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For seasoned yachties and newbies alike, attending a sailing regatta is one of the true highlights of the yachting calendar. Here, we present everything you need to know about the top regattas all around the world, with some hints and tips from industry experts on how to make the most of every minute.&nbsp;Maxi Yacht Rolex Cup (3-9 September 2023)Returning for its 33rd edition in 2023, the <a data-gid="gid://syiq/Event/179" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Maxi Yacht Rolex Cup - 2023">Maxi Yacht Rolex Cup</a> is a racing-orientated event, with the very best of the racing community found on board – from young sailors keen to bank experience on these racing machines to Olympic medalists and world champions.From the historical J Class to the newest high-performance yachts, since its first inception in 1980, the industry’s most talented sailors have gathered together amidst the rocky scenery and turquoise waters of Costa Smeralda to compete at the highest levels, with a record 50-strong fleet participating last year.There will be a key difference in this year’s edition, as <a data-gid="gid://syiq/Company/2826" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Yacht Club Costa Smeralda (Company)">YCCS</a> Sports Director Edoardo Recchi highlights: “For the first time ever, we will also have a multihull division. We are very excited about having a new kind of racer at the<a data-gid="gid://syiq/Event/179" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Maxi Yacht Rolex Cup - 2023">&nbsp;Maxi Yacht Rolex Cup</a>. <a data-gid="gid://syiq/Company/2826" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Yacht Club Costa Smeralda (Company)">Yacht Club Costa Smeralda</a> has always paid attention to the evolution of the sail racing world and this opening up to multihulls proves it.”<img src="https://photo-assets.superyachttimes.com/photo/47186/image/large-7bda43b55596ed4eaf29bbf627b70726.jpg" data-gid="gid://syiq/Photo/47186">Monaco Classic Week (13-16 September 2023)La Belle Classe biennial event hosted by the <a data-gid="gid://syiq/Company/4337" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Yacht Club de Monaco (Company)">Monaco Yacht Club</a> is a gathering that celebrates both sailing and motor yachts from 12-foot to 80-metres. The event echoes the first motorboat meetings in 1904, this event is the only one to bring together the most beautiful traditional sailing boats, with vintage motor-yachts and old motorboats, to which a fleet of 12′ Dinghies has been added for four the last editions.In every edition of the event, classic yachts such as Mariella, <a data-gid="gid://syiq/Yacht/2103" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Puritan38.4m (125'12&quot;)Electric Boat1931">Puritan</a>, <a data-gid="gid://syiq/Yacht/11294" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Orianda 25.9m (84'12&quot;)J. Ring Andersen Skibsvaerft1937">Orianda</a> and <a data-gid="gid://syiq/Yacht/2093" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Invader49.3m (161'9&quot;)Lawley1905">Invader</a>&nbsp;parry in front of Monaco Marina, while the smaller motor boat classes shoot through the waves. The event is a true celebration of all yachts classic and is a great opportunity to see a spectrum of beautifully restored boats.&nbsp;Les Régates Royales Cannes (24-30 September 2023)Founded in the mid-1800s, the yachting heritage of Cannes is one of the oldest in the Mediterranean and every September the tiny seaside town plays host to a spectacle of sailing yachts of all classes and ages.&nbsp;A week of regattas off the Lerins Islands for a fleet divided into eight categories according to the size, age and rigging of the yachts. An exceptional gathering as the largest and most famous yachts of the last century and before come to compete such as the majestic <a data-gid="gid://syiq/Yacht/3188" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Elena of London55.0m (180'5&quot;)Factoria Naval Marin2009">Elena of London</a>, 55-metre, <a data-gid="gid://syiq/Company/829" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Herreshoff (Company)">Nathanaël Herreshoff</a> design built in 2009, <a data-gid="gid://syiq/Yacht/1818" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Cambria41.15m (135'0&quot;)William Fife & Sons1928">Cambria</a>, 41-metre, <a data-gid="gid://syiq/Company/1109" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="William Fife & Sons (Company)">William Fife</a> design built in 1928, <a data-gid="gid://syiq/Yacht/2343" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Sunshine36.85m (120'11&quot;)Myanmar Shipyards2003">Sunshine</a> 36.85-metre, <a data-gid="gid://syiq/Company/1110" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="William Fife (Company)">William Fife</a> design built in 2003, <a data-gid="gid://syiq/Yacht/2101" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Aschanti IV of Vegesack34.8m (114'2&quot;)Burmester1954">Aschanti IV of Vegesack</a> 34.67-metre, <a data-gid="gid://syiq/Company/1232" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Henry Gruber (Company)">Henry Gruber</a> design built in 1954, the <a data-gid="gid://syiq/Yacht/1864" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Moonbeam of Fife III30.94m (101'6&quot;)William Fife & Sons1903">Moonbeam of Fife III</a> 30.94-metre, <a data-gid="gid://syiq/Company/1109" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="William Fife & Sons (Company)">William Fife</a> design built in 1903 and <a data-gid="gid://syiq/Yacht/2342" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Moonbeam IV32.1m (105'4&quot;)William Fife & Sons1920">Moonbeam IV</a>, 32.1-metre, <a data-gid="gid://syiq/Company/1109" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="William Fife & Sons (Company)">William Fife</a> design built in 1914. The event should be on the list for any sailing enthusiast and the town of Cannes is a wonderful base for this historic regatta.<img src="https://photo-assets.superyachttimes.com/photo/283380/image/large-e434ea0edef7ecf9fc716834cdfdbfae.jpg" data-gid="gid://syiq/Photo/283380">Les Voiles de St Tropez (1-7 October 2023) Drawing the Mediterranean superyacht racing season to a suitably fabulous conclusion is the enduringly-popular and prestigious Les Voiles de Saint-Tropez, representing one of the largest gatherings of Maxi yachts in the world.The event is a yacht-spotter’s paradise, as Pierre Roison, President of the Société Nautique de Saint-Tropez, organizer of the event, highlights: “Every year, there are new boats to discover or to rediscover at Les Voiles. Last year saw the return of the extraordinary 1902 three-masted yacht <a data-gid="gid://syiq/Yacht/2266" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="Shenandoah of Sark55.08m (180'9&quot;)Townsend & Downey1902">Shenandoah of Sark</a>, which is 55.08-metres long and belonged to Baron Bich, who used it as his flagship to attend the regattas when he was competing in America’s Cup.”He continues: “Saint-Tropez is the only place in France where you can see the futuristic Wally yachts in action. Another example, we were privileged to see the cutting-edge maxi Flying Nikka, a 19-metre articulated foiler built by an Italian team and designed to exceed 40 knots at top speed.”Superyacht Challenge Antigua (March 2024) Serving as a welcome kick-off to the regatta season each year is the Superyacht Challenge Antigua. Held annually in the UNESCO World Heritage Site of Nelson’s Dockyard, the race begins and ends just off English Harbour and is made up of daily pursuit races, as well as an optional race around the island.Famous for its laid-back atmosphere, those competing in the Superyacht Challenge Antigua are divided into three classes (buccaneers, corsairs and privateers) and are awarded Caribbean barrels of rum for their successes. <img src="https://photo-assets.superyachttimes.com/photo/219539/image/large-eda4015f563d6bef20bdd258c92d9401.jpeg" data-gid="gid://syiq/Photo/219539">The Superyacht Challenge Antigua is the perfect event for racing newbies, as Co-founder Paul Deeth explains: “You will find great racing in a relaxed and friendly setting which is ideal for owners experiencing superyacht racing for the first time. We offer a superyacht ‘classic’ class, which means yachts can race with their standard sails and do not need a lot of extra crew, which helps to keep the pressure off.”<a data-gid="gid://syiq/Event/199" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="St. Barths Bucket Regatta - 2024">St Barths Bucket Regatta</a>&nbsp;(March 2024)&nbsp;Distinctive for its sheer number of superyacht entries, the regatta calendar would not be complete without mention of the <a data-gid="gid://syiq/Event/199" href="#managed-by-system" rel="noopener noreferrer" target="_blank" title="St. Barths Bucket Regatta - 2024">St Barths Bucket</a>, which sees as many as 35 superyachts of all shapes and sizes descending on the Caribbean island to enjoy nail-biting racing in a beautifully picturesque setting.The Bucket is also known for its top-notch social programme, with six of the 31 entries this year being social ones, in which yacht owners and guests can make the most of the recreational aspects of the Bucket without racing – whether that is the Bucket’s shoreside parties, spectacular local beaches or world-renowned shopping and restaurants.<img src="https://photo-assets.superyachttimes.com/photo/283379/image/large-c1d8a0d7d9c638a74da544c6b067a788.jpg" data-gid="gid://syiq/Photo/283379">Due to its popularity, it is worth planning your travels to the Bucket well ahead of time, as Peter Craig, Event Director and Race Chairman highlights: “Whether you are racing or race viewing, you need to plan well in advance. Our local businesses claim that ‘Bucket Week’ is the busiest of the year – and that includes Christmas and New Year, so it is important to be very organised when booking accommodation.”Les Voiles de St Barth Richard Mille (April 2024) Despite being a relatively new addition to the racing scene, Les Voiles de St Barth Richard Mille is on the bucket list of many seasoned sailors, thanks to its blend of intense island racing and incredible scenery with a fantastic après sailing atmosphere. Come for the racing, stay for the nightlife, as event organiser and co-founder François Tolède explains: “Every evening the race village vibrates with incredible concerts and projections of the day's races on a massive screen. We also have our famous crew party which brings together more than 1,000 guests for a huge laser show, food, a bar, music, DJs and much more.”This article is featured in the 45th edition of the SuperYacht Times newspaper.&nbsp;<a href="https://shop.superyachttimes.com/report/the-superyacht-times-subscription" rel="noopener noreferrer" target="_blank" title="">Subscribe now</a>&nbsp;to receive your copy straight to your door and never miss another issue.

How to prepare for a regatta

Georgia Tindale takes a deep dive into the 2023/2024 regatta calendar to share expert insight into the most exciting weeks of the year.

Wind in your sails: Preparing for the upcoming regatta calendar 