At the mercy of Mother Nature, powered only by an ever-changing wind (motorboats aren't allowed here) sailors fight to outmanoeuvre one another (and avoid going overboard in the process) to cross a finish line that moves with the waves.
It's what makes sailing competitions such a thrilling spectator sport — and that's before you even get to the after-parties.
But which to attend? A regatta is a series of races held over several days; competitors earn points in each race, and the lowest overall score usually wins. Fleet races see dozens (and sometimes hundreds) of boats start together, battling around marked buoys before crossing the finish line.
Match racing (like the famed America’s Cup) pits one boat directly against another, making tactics and strategy as important as speed. Offshore and ocean races see competitors covering large distances that can last days, weeks, or months – and take the most dedicated spectators around the world with them.
From head-turning superyachts in Italy or pre-war classics contending with Scotland’s notoriously interchangeable weather, here’s all you need to know about the biggest sailing competitions around the world.
Sailing competitions across the globe
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America’s Cup
Perhaps the most revered of the lot, the America’s Cup dates back to 1851 and is the oldest international sporting trophy in the world. Its prestige draws a crowd of the same ilk – Prince Albert II of Monaco and King Charles III have attended; Larry Ellison owned the successful Oracle Team USA and helped modernize the event with foiling catamarans.
While there’s talk of the 2026 America’s Cup, the main event won’t actually take place until 2027 in Naples, Italy. This year sees the competing teams race in smaller regattas using high-speed foiling boats to test their crews and equipment (and their mettle). The first regatta, held in Cagliari, Sardinia, saw Luna Rossa Prada Pirelli (Italy) win on home waters, beating Emirates Team New Zealand in the final. GB1 (Great Britain), led by Sir Ben Ainslie (the most successful sailor in Olympic history), faced some technical difficulties in the event, but recovered with a strong and impressive pace when the boat was in working order. Italy are considered the ones to watch for the 2027 main event, where they’ll have huge home support when the race returns to Naples.
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Maxi Yacht Rolex Club
The brainchild of the Yacht Club Costa Smeralda and its president, Aga Khan IV, the first Maxi Yacht Rolex Cup (then known as the Maxi World championship) was held in Sardinia in 1980. Rolex got onboard in 1985 and began sponsoring the event, and has been doing so ever since. Some of the most technologically advanced (read: expensive) yachts race, and each one must be at least 60-ft (18.3-meters) long, but some reach 140 ft (43 meters).
Some of the most recognizable yachts have competed — Velsheda, the only original J Class yacht to win in Porto Cervo, famous for her classic 1930s lines and massive 185-tonne displacement, has nabbed overall class victories in 2013, 2016, 2019, and 2021. The 100-ft Leopard 3, a super-maxi designed by Farr in 2007, underwent a huge refit to shed around 10 tonnes, and then won in 2024 — dominating the event.
The course goes beyond laps as competitors navigate tricky coastal courses around the La Maddalena Archipelago. The waters here are infamous for unpredictable winds, rocky islands, and narrow channels – so tactics are everything. The fastest classes also race on traditional windward-leeward courses, where boats repeatedly sail into and away from the wind. The event usually takes place in September, on the first or second week of the month.
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Les Voiles de Saint-Tropez
A successor to the famed Nioulargue regatta, Les Voiles de Saint-Tropez began in 1999 and, in its 26-ish-year lifespan, its brought an impressive mix of classic wooden yachts, hi-tech racing yachts, and enormous maxi yachts to the Gulf of Saint-Tropez. It’s often considered the most photogenic event because of the contrast of historic yachts against modern counterparts (plus, the backdrop of the French Riviera is obviously quite pretty).
It’s probably one of the regattas with a more lively atmosphere, with spectators and crews filling the harbor – and celebrations stretching into the evenings. Public access is free around the harbor, but spectators often watch from the nearby beaches (or from a boat to get really close). The event will run from September 26 - October 4, and this year’s headline act is the return of the J Class. These elegant 1930s-esque yachts are adored for both their form and function, and this year will see three J Class yachts racing together, the Svea, Rainbow, and the Hanuman.
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Rolex Swan Cup
Every two years since 1989, a fleet of Swans has gathered at the Yacht Club Costa Smeralda in Sardinia. Unlike other regattas, this one celebrates a single yacht builder: the Swan and the Swan only. This year, the 23rd edition of the event and the 60th anniversary of the Nautor Swan, will see a record fleet of over 120 taking part. Leading the way is the Tarantella, aka hull number one, the very first Swan ever built in 1966. Following a meticulous refit, she will return to the starting line of the cup. This year’s line-up is yet to be finalized, but a few others to keep an eye out for are Swan Maxis (the largest in the fleet) and the Sparkman & Stephens-designed classics from the 1960s and ‘70s.
See more: Superyacht Launches to Have on Your Radar for 2026
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Richard Mille Cup
A new kid on the block, in racing terms at least, the RM cup was founded by the watchmaker and Classic Regattas Ltd in 2022. It skews exhibition sailing and favors long offshore and coastal passages – the first editions were held along England’s south coast, racing from Falmouth to Dartmouth, Cowes, and Le Havre. This year’s was in Scotland’s Firth of Clyde – the course included The Isle of Arran and The Cumbrae Islands, areas known for fast-changing weather and mighty tides. Entry is invite-only and yachts must reach a certain criteria – built before 1939 or modern replicas built to original plans. The trophy is especially coveted; made by Garrard, the oldest jewelry house in the world, it stands just over three-feet tall and is made from sterling silver.
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Giorgio Armani Superyacht Regatta
Usually held in late May, the Giorgio Armani Superyacht Regatta marks the start of the Mediterranean racing calendar — along with a suitably glam social calendar. The event takes place in Porto Cervo, Italy, and yachts need to measure at least 80 ft and multihulls at least 50 ft. Hosted by the Yacht Club Smeralda, this year’s race marked the 20th edition and saw 17 superyachts tackle the waters of La Maddalena channel. The fleet was split into Blue and White classes, based on the yachts’ performance and ratings under the Offshore Racing Congress Superyacht (ORCsy) handicap. The winner in the Blue Class was the 106.6-ft Swan 115 Moat; the White Class winner was the 102.5-ft Southern Wind 96 Liberty Squared.
