Superyachts flock to various destinations yearly to participate in the superyacht regatta circuit. Whether eyes are on a trophy or a packed social calendar, owners can enjoy the race settings from Palma to St Barth's. With a mix of well-established classics, long-running favourites, and exciting new entries, BOAT takes a closer look at the regattas to add to your 2026 schedule, beginning in the Caribbean...
Superyacht Challenge, Antigua
March 3-8, 2026
Held annually in Nelson's Dockyard, the four-day race comprises daily pursuit races and an optional race around Antigua, with the start and finish lines just off English Harbour. Entrants are divided into three classes – buccaneers, corsairs and privateers – all competing under the ORC Superyacht Rule. Various prizes are up for grabs, including suitably filled barrels of rum. In 2025, the 37-metre Action took overall victory with the 34-metre Kawil in second place and the 45-metre Catalina in third, along with winning the Gosnell Trophy - given to the crew that has "competed in the Spirit of the Regatta", both on the water and ashore. Plenty of social events await, from beach parties to the prize-giving ceremony at Admiral's Inn.
St Barths Bucket Regatta
March 12-15, 2026
A highlight on the Caribbean racing calendar, this invitation-only event welcomes around 40 superyachts (usually upwards of 30 metres in length) to St Barth's. Entries for the 2026 edition are coming in thick and fast, including yachts like Nautor Swan's 39-metre BeCool, Royal Huisman's 65.2-metre Aquarius, and Vitters' 59-metre Maximus, to name a few. Last year, an additional "special class" (the new 100-foot racing class) was included, and 2026 will see an optional fourth day of racing. As per the last three years, social, non-racing entrants will also be welcome. Off the water, owners have their choice of countless invitations, from private gatherings to the Bucket-affiliated soiree at Tamarin and the final awards ceremony party traditionally held at the five-star Eden Rock hotel.
Read More/St Barths Bucket: The extraordinary history of an event where the ultimate aim is to win the partyGiorgio Armani Superyacht Regatta, Sardinia
May 26-30, 2026
Organised by Yacht Club Costa Smeralda, the Sardinian superyacht regatta is back for a fourth year with Giorgio Armani as its title sponsor. Last year saw 14 superyachts compete. Highlights include a Giorgio Armani Mare pop-up boutique in Piazza Azzurra, a gala dinner at the yacht club, and the return of the Southern Wind Rendezvous and Trophy. A new Corinthian Spirit division will debut this year for yachts with a cruising setup, reducing the need for professional racers on board.
Read More/Moat and Gelliceaux awarded top honours at 2025 Giorgio Armani Superyacht RegattaCyclades Cup, Antiparos
June 10-13, 2026
The Cyclades Cup is set to return for its third edition in 2026. Organised by the Yacht Club of Greece in collaboration with Ilia Rigas, World Superyacht Awards judge and owner of the 50-metre Almyra II. Held on the idyllic island of Anitparos, Greece, this second edition will welcome sailing yachts over 30 metres as well as 90-foot and 100-foot racing classes. A full social programme, including sunset cocktails, dinners, and sightseeing excursions, complements the regatta activities.
Read More/Announcing the Cyclades Cup 2026 Read more/The 2025 Cyclades Cup Superyacht Regatta: Event recapSuperyacht Cup, Palma
June 24-27, 2026
A laidback southern Mediterranean vibe prevails at the Superyacht Cup in Palma, Europe’s longest-running superyacht regatta, and for 2026, it will be a 30th anniversary edition. Uniquely, this regatta is contained within a fenced-in event village, proving that relaxed and informal can also mean ultra-exclusive. The race committee sets courses in the Bay of Palma to suit the fleet and the three classes: J, A, and B. The 24-metre Wally Rose made the headlines again in 2025, with her third Superyacht Cup Palma victory.
Read More/Six standout superyachts competing at the 2025 Superyacht Cup PalmaMaxi Yacht Rolex Cup, Sardinia
September 6-12, 2026
From iconic J Class to the newest high-performing yachts, the Maxi Yacht Rolex Cup is a highlight for many. Staged off Sardinia’s Costa Smeralda – known for its rocky scenery and turquoise waters - it continues to attract dedicated owners, highly skilled crews and exceptional yachts. The Yacht Club Costa Smeralda organisers have partnered with Rolex since the 1980s. Despite some challenging weather conditions for the 2025 edition, the race was a huge success, with Galateia taking top spot - a new Rolex IMA Maxi champion.
Swan Med Regatta-Tuscany Challenge, Marina di Scarlino, Italy
September 16-20, 2026
The Mediterranean regatta calendar is graced with the sixth edition of the Tuscany Challenge, which brings Swan owners together for a unique end-of-season event set against the stunning backdrop of the Tuscan archipelago. The Nautor Swan Experience celebrates the entire Swan community over a three-day competition. Hosted by the Yacht Club Isole di Toscana, the challenge crowns the world champions in the ClubSan 50, ClubSwan 42, and ClubSwan 36 classes.
Ibiza JoySail, Balearic Islands
September 17-20, 2026
One of the newer regattas on the Mediterranean circuit, the Ibiza JoySail regatta is returning to the Balearic Islands for its sixth edition. This laidback event welcomes maxis and superyachts for offshore and coastal racing. The 2025 event saw the veteran 35.2-metre Swan Moat dominating once again, claiming a record fifth consecutive win in the Performance Class. Registration is again invitation-only, and the regatta scene is combined with a buzzing social scene and parties aptly set on the White Island of Ibiza.
Read more/L’Hippocampe, Liberty Squared and Moat claim victory at 2025 Ibiza JoySailOyster Palma Regatta, Palma
October, 2025
Although the official 2026 dates haven’t yet been confirmed, the 19th edition of the Oyster Regatta will be held on the island of Mallorca, returning to Port Adriano. Spanning six days, the event boasts plenty of social soirees and four days of racing. The results contribute to the overall series and Oyster Cup. The 2025 event welcomed an international fleet of 20 of the British boatbuilder’s Oyster yachts on the racing roster.
Les Voiles de St Tropez
September 26 – 4 October, 2026
The Mediterranean big-boat racing season culminates with Les Voiles de Saint-Tropez, the world's largest gathering of Maxi yachts. This event is far from a small soirée, as yacht owners and crew converge to celebrate the end of summer with a week of exhilarating racing and camaraderie under the last of the summer sun. The 2025 edition had an impressive turnout with a record entry of 41 yachts.
Read More/Dates for your diary: Key superyacht events and boat shows in 2025