The World’s Most Iconic Sailing Regattas

Immerse yourself in elite sailing at these famous regattas, which transcend the boundaries of ability, endurance, and competition.

Sailing is more than just a sport—it’s a test of endurance, skill, and resilience against nature’s forces. Some regattas have achieved legendary status for their demanding courses, rich history, and world-class competition. Here are ten extraordinary sailing races that continue to captivate sailors and spectators alike.

1. The Volvo Ocean Race
Held every two to three years, The Ocean Race—formerly the Volvo Ocean Race—is widely regarded as one of the world’s most gruelling tests of endurance and skill. Spanning the globe and cutting through some of its most treacherous waters, each leg of the race lasts over 20 days, demanding unyielding resilience from its crew.

Launched in 1973-74 as the Whitbread Round the World Race, it quickly gained a reputation as one of the toughest offshore sailing challenges. With Volvo taking over as title sponsor in 2001, the race entered an era of technological advancement, introducing one-design boats to level the playing field. In 2018, it was rebranded as The Ocean Race, shifting its emphasis from corporate sponsorship to sustainability and ocean conservation.

More than a speed contest, the race is a months-long trial of strategy, teamwork, and mental and physical endurance. Crews sail identical VO65 yachts, purpose-built for strength and high performance in some of the world’s harshest marine environments.

The next edition will begin in 2027 in Alicante, Spain. The route will span the Mediterranean, plunge down the Atlantic, navigate the fierce Southern Ocean, cross the Americas, and finally return to Europe, continuing its legacy as sailing’s ultimate global challenge.

2. America’s Cup
In 1851, the schooner America defeated the British fleet in an open-water race around the Isle of Wight, giving birth to the America’s Cup—the oldest active trophy in international sport. The challenge between the New York Yacht Club and British contenders has since evolved into a global showdown for sailing supremacy.

Over the decades, the competition has been defined by fierce rivalries, groundbreaking innovation, and record-breaking performances. The America’s Cup prays on cutting-edge technology and tactical mastery, unlike most regattas. Teams pour millions into designing hydrofoil yachts that lift above the water and reach breathtaking speeds.

At the heart of the event is the coveted “Auld Mug”, a symbol of victory in one of the most elite and technologically advanced sports contests. With billionaire-backed teams, world-class crews, and national pride on the line, the America’s Cup stands as the pinnacle of competitive yachting.

3. Barcolana Regatta
As the world’s largest sailing race, the Barcolana Regatta transforms the Gulf of Trieste into a stunning display of sails. Established in 1969 with only 51 boats, the event has grown into a significant celebration of sailing, attracting over 2,000 boats and tens of thousands of sailors annually. Initially, a local competition organised by the Società Velica di Barcola e Grignano developed into a globally recognised event that merges professional competition with amateur enthusiasm. Open to sailors of all skill levels, this renowned race emphasises passion as much as expertise.

The unique format enables everyone, from experienced professionals to casual sailors, to participate in the same course. The event also showcases Trieste’s rich maritime heritage, attracting spectators from around the globe. With its high-level racing and vibrant festival atmosphere, the Barcolana Regatta symbolises inclusivity, community, and an enduring passion for sailing.

4. Rolex Fastnet Race
The Rolex Fastnet Race, one of the most demanding offshore yacht races in the world, was first held in 1925 and now takes place biennially, organised by the Royal Ocean Racing Club (RORC) in collaboration with the Royal Yacht Squadron and the City of Cherbourg. Covering 695 nautical miles, the race starts in Cowes, UK, rounds the iconic Fastnet Rock off Ireland’s southern coast, and finishes in Cherbourg, France. Known for its unpredictable weather, strong tides, and challenging navigation, the Fastnet has played a key role in advancing yacht design, safety protocols, and offshore sailing techniques.

Since 2001, Rolex has sponsored the race, which primarily focuses on monohull handicap racing under the IRC Rating Rule, awarding the prestigious Fastnet Challenge Cup to the overall winner. The event has since expanded to include multihulls one-design classes such as the Volvo Ocean Race Class, IMOCA 60s, and Class40s, along with growing interest in double-handed racing. Together with the Sydney to Hobart Yacht Race and the Newport–Bermuda Race, it is considered one of the world’s premier offshore sailing events, drawing elite professionals and passionate amateurs alike.

5. Vendee Globe Race
Popularly known as the “Everest of the Seas,” the Vendée Globe is the ultimate solo sailing challenge, pushing sailors to their physical and mental limits. Founded in 1989 by French yachtsman Philippe Jeantot—who had twice won the BOC Challenge’s 60-foot class—the race was conceived as a non-stop, unassisted, round-the-world competition in contrast to the BOC’s stopover format. Originally called The Globe Challenge, it was later renamed the Vendée Globe, after the French department that hosts the event.

The inaugural edition in 1989–90 was won by Titouan Lamazou, with Jeantot finishing fourth. Since 1992–93, the race has been held every four years, drawing elite sailors from around the world. Competitors must navigate treacherous waters, from the storm-lashed Southern Ocean to the icy fringes of Antarctica, relying solely on their skill, endurance, and strategic judgment. With no outside assistance allowed, simply finishing the Vendée Globe is considered one of sailing’s greatest achievements.

The race has played a pivotal role in advancing the design and performance of IMOCA 60 yachts, fostering innovations that continue to shape offshore sailing. For those who dare take it on, the Vendée Globe is not just a race—it is a solitary battle against the sea, the elements, and one’s own limits.

6. Transpac Race
The Transpac Race, one of the most esteemed offshore races in the Pacific, spans 2,225 nautical miles from Los Angeles to Honolulu. Established in 1906, this biennial event is renowned for its thrilling downwind sailing and stunning open-ocean vistas. Crews must balance speed and navigation as they harness the Pacific trade winds to reach the finish line in Hawaii. The blend of history, challenge, and natural beauty makes the Transpac a preferred choice among offshore sailing aficionados.

7. Rolex Middle Sea Race
The Rolex Middle Sea Race, a Mediterranean classic, is an exhilarating offshore regatta that commences and concludes in Malta. This 606-nautical-mile course navigates around Sicily, passes the active volcano Stromboli, and showcases the stunning landscapes of the Mediterranean. Renowned for its sudden changes in weather from tranquil waters to severe storms, the race challenges competitors to demonstrate strategic excellence. With its rich heritage and magnificent setting, the Rolex Middle Sea Race ranks among the most visually striking regattas globally.

8. Around the Island Race
The Around the Island Race, held off the Isle of Wight, commemorates British sailing. This event attracts many boats, from professionals to weekend warriors, with over 1,500 boats competing yearly. With its challenging tidal patterns and changing winds, the 50-nautical-mile route presents breathtaking coastline views. One of the most well-known sailing events in the UK, it draws spectators and contestants, thanks partly to its inclusive character and energetic ambience.

9. Cowes Week
One of the oldest and most well-known sailing regattas globally, Cowes Week is steeped in history and prestige. First established in 1826, this British establishment draws over 100,000 spectators and many sailors yearly. Cowes Week is a major social occasion with various races, from sophisticated yachts to conventional sailing boats. The shoreside festivities and famous fireworks’ show set the European sailing season apart.

10. Cape2Rio Yacht Series

The longest continent-to-continent yacht race in the southern hemisphere, the Cape2Rio Yacht Race, provides a magnificent transatlantic experience. This competition, spanning over 3,600 nautical miles from Cape Town, South Africa, to Rio de Janeiro, Brazil, is a real challenge of tactics, seamanship, and endurance. Contestants must manoeuvre the Atlantic Ocean, confront long stretches of solitude, and endure erratic weather patterns. For offshore sailors looking for the ultimate adventure, the difficulty of crossing an entire ocean makes Cape2Rio a bucket-list event.