isle of Wight, Cowes week has been held every August since 1826. Founded by Britain’s King George IV, It is one of the longest-running regattas in the world. It is an important date in the “British social season” each summer, with royals and aristocrats still regularly making appearances. The races attract hundreds of boats and thousands of visitors, with the port town becoming a bustle of social activity during the racing.

Every other year, Cowes is preceded by the biennial Rolex Fastnet Race, an important offshore race hosted by the UK’s Royal Ocean Racing Club (RORC) and the Royal Yacht Squadron. The race is open to sailboats measuring between nine and 21 metres and follows a course that begins in Cowes and rounds Ireland’s Fastnet rock before finishing in the French town of Cherbourg.

Next edition: August 2024

11. The America’s Cup

The America’s Cup is arguably the most important event in the yachting world – perhaps even more so than the Olympic sailing competitions. First raced around the Isle of Wight in 1851, the competition was named in honour of the first winner, an iconic, US-built yacht christened America. The competition to win the “Auld Mug” trophy now takes place every three to four years in a different location. Though the race was first competed on board wooden schooners, today’s competition has evolved into a race between advanced hydrofoil vessels that can reach speeds of almost 100 km/ph.

Next edition: August – October 2024

12. The Vendée Globe

The Vendée Globe is the most extreme around-the-world race in the sailing calendar. Begun in 1989, it is known as “The Everest of the Seas” and takes place every four years. The racecourse is a global circumnavigation of just under 45,000km, beginning and ending in Vendée, France. It is sailed single-handedly by one solo helmsman on board an 18.28 metre sailboat and can take around 74 days at sea to complete. Sailors can drop anchor but are not allowed to step ashore at any point, if they wish to win the trophy.

Next edition: January 2025

13. The Ocean Race

Designed for sailboats measuring no more than 20 metres LOA, The Ocean Race is arguably one of the most well-known around-the-world sailing challenges. Formerly known as the Whitbread Round the World Race and then the Volvo Ocean Race, It has occurred every three to four years since 1973 and takes more than half a year to complete. It is a true test of perseverance, with some sections involving more than 20 days of nonstop sailing. The third leg of the race is regarded as the most difficult because sailors have to battle the treacherous conditions of the Antarctic Ocean. In 1990, the race was famously won by the all-female crew of Maiden, skippered by Tracy Edwards MBE.

Next edition: 2025

(Main image: Giorgio Armani Superyacht Regatta; Featured image: Rolex/ Carlo Borlenghi)

Frequently Asked Questions (FAQs)

– What is the most famous yacht race in the world?
The America’s Cup is the oldest and most famous yachting race in the world.

– What is the famous round the world yacht race?
The Vendèe Globe is the most famous round the world yacht race on account of the extreme requirements for entrants to sail singlehandedly, non-stop around the globe.

– What is the longest yacht participating in the Sydney to Hobart yacht race?
The yachts Andoo Comanche, Lawconnect, Wild Thing 100 and SHK Scallywag all measure 30.5 metres LOA, making them the longest yachts participating in the 2023 Sydney to Hobart race.

– What is the famous English yacht race?
The biennial Rolex Fastnet Race, which occurs around the time of Cowes Week, is the most famous yacht race taking place in English waters.