2020’s Top Winter Sun Regattas Destinations

6 December 2019
The global superyacht racing fleet of modern and classic yachts is spoilt with it’s choice of regattas and glorious destinations. The event calendar is busy, and organisers are vying for the presence of committed race goers.  
Here is a review of the top regattas to follow for Winter Sun in 2020 and why.

The Millennium Cup, New Zealand 

29 January – 1 February 2020

A warm and welcoming event set in the world’s most beautiful natural playground. Expect a small friendly fleet and lots of dolphins.  Organised and supported by the local yachting industry to encourage cruising yachts to visit the pacific and New Zealand.  Six yachts expected in 2020 including newcomers Adele and Kawil.  Anticipation high for the event in 2021 around The 36th America’s Cup.  

"We have raced the Millennium Cup multiple times with Silvertip since its first edition in 2000 and won it twice. It is always a special event which deserves much more success. Racing in the Bay of Islands surrounded by a dolphin pod playing at the bow is always a treat. The organisation is flawless, the scenery second to none and the racing quite competitive. Any superyacht cruising in the Pacific should make a point doing the Mill Cup." Owner, Silvertip. ​

Winner 2019: Tawera

Notable Entries: Freya, Janice of Wyoming, Farfalla

New in 2020/21: The J-Class Yachts have confirmed their participation in 2021 confirms Event Director Stacey Cook,  “ We are taking entries for the next two years”. 

RORC Caribbean 600, Antigua 

24 February 2020

The RORC Caribbean 600 has grown up to become a ‘must do’ offshore classic. The 600-mile race around 11 Caribbean islands is on the bucket list of any serious offshore sailor. Far from a  Caribbean cruise,  the sailing conditions can often provide thrilling racing for competitors. An increasingly popular event for the big boats. 

Winning Superyacht 2019: Nikata

Notable Entries 2020The Blue Peter the 19.65 metre classic yacht Alfred Mylne design run by British Owner Mat Barker is available for charter (6 pax).

Superyacht Challenge, Antigua

1 - 15 March 2020

We all need winter sun. The SYCA Committee was founded by locals Paul Deeth and Stan Pearson. The regatta is hosted by Admirals Inn and Antigua Rigging showing Antigua at it’s best.  An informal social program allows owners and crew to enjoy the best of the colourful local Caribbean hospitality together. Great sailing and the perfect tune-up for St Barth’s Bucket. 

Winner 2019: Nilaya
“This is a really good kick-off regatta. The sailing is important, but the fun also helps put your team together, which is good for the owners and the crew because we have a good time, and that is what it is all about.” Bouwe Bekking of Nilaya. 

Notable Entries 2020: J-Class yachts: Lionheart, Svea, Topaz, Velsheda

New in 2020: Dates have moved to be closer to St Barth’s and work better for the racing calendar. Inclusion of a “Round Antigua Race”, should conditions permit. 

St Barth’s Bucket Regatta, FWI 

19 - 22 March 2020

One for every sailors Bucket list! Fabulous trade wind racing conditions and spectacular shoreside parties with a distinctly casual island flavour make this a must-do annual superyacht regatta. For more than 30 years the Bucket as it is affectionately known, has maintained its congenial focus and non - commercial spirit. Hermes is the luxury sponsor. 

The growing Corinthian Spirit (Les Voiles Blanche), a Non-Spinnaker Class has enabled owners new to superyacht racing to experience the thrill of racing these magnificent yachts in the Caribbean for the first time.  

Winner 2019Hetarios

Notable Entries 2020 : Liara, Athos, Action and J-Class yachts: Lionheart, Svea, Topaz, Velsheda

Antigua Classic Yacht Regatta, Antigua 

1 - 7 April 2020

Run by a long-standing committee this is the largest classic yacht regatta in the Caribbean. The spirit of the event brings together everybody in the classic yacht sector from multi -million dollar schooners, modern classics, 1960’s ocean racers and local carricou sloops.  Founder Kenny Coombs said, “Everyone here is on the same level. Whether you came in flip flops or private jet, we are here for the sailing.” Make this a must-do regatta if you are serious about brass and varnish.

Notable Entries for 2020:  Elena of London, Nordwind 

New in 2020: New dates! 

Les Voiles des Saint Barth, St Barths FWI

12 - 18 April 2020

Les Voiles des Saint Barth Richard Mille as one of the fastest and largest growing regattas in the Caribbean, the 2020 edition will be it’s 12th year.  Approximately 80 yachts including Maxis and Multihulls come together in April for five days of competitive yacht racing on this beautiful island.  Event Ambassadors include sailing royalty and Monaco Prince Pierre Casiraghi.

Superyacht Winner 2019: Windfall 

Notable Entries: Sojana, Umiko 

Palma Vela Sail Racing, Palma de Mallorca

6 - 10 May 2020

Established originally to bring back Maxis to the bay of Palma (after a notable absence), the event has 14 classes and also includes ORC, TP52’s,  Classics and Dragons. Positioned early in the Spring it is proving to be a popular favourite for superyachts with serious racing teams as a Mediterranean tune-up. 

On winning The Loro Piana Superyacht Regatta in June 2019 Jochen Schümman from Magic Carpet3 , put their success down to warming up at Palma Vela. 

Loro Piana Superyacht Regatta, Porto Cervo, Sardinia

2 - 6 June 2020

An invitational superyacht regatta for yachts of 30 metres and above set in the exclusive setting of Porto Cervo.  Superyacht owners and their guests enjoy the glamorous social programme hosted by Yacht Club Costa Smeralda and fine Italian hospitality.  Longstanding luxury sponsor Loro Piana hosts an elegant owners dinner with live entertainment.   Owners love this event and sailors enjoy competitive yacht racing on La Costa Smeralda, 20 yachts competed in 2019 including a strong Wally and Southern Wind contingent.  Beautiful boats and beautiful people. 

“We have a great fleet. These boats are really tough to get around the course. To coordinate superyachts doing tacks and gybes around reefs and rocks with so many sails ……so to be racing a 50-metre yacht is a real challenge and we are having so much fun doing it. It’s absolutely fantastic to be here. We are in one of the most beautiful islands of the world, one of the most beautiful harbours and one of the most beautiful Yacht Clubs. There is nowhere better to be!”  Chris Dixon MBE America’s Cup Sailor sailing on Silencio 50-metre Perini Navi. 

Winner 2019: Magic Carpet 3

Notable Entries: Meteor, Q, Shammana, Ribelle, New in 2020: 4 scheduled race days. Introduction of a 90-99’ Class. 

The Superyacht Cup Palma de Mallorca

17 - 20 June 2020

A fun filled superyacht racing event in the Mediterranean epicentre of yachting. Three days of competitive racing and plenty of shore-side entertainment where owners, crew and sailing industry come together as one to enjoy the thriving regatta village and the best of Palma city centre. Reliable sailing conditions and summer sunshine in late June in Mallorca make this a firm favourite with 14 yachts racing in 2109. 

Winner 2019: Win-Win

Notable Entries: Velsheda, Mari Cha III, 

New in 2020: Introduction of a high-performance class. 

Newport Bermuda Race

19 June 2020

To date 125 offshore sailing yachts have committed to the 52nd Bermuda Race including classic schooner Columbia. The race is co-organised by the Cruising Club of America and The Royal Bermuda Yacht Club.

The Candy Store Cup, Newport RI

23-25th June 2020

Originally the Nantucket Bucket (and more recently the Newport Bucket) the event takes place over three days with two days of racing and lots of parties. Owned and organised by  Newport Shipyard and Bannister’s Wharf. First created for yachts that were based in the USA for the summer months it has grown to become a regular event stateside, 2019 saw 12 yachts racing from 20 to 56 metres. 2020 will be the 4th edition of The Candy Store Cup.  Expect a family friendly fleet and the glamorous appearance of Newport’s social elite fuelled by cocktails and canapes on the Top Floor of Clarke Cooke House and later in the subterranean nightclub, The Boom Boom Room.  

“We had an absolute ball all weekend,” said Clive Youlten, captain of Nakupenda. “The owner, his guests, and all of the crew onboard felt the regatta organizers did a great job keeping it fun and low-key. We were also very pleased to win our class on Day 2 and the overall series for Class B. A little extra ‘silver’ onboard never hurts!”

Winner 2019: Sirona

Notable Entries: Savannah, Zenji, Wild Horses

Maxi Yacht Rolex Cup, Porto Cervo

30 August – 5 September 2020

Organized by the Yacht Club Costa Smeralda (YCCS), in partnership with Rolex since 1985 and in conjunction with the International Maxi Association, the contest is the pinnacle of large monohull yacht racing, attracting some of the world’s best boats and the most passionate and engaged yacht owners. The fleet is divided into 8 classes: Supermaxi, Maxi Racer, Maxi Racer/ Cruiser, Mini Maxi Racer Supernikka, Lyra, Flow, and, H2O. 

Supermaxi Winner 2019: Velsheda.  

Notable Entries: Highland Fling, Lyra, Nefertiti.

Les Voiles de St Tropez

End September 2020 (New Dates TBC)

The season finale to The Mediterranean yacht racing calendar.  Modern yachts and classic yachts are split into two divisions and racing is held on separate courses. The juxtaposition of the modern Wally Yachts and the classic Schooners creates the ambiance of a true festival of sailing.  Les Voiles de St Tropez has an exhilarating social scene, one week is simply not long enough to catch up with friends, old and new. The old fishing port of St Tropez attracts the largest gathering of the world’s most beautiful classic yachts creating a photogenic spectacle and promenade for visitors. The crew parade is a hugely fun carnival like affair with a parade through the port to much fanfare and music. There is absolutely nothing stuffy about St Tropez? DO IT.      

New in 2020: Introduction of a two week-long event, the second week will be dedicated to superyachts & schooners. Watch this space.