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The 5 Most Exciting Sailing Races in the World

In life, as with motorsports and sailing sports, the exhilaration of speed reaches a fever pitch when paired with humanity’s desire to push the envelope. For those who engage in the thrill of sailing sports or simply harbor aspirations to partake of it, these are 5 of the most exciting sailing races in the world to explore. 

For those who are inclined towards the thrill and adventure of the open seas, there is nothing to rival the bracing winds, the invigorating sunlight, and the vast mysteries of an endless horizon. The trials of sailing and sportsmanship simply add to the excitement of it all, proffering a competitive element that many seamen yearn to conquer in their quest to ascend to the pinnacle of the sport. 

While it is certainly a worthwhile endeavor to participate in a sailing race, the fledgling sailor may not have the necessary knowledge to make the most of the experience. However, there is much to be learned by simply observing seasoned seamen in their element, with an abundance of talent, skill, strategy, style, and perseverance on display. 

Beyond the adrenaline rush they provide, sailing races spotlight the fortitude of man against nature. From trying weather conditions and rocky tides to the mental resilience required to overcome challenges in competition, success depends on more than just the vessel. Here, man, machine, and ocean come together in a spectacular display to inspire and entertain, garnering well-deserved attention from yachting enthusiasts the world over. 

While the first sailing race is believed to have been held in 17th century Netherlands, the sport has since grown by leaps and bounds. Most notably, the continued advancement of technology has opened doors for a new breed of sailors to conquer the vast oceans, leaving an indelible mark on the sport as it stands today. The development of new cutting-edge materials and methods has paved the way to better vessels, improving speed and durability. Additionally, sophisticated navigation systems and precision-engineered sails have all contributed significantly to modern yachting, transforming the way that sailors approach their craft and pushing the boundaries of speed and performance to hitherto unprecedented levels.  

While the winds of change undoubtedly continue to shape the landscape of yacht racing, there is but one constant: the enduring spirit of adventure shared among sailors and spectators alike. With an abundance of sailing races that occupy each calendar year, yachting enthusiasts are spoilt for choice in the competitive arena. From the prestigious America’s Cup to the thrilling Rolex Fastnet Race, let’s dive into five of the most exciting sailing races in the world. 

5 of the most exciting sailing races in the world 

America’s Cup

Americas Cup
The most important yachting event in the world, the America’s Cup prioritizes technological advancements and innovation. (Image: America’s Cup/Instagram)

The oldest and most revered of international sailing races, the America’s Cup enjoys its prime position as the most important event in the yachting world. Comparable to Formula 1 in the realm of motorsports, the America’s Cup boasts a long and storied history that began in 1851, when the yacht ‘America’ won a race around England’s Isle of Wight, solidly defeating a fleet of British wooden schooners. In honor of the winning yacht, the trophy was officially renamed The America’s Cup, with the competition now held every three to four years across the world in waters that proffer challenging sailing conditions for the ultimate test. 

Due to its prestige, the America’s Cup easily attracts attention, most notably from top professional sailors, yacht designers, and high-profile sponsors spanning businesses and entrepreneurs alike. Beyond the skill of its sailors, the competition emphasizes advancements in sail design, with competitors often leveraging technology and innovation to push the boundaries in seeking success. Many teams invest a significant portion of their resources into designing and building state-of-the-art yachts, incorporating cutting-edge materials, aerodynamics, and navigational systems that contribute to their odds for victory. Today’s visitors and viewers can expect extraordinary races between advanced hydrofoil vessels known to reach speeds of 100 km per hour.  

Next edition: August – October 2024 

Ocean Race

exciting sailing races
The Ocean Race typically takes up to nine months to complete, and is one of the most challenging but exciting sailing races in the world. (Image: The Ocean Race/Instagram)

Since its very first iteration in 1973, the Ocean Race has taken place once every three years. While it began life as the Whitbread Round the World Race, it was eventually renamed the Volvo Ocean Race in 2001 when Volvo became its main sponsor. In 2018, it assumed its current form as the Ocean Race, spotlighting the organizers’ new direction which emphasizes sustainability and environmental awareness. Designed for sailboats that measure no more than 20 meters LOA, the Ocean Race is one of the longest and most challenging sailing races worldwide, taking up to nine months to complete. 

Competitors consist of professional sailors, each participating under the banner of a key sponsor, which can range from corporations to countries. These sponsors provide funding for boat design, technology, and personnel training in the hopes of gaining a competitive edge. Typically kicking off in Europe, the race brings teams around the globe, with stops at designated ports in different continents along the way. Teams must battle the freezing temperatures of the Southern Ocean as well as the intense muggy heat of the equator, enduring extremities and navigating rough seas, strong winds, and unpredictable weather in the process, making for a truly exhilarating experience indeed.  

Next edition: August 10 2025 

Barcolana Regatta

exciting sailing races
The Barcolana Regatta sees thousands of participants annually, and is a mass-start event. (Image: Barcolana Regatta/Instagram)

With origins dating back to 1969, the Barcolana Regatta first began life as a friendly race between a group of friends to mark the end of the sailing season, with just 51 vessels competing in its inaugural event. However, it has since expanded over the years, and today commands the attention of yachting enthusiasts the world over, with 25,000 sailors and ten times that in spectators. Organized by the Società Velicia di Barcola e Grignano and held in Italy’s Gulf of Trieste every October, the event hosts boats of all shapes and sizes. It also holds a place in The Guinness Book of World Records for being the most crowded yacht regatta in the world. 

The highly competitive sailing race boasts a unique format, being a mass-start event where all participants begin simultaneously, regardless of size or class. Covering about 15 nautical miles that take participants along the scenic coastline of Trieste, the race is an excellent showcase of sailboats and skill, a worthy addition to any sailing calendar. 

Next edition: October 13 2024 

Vendée Globe

exciting sailing races
A solo endeavor, the Vendée Globe race is one of the most exciting, thrilling, and yet challenging sailing races in the world to embark on. (Image: Vendée Globe/Instagram)

A solo endeavor where victory greatly depends on mental fortitude, the Vendée Globe is considered one of the most challenging, extreme, and prestigious sailing races in the world. First held in 1989, the race begins and ends in Les Sables-d’Olonne, a seaside town in the Vendée region of France; it is for this region that the race is named. Held every four years, the journey is an incredible commitment that takes over three months to complete. 

Covering approximately 24,000 nautical miles, the race brings sailors through some of the most treacherous and remote waters on the planet. This includes the Southern Ocean, where extreme weather conditions, towering waves, fierce storms, and icebergs provide a test of one’s mettle. In a true test of skill in every measure of the word, all sailors must navigate, sail, repair, and manage the journey completely solo. The extreme isolation faced by the solo sailors can often prove too difficult for even the most seasoned of seafarers; as such, even completing the race is no small feat. 

Next edition: November 10 2024 

Rolex Fastnet Race

Rolex Fastnet race
The Rolex Fastnet race is one of the most exciting sailing races in the world, rounding the Fastnet Rock off Southern Ireland. (Image: Rolex Fastnet Race/Instagram)

With a rich history dating back to 1925, the Rolex Fastnet Race is a biennial offshore yacht race widely acknowledged as one of the most prestigious and challenging yacht races in the world. Organized by the UK’s Royal Ocean Racing Club (RORC) alongside the Royal Yacht Squadron in Cowes and the City of Cherbourg in France, the race is named for the Fastnet Rock. The rock in question is an iconic feature located 6.4 kilometers off the cost of County Cork in the South of Ireland that the racecourse famously rounds. 

Given the treacherous ocean terrains that incorporate busy shipping lanes, strong tidal currents, and the potential of hazardous weather, the race is a true test of skill, navigation, and determination. While the race generally takes several days to complete, the most talented of sailors have completed it in as few as two to three days. Open to professional and amateur sailors with a vast range of yachts in competition across various classes, the race presents an admirable challenge to all who wish to test their mettle at the esteemed sport. 

Next edition: July 26 2025

(Main and featured images: Barcolana Regatta/Instagram)