Races and Regattas Calendar 2019

Races and Regattas Calendar

Races and Regattas Calendar 2019 

Our list of some of the most popular international yachting events. We hope you will be inspired to participate in these amazing races. Charter a regatta sailing yacht or a luxury spectator yacht in whatever destination you choose. Charter friends and families will discover the thrill of competition, fabulous parties, great camaraderie and loads of fun.

Races and Regattas Calendar

January 16-24, 2019 Mount Gay Rum Round Barbados Sailing Race

The first organized race around Barbados was held on January 1st 1936 when 5 trading schooners competed for ‘bragging rights’ and a small prize. The winner was Lou Kennedy’s Sea Fox in a time of 10 hours and 20 minutes. Those fierce competitors could never imagine the high-tech, super-skilled racing yachts and teams of today.

Races and Regattas Calendar

Three days of coastal races and regattas can be entered separately, or together with the Mount Gay Round Barbados Race. Racing is in 5 classes on both the South and West Coasts of the Island. On shore, a party nightly allows teams to relax, unwind, discuss the following days tactics… or just have a glass or two of Mount Gay Rum. Trade winds and incredible sailing conditions make this a challenging 70 mile course.

January 28-February 2, 2019 Grenada Sailing Week

Participants begin with the famous Welcome Party and Skippers Briefing … meet old friends and new, drink Mount Gay Rum and brag about races and regattas past, listen to talented local bands entertaining you until the early hours.

January 30-February 3, 2019 NZ Millennium Cup, Bay of Islands, Bay of Islands, New Zealand

Races and Regattas

New Zealand offers high-quality racing, exceptional hospitality and the picturesque scenery of the Bay of Islands. The NZ Millennium Cup launches the South Pacific’s 2019 regatta season. A new format accommodates a larger fleet to race on a challenging course. Race organizers anticipate a surge of interest due to the upcoming America’s Cup, set to take place in New Zealand in March 2021.

NZ Millenium Cup Info PDF

January 31-February 3, 2019 The Superyacht Challenge Antigua Yacht Club

February 16, 2019 Antigua 360º Race

Stan Pearson and a group of enthusiastic sailors involved in Antigua yachting events designed this race as a true and meaningful practice day race before the main RORC event. Inaugurated in 2016, John Burnie’s RP90, La Bete set a monohull race record of 5 Hours 00 Mins 26 Secs for the 52 nautical mile course.

February 19, 2019  The RORC Caribbean 600, Antigua
A 605-mile offshore race around the Caribbean Leeward Islands starting & finishing in Antigua. Organized by the Royal Ocean Racing Club in association with the Antigua Yacht Club.

February 28-March 3, 2019 St Maarten Heineken Regatta

Races and Regattas Calendar
Jambalaya, traditional Carriacou

This world renowned sailing event offers four days of World Class Racing, with trade winds coming from the North East, an average temperature of 25°C and crystal clear waters.

This truly international event had a staggering 37 different countries represented during the Regatta. On shore, participants and spectators will enjoy the culture, cuisine and music from both the Dutch and French side. This regatta is a winning combination; high-energy, competitive racing and unbeatable party fun.

March 9-12, 2019 Loro Piana Caribbean Superyacht Regatta and Rendezvous, BVI 

Spectacular racing will return to the beautiful waters of the British Virgin Islands in March 2018 for the eighth edition of the Loro Piana Caribbean Superyacht Regatta & Rendezvous. Organized by the Yacht Club Costa Smeralda, 2019’s superyacht regatta will welcome an impressive fleet of sailing yachts for three days of thrilling pursuit racing off Virgin Gorda, as well as a sparkling social program.

March 21-24, 2019 St. Barth’s Bucket
This is an invitational regatta open to yachts over 100’. You can buy seats on spectator boats, or charter a yacht to watch these spectacular sailing yachts compete. This three-day invitational regatta features top-notch racing and exclusive shore side social events, all in a breathtaking Caribbean setting.

March 22-24, 2019 St. Thomas International Regatta

BYOB or Charter! Bring you own boat or charter! Chartering especially makes it easy to fly in, jump on a race-ready yacht and set sail! The 47th annual regatta offers three days of unparalleled competition and shore side excitement where sailors can experience reliable breezes, warm azure waters and world-renowned island hospitality.

March 25-31, 2019 BVI Spring Regatta & Sailing Festival 

One of the largest of the races and regattas in the Caribbean, the gorgeous waters around the British Virgin Islands lure over 100 yachts and sailors, friends and families from around the world. Charter a yacht, from spectator to high performance race boats, to participate. Ratings offered are CSA, IRC, HPR and new Multihull.

April 11-15, 2019 Bequia Easter Regatta

A races and regattas favorite in the Grenadines. Sailboats, classic yachts and workboats compete in this event.

April 14-20, 2019 Les Voiles de St. Barth

St. Bartholomew is a top destination for the world’s elite. Whether you’re sailing or spectating, this is one of the most upscale regattas in the Caribbean. Join stunning sailboats that navigate in a festive spirit. Très chic.

Races and Regattas Calendar

April 17-23, 2019 Antigua Classic Yacht Regatta 

Some 50 to 60 yachts compete in these races and regattas. The bulk of the fleet includes a variety of builds; traditional craft from the islands, classic ketches, sloops, schooners and yawls. These yachts together with the stunningly beautiful Spirit of Tradition yachts, J Class yachts and Tall Ships, create an unforgettable event.

April 27-May 3, 2019 Antigua Sailing Week

One of the biggest events in the international sailing calendar, Antigua Sailing Week is one of the most fantastic times to visit Antigua. Whether as a competitor or a spectator, take advantage of an island-wide party. This premier sailing regatta welcomes participants from around the globe competing for the chance to win this prestigious race.

May 8, 2019 Antigua to Bermuda Race

The 2019 Antigua to Bermuda Race is organized by the Royal Bermuda Yacht Club in association with Antigua Sailing Week. The 935 mile offshore race is supported by the Bermuda Tourism Authority and Goslings Rum. The variety of participating yachts includes: hi-tech ocean racers, luxury bluewater yachts and performance cruisers.

May 26-28, 2019 West Indies Sail Regatta, St Barth, FWI

Each year beach built island Schooners & Sloops from all over the Caribbean return to the Port of Gustavia, St. Barths. They commemorate the great days of trading by sail between the islands. Three days of races and regattas are even more exciting with an Island Market, live music and much more…This is a spectacle not to be missed.

Races and Regattas Calendar
Round the Island Race, UK

June 4-8, 2019 Loro Piana Mediterranean Superyacht Regatta Porto Cervo, Sardinia, Italy

This four-day sailing regatta from Yacht Club Costa Smeralda attracts an ever-increasing fleet of renowned sailing yachts.

In 2018 the 130ft sailing yacht ‘My Song’ triumphed as the overall winner. Three-time winner, 148ft sailing yacht SAUDADE, dropped out due to problems with her sails. Anticipation is high to see if SAUDADE will try and reclaim her title at the 2019 event.

A shore-side schedule of events will accompany the racing. Attendees can expect glittering gatherings at exclusive resorts and the YCCS clubhouse.

Charter a sailing yacht or superyacht to join the other yachts following the races. Spectators are warmly welcomed by the event organizers.

May -Jun, 2019  51st Annual Long Island Regatta, Salt Pond, Long Island, Bahamas

The most exhilarating Bahamian sloop sailing action this side of the Caribbean. Pair with all around family fun, live music concerts and taste bud rocking food dishes.

June 18-22, 2019 The Superyacht Cup, Palma, Mallorca

This is the longest running superyacht regatta in Europe. It is a favorite with yacht owners, friends, captains and crew who gather annually for the four day event. Five minutes from the Regatta Village are first class hotels and restaurants. Also, fine shopping, famous architecture, art galleries and historical museums.

June 29, 2019 Round the Island Race, Isle of Wight, UK.

The annual 50 nautical mile course attracts over 12,000 competitors. It is one of the largest yacht races in the world. The ‘Race for All’ ethos embraces first timers, families, amateurs and professionals competing at the highest level. The ‘Race for All’ ethos also supports Official Race Charity, the Ellen MacArthur Cancer Trust, with over £250,000 being raised.

July, 2019 Pacific Cup Race, San Fransisco to Hawaii

“The fun race!” Day after day of incredible downwind sailing, culminating in the thrilling Tradewinds, with steady, firm breezes driving the yachts toward the finish.

Races and Regattas Calendar

July, 2019 Transpac

The 2225-mile LA-Honolulu, bienial Transpac Race, first run in 1906, is known worldwide and makes many bucket lists. Join the elite fraternity of sailors who take on the Pacific Ocean and head west from Long Beach, CA to Hawaii.

August 10-17, 2019 Cowes Week

Cowes, is one of the UK’s longest running and most successful sporting events and is a key highlight of the British sporting summer. Cowes Week is traditionally held during the week beginning on the first Saturday after the last Tuesday in July (except where the tides make the traditional dates virtually unworkable.) Held every year since 1826, except during the two world wars, the race attracts British and foreign royalty and international celebrities.

August 10-18, 2019 Nantucket Race Week

Races and Regattas Calendar

Held on the tiny, isolated island off Cape Cod, Massachusetts, this family-friendly event welcomes participants and spectators alike. The entire Nantucket community comes together for this fun-filled week of regattas, awards ceremonies, and parties. The races provide sport for everyone from young dinghy sailors and families in the household one design to grand prix racers at the very top of their profession. The 47th Opera House Cup Regatta will be August 18, 1019.

August 30- September 2, 2019 Gloucester Schooner Festival

Races and regattas don’t get more family-friendly than the festivities staged in Gloucester’s picturesque harbor. Enjoy Heritage Day, the Boat Parade of Lights, the fireworks display and the spectacular highlight of the Gloucester Schooner Festival, the Parade of Sail, when participating schooners make their way through the harbor and out past the breakwater, to the Mayor’s Race starting area off Eastern Point.

September 28 – October 6, 2019 Les Voiles de St. Tropez, France

Races and Regattas Calendar

This elite event attracts the most modern, extraordinarily high tech, high performance sailing yachts as well as award-winning, legendary classic yachts. World-class race teams and enthusiastic spectators are lured from around the globe to participate in this breathtaking race week.

October, 2019 Columbus Day Regatta, Biscayne Bay, Miami

Join nearly 300 different crews and lots of festivities. The Annual Columbus Day Regatta is the oldest event on Biscayne Bay. The regatta committee is presenting numerous new venues to make this regatta better than ever. Come compete in the race or charter a spectator yacht to watching the regatta or follow the fleet. Races and Regattas off the Miami shoreline offer gorgeous skyline views, balmy waters and super relaxed fun.

Races and Regattas Calendar

October, 2019 Catamarans Cup International Regatta, Athens, Greece

Nothing tops this delightful combination of a sailing race and a relaxing holiday in the Greek islands. Social events include a special welcome for the participants on every island of call, local festivities, prizing awards & ceremonies, cocktail parties, beach BB-Q, dinners and lots of fun. 2018 Catamaran Cup Presentation: CataCup Guide 2018

October 19, 2019 Rolex Middle Sea Race – 50th Anniversary Royal Malta Yacht Club, Malta.

2019 marks the 40th edition of the Rolex Middle Sea Race. The first edition of this epic offshore race took place in 1968, and the Royal Malta Yacht Club is gearing up for what promises to be a very special edition of this highly rated offshore race. The Club welcomes an international mix of professional and corinthian crews in the historic Grand Harbour in Valletta. Over 30 countries were represented in 2018.

November 24, 2019 RORC Transatlantic Race 

The transatlantic race starts in Lanzarote and ends in Grenada. 

November 10 -December 20, 2019 Atlantic Rally for Cruisers (ARC+ and ARC), Las Palmas, Gran Canaria

Of all the races and regattas, the ARC is a ‘must do’ for many sailors, and attracts over 200 boats and 1200 people every year to sail 2700 NM across the Atlantic from Gran Canaria to Saint Lucia.

Some Favorite Charter Racers:

Races and Regattas Calendar

MOJEKA, a beautifully built Moody 54 DS sailing yacht, is ready to take guests on a racing adventure in the Caribbean. Pick your challenge and experience the thrill!!

View MOJEKA description and details

Spectator Yachts:

Regattas and Races Calendar

TREE OF LIFE is a masterpiece of craftsmanship. She combines Old World elegance with modern hull construction, engineering and mechanicals. Experience the adrenaline rush of races and regattas up close with front row seats. TREE OF LIFE! New England charters.


Contact Select Yachts experts to book the perfect charter racing yacht in the destination of your dreams.

ViewRegatta Sailing Yachts 

View: Caribbean Sailing Association Regatta Calendar 2018-2023

View: Caribbean Race Calendar


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