Puerto Rico’s regattas: an endless celebration of sailing

The mass of floating vessels, their colorful sails stretched tight by the breeze and glinting in sunlight, is a sight to behold…

By Peter Martin
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With shimmering emerald and deep blue waters beckoning off its hundreds of miles of shoreline, Puerto Rico is a sailing paradise. You’ll feel the lure of the sea from San Juan to Dorado to Isabela, along the north coast; Guanica to Mayaguez to Aguadilla in the southwest; and Humacao to Salinas to Ponce along the southeast.

The east coast of Puerto Rico is the start of the world’s most pleasurable sailing area, a swath of virgin sea, dotted with coral and green islands. Fajardo splits the waters of the Atlantic Ocean and the Caribbean Sea at Puerto Rico’s northeast corner, ringed by marinas and miles of undeveloped coast.  And it is just one of part of the sailor’s heaven that is Puerto Rico.


The waters off Puerto Rico are excellent for sailing and other boating throughout the year, with winds averaging 10 to 15 knots, plush full service marinas with state-of-the-art facilities that are the envy of the Caribbean and plenty of offer, whether you are looking to charter a fully crewed sailboat, or want to spend the afternoon snorkeling from a catamaran, or rent a small sunfish for the afternoon.

If sailing is your thing, you can do it all in Puerto Rico. There are numerous sailing schools, chartering of world-class vessels, and day sailing and fishing trips operating out of most island marinas, which are plentiful. San Juan has three full-size marinas, while Fajardo has seven. The coast is literally ringed by them, with at least one existing in any town with access to the coast, and in large vacation areas, often several. 

To get your first taste of sailing, consider a snorkeling trip off the coast of Fajardo on a giant luxury catamaran, or perhaps a sunset cruise off San Jan Bay or the coast of Rincon. The catamarans are outfitted with bars and great sound systems, and lunch is usually served on a beautiful beach of a sun struck cay in the midst of the sparkling Caribbean, and the snorkeling is even more amazing, an easy window into the tropical undersea world that takes your breath away. The nighttime trips are more laid back but just as refreshing, especially with the wine and hors d’oeuvres that are often served.

Expert sailors can rent their own, whether it’s a small sunfish or a full-sized yacht charter. There are also smaller water sports outfits that rent windsurfer and kite surfer equipment, as well as standup paddleboards.

Puerto Rico is also the perfect starting point for your dream vacation, a private yacht sailing charter through the waters of tropical paradise. Big game fishers, meanwhile, have some impressive fishing vessels to charter from the east coast to the west. San Juan is actually one of the best deep sea fishing destinations, with big game fishing grounds just minutes north of the city coast toward the great abyss of the Puerto Rico Trench, and several impressive fishing vessels for rent that also sport plus interiors, and other perks like gourmet food and drinks.

Regardless of where you are in your sailing journey, your experience here will likely be a fulfilling one. Experience a regatta, if you really want to submerge into the world of sailing, where serious sailors compete offshore, while spectators swim through a series of pleasures. Regattas are a day long fiesta that stretches across the night, often with live music, culinary diversity, and sociable bar areas, and other fun, games and prizes. They are also serious competitions that make for fascinating spectator sport. 

Puerto Rico is home to several important regattas, one reason it is really one of the sailing epicenters of the world, and not just the Caribbean. However, another big reason to experience a regatta here is that it will reflect Puerto Rico’s prowess as a party power, with every regatta as concerned for the entertainment experience it provides visitors as it is for the competitive environment it providers its sailors.

The island’s biggest is probably the Puerto Rico Heineken International Regatta, which launches in the month of May from Palmas del Mar in the middle of Puerto Rico’s east coast. The event is held at the close of the Caribbean sailing season but the start of summer, and has slowly become an annual rite of passage on the island over its decade long existence.

Sailors from across the Caribbean and other oceans come every year to compete at the event, one of the most prestigious in the region that attracts all types of vessels.  The event hosts Hobie Cats, Optimist, Sunfish, Laser, Native boats and Chalanas. Other classes are CSA Racing, PHRF Jib &Main, Melges, Raya, Mariner, and Hunter. There is also a Puerto Rico International Dinghy Regatta at the same time, where small boats race in the harbor. Prizes totaling $12,000 are paid out across the categories. The event is part of a new sailing circuit, the Heineken Star Cup, which unites the Heineken sponsored events across the Caribbean.

The fiesta continues at night, with live music, food, other festivities, and so much more.

The International Bay Regatta Bahia Urbana in February turns San Juan Bay into one of the world’s most vibrant sailing celebrations, combining world-class competition by day and nightly entertainment, including top of the line musical performances. You can take it all in from the bayside park that bears the regatta’s name. It’s the perfect spot to sip a cool tropical drink while watching the colorful sails darting across the bay, and  big screen video screens bring the action up close. You also have a front row seat for the nocturnal entertainment extravaganza. Sailors from Puerto Rico and around the world participate, as do popular Latin pop, electronica, and DJ and tropical music acts. And it’s all free and open to the public.

The Club Nautico of San Juan is the regatta’s host club and opens its facilities to vessels and sailing crew. The Regatta specializes in match racing – a series of short races between two vessels, run near the coast for the public to see.

The Club Nautico de San Juan International Regatta sails out of the city’s finest marina, at a stretch of waterway brushing against Condado, Miramar, and Puerta de Tierra, during the month of December.

Held every winter during high season, the event is an outgrowth of the Club’s junior sailing program, which dates back to the 1970s, so features youthful competitors. Headed into its 15th year, the event offers Caribbean Sailing Association-sanctioned workshops and like any island fiesta, plenty of food, drinks, and entertainment.

In 2015, there were 20-plus-knot wind gusts, roiling the sea and creating fresh challenges for the competitors from across the Caribbean. The regatta hosts both small boats and larger sailing vessels across categories.

Puerto Del Rey marina in Fajardo hosts the three-day Puerto Del Rey Sailing Challenge, another top rate event scheduled in March, which draws 100 vessels from across the region.

There is tough and skilled competition in every category, but the engaging event is a laidback affair and a good spot for newcomers to competitive sailing.

The event has nightly live music concerts, which have drawn the top pop acts in Puerto Rico, and an all-day kids festival. There’s something cooking at any hour, including wonderful food at various different spots at this gorgeous marina. This is the gateway to the Eastern Caribbean sailing paradise.

The Culebra Cup is an annual summer regatta held in July that perfectly captures the free-wheeling spirit of sailing.

Sunday may be the race day, which takes place in the picture-perfect Caribbean waters off the coast of the gorgeous island town of Culebra, but festivities get started back on Puerto Rico’s East Coast with a Friday night happy hour at Fajardo’s Villa Marina Yacht Harbour.

After the party, competitors and other sailors then meet early Saturday morning on the small island of Palominos, your typical tropical isle paradise, and then take off for a sail rally across a gorgeous stretch of reef-choked sea to Culebra. The mass of floating vessels, their colorful sails stretched tight by the breeze and glinting in sunlight, is a sight to behold; they soar across the water’s surface as if a single being, like a formation of giant winged migratory birds heading into the west.

Saturday night is a big party with live music, food and drinks in Culebra’s town plaza, where a great time is had by the entire island, and the visitors from around the world get to enjoy this enchanted land of sea.

The day-long Culebra Cup, which circuits much of the island, is a sailor’s delight, an amazing water course that challenges competitors, who must run west while tacking east throughout the event. The awards ceremony that evening is another celebration, and the experience closes the following Monday with a sailboat rally back to Fajardo.

The event is organized by the good-natured Borinquen Islands Sailing Association, known as BRISA, or breeze in Spanish. The non-profit consists of a group of sailing enthusiasts who seek to engender their passion for their sport in others through regattas and fishing competitions, as well as educational and social activities.

The Discover the Caribbean Regatta at the Ponce Yacht and Fishing Club on the south coast is one of the island’s oldest sailing competitions, and this year it will be celebrating its 27th edition.

The regatta, held in late October and November, attracts sailors from across Puerto Rico and Caribbean, with three full days of competition and plenty of activities on shore. It’s continuing popularity and staying power stems from its reliance on the tried but true formula of offering participants the generous hospitality Puerto Rico, fantastic racing conditions, and lots of partying and family fun, like a park of inflatable attractions for the kids.

The event comprises different competitions there are Halloween costume parties, dinghy and stand up paddle board competitions, as well as explorations of the offshore Coffin Island and other natural wonders. There’s also serious sailing amidst the fun.

If fantastic racing, great family fun, plenty of parties, and beautiful blue seas sound like your idea of a good time, make sure you don’t miss out in experiencing on one of Puerto Rico’s thrilling regattas.

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