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Top 10 Famous Sailing Races of the World

  • Writer: Editor
    Editor
  • Sep 7
  • 5 min read

September 2025


Some sailing races are so iconic that even people who’ve never set foot on a boat have heard of them. For us cruisers, they’re more than headlines or spectacular drone shots — they’re reminders of just how far boats (and the people who sail them) can go when tested by the sea.


These events carry decades of history, incredible human stories, and plenty of innovation. The gear we rely on today — from stronger sails to better autopilots — often started out in races like these, pushed to breaking point by sailors willing to risk it all.


So let’s take a look at ten of the most famous sailing races in the world, and why they continue to inspire everyone who loves life at sea.


1. The Vendée Globe — the “Everest of the Seas”


If you’ve ever heard of a sailor disappearing into the Southern Ocean for months and coming back a legend, chances are it was the Vendée Globe. It’s a solo, non-stop, unassisted lap of the planet that’s been run every four years since 1989. Only a handful of people have ever finished it, and every edition brings stories of broken masts, incredible rescues, and sheer human stubbornness.


The next Vendée kicks off in 2028 — and yes, I’m already excited to follow the tracker.



IMOCA racing yacht battling waves during the Vendée Globe

2. The Golden Globe Race — a step back in time


Imagine sailing around the world without GPS, GRIB files, or modern autopilots. That’s the Golden Globe Race — a tribute to the original 1968 race that made Robin Knox-Johnston the first person to sail solo non-stop around the world. The rules force sailors to use old-school boats and celestial navigation.


The next one sets off in September 2026 from Les Sables d’Olonne. It’s not about speed — it’s about endurance, patience, and a good sense of humor when you’re alone with a sextant for months.



3. The Ocean Race — teamwork at its limit


If the Vendée is all about being alone, The Ocean Race (formerly the Volvo Ocean Race, and before that the Whitbread) is the opposite. Teams of hardened pros race one-design foiling boats around the world, swapping watches in brutal conditions. Since 1973, this fully crewed circumnavigation has been one of the hardest team sporting events on Earth.


The next lap of the globe is set for January 2027, but right now (2025) we’re watching the Ocean Race Europe, which gives us a taste of the same intensity closer to home.


Read more: The Ocean Race


4. The Rolex Fastnet Race — tides, tactics, and history


First held in 1925, the Fastnet is an offshore rite of passage. It runs from Cowes, across the English Channel, out around the Fastnet Rock off Ireland, and finishes now in Cherbourg. It’s about 695 miles of tides, traffic, and weather systems all colliding.


It’s also where amateurs and pros line up together — and that’s part of its magic. Every odd-numbered year, thousands of sailors dream of rounding the Fastnet Rock and seeing that lighthouse in the spray.


Official site: The Rolex Fastnet Race


5. The Rolex Middle Sea Race — a lap around Sicily


If the Fastnet is grey seas and cold spray, the Middle Sea Race is its Mediterranean cousin — a lap around Sicily starting from the dramatic Grand Harbour of Valletta, Malta. You race past volcanoes (yes, Stromboli often glowing at night), down the Strait of Messina, and across blue water that can be deceptively calm… until it isn’t.


It runs every October, and if you ever anchor near Malta at that time, it’s worth seeing the start: cannons firing, sails filling, and the whole fleet funnelling out of one of the most beautiful harbours in the world.



Grand Harbour, Valletta filled with sails at the Rolex Middle Sea Race start

6. The Rolex Sydney Hobart — Boxing Day tradition


Every December 26th, while much of the world is still digesting Christmas dinner, the Australians (and plenty of internationals) launch into the Sydney Hobart. From Sydney Harbour down to Hobart, Tasmania, it’s 628 miles that include the infamous Bass Strait — a stretch of water that can serve up anything from flat calm to survival storms.


It’s been running since 1945, and is broadcast live across Australia. For sailors, it’s both a challenge and a celebration. The 2025 race will be the 80th edition.



Fleet of yachts charging out of Sydney Harbour at the start of the Rolex Sydney Hobart Yacht Race

7. The Route du Rhum — the sprint across the Atlantic


If the Vendée Globe is the long game, the Route du Rhum is a drag race. Solo skippers blast from Saint-Malo in France to Guadeloupe, covering about 3,500 miles. It only runs every four years, but when it does, France practically shuts down to watch.


The fastest Ultim trimarans make it across in just over a week — insane speeds for a solo sailor. The next edition is in November 2026.


Official site: The Route du Rhum


8. The Transat Jacques Vabre — the double-handed challenge


Also called the “Coffee Route,” this race pairs two sailors per boat for an Atlantic crossing from Le Havre to the Caribbean. First run in 1993, it’s become the training ground for Vendée hopefuls and a benchmark for partnership at sea.


The next one starts October 2025. Expect sleep-deprived sailors, endless freeze-dried meals, and some of the fastest transatlantic passages ever.



9. The Mini Transat — little boats, big dreams


Picture sailing solo across the Atlantic… in a 6.50 meter boat. That’s the Mini Transat. Since 1977, this race has launched the careers of many Vendée skippers and pushed innovation in small-boat design.


The next one begins in September 2025, and it’s always one of the most inspiring races to follow — a reminder that you don’t need a huge boat to chase huge dreams.


Read more: The Mini Transat


10. The America’s Cup — where design meets spectacle


And then there’s the America’s Cup — the oldest trophy in sport. First raced in 1851, it’s now a high-speed, foiling, design-driven arms race between nations. The last edition lit up Barcelona in 2024, with Emirates Team New Zealand defending.


The next one? 2027 in Naples, Italy. Expect national pride, technology on the bleeding edge, and TV coverage that even non-sailors can’t look away from.


Why do these races matter to us cruisers?


Because they remind us what’s possible. Whether it’s a 20-year-old in a Mini crossing alone, a team screaming downwind at 40 knots, or a retro sailor shooting the stars with a sextant, these races show the many ways the sea tests us.


And in a quieter way, they influence our world too. The lithium batteries, the autopilots, the sails, the satellite comms — all got better thanks to the people pushing them to breaking point in these races.


FAQs: Famous Sailing Races


Which famous races happen every year?

The Sydney Hobart and the Middle Sea Race run annually.


Which ones are solo circumnavigations?

The Vendée Globe and the Golden Globe.


What’s the best entry-level “big race”?

Many cruisers aim for the Fastnet or Middle Sea — still tough, but achievable with training.


These races aren’t just about trophies or records. They’re about courage, endurance, and that restless need sailors have to see what lies beyond the horizon. Whether it’s a solo skipper rounding Cape Horn, a crew battling the Bass Strait, or a fleet charging out of Valletta to cannon fire, each race carries a piece of the sea’s timeless story.


For us cruisers, following them is a way to dream bigger, to learn a little, and sometimes to imagine ourselves out there — sails full, heart racing, chasing the same wind.


⚓ Which of these races would you love to witness in person — or maybe even one day join?


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