Nevis’ Booby Island Regatta is the Caribbean’s Quirkiest Sailing Event

The island of Nevis isn’t one of the Caribbean’s most distinguished destinations, however its ramshackle beach bars, undeveloped coastline, and lush volcanic peaks are held in high regard by those who have found their way to its verdant shores.

Sitting just two miles east of St Kitts where the newly established super yacht marina Christophe Harbour plays host to the mega yachts of the mega rich, Nevis offers a far more humble and unassuming retreat. Yet it’s in the waters of the straight between these two islands that one of the Caribbean’s quirkiest sailing event takes place.

Each year, over the first weekend in May, Nevis resident and skipper of charter yacht Feisty Miles Denne hosts yachts from all over the world in what I can only describe as a weekend regatta with serious Caribbean flare. Its unique selling point? Anyone can enter, anyone can win.

The quirkiest Caribbean sailing regatta

I think it’s important to point out that the Booby Island Regatta isn’t trying to compete with the likes of Antigua Sailing Week, the BVI Spring Regatta, or St Martin’s Heineken Regatta. Therefore, if you’re a well-oiled team of competitive sorts looking for your next trophy win it’s probably not going to float your boat – pardon the pun.

The Booby Island event is a light-hearted festival that celebrates sailors and skippers of all ages and abilities, as well as craft of all shapes and sizes. Alongside the on-water activity a programme of spectator social events take place on land, so even if you don’t fancy sailing you can still soak up the party atmosphere and explore all Nevis has to offer.

More Nevis travel guides

Planning a trip to Nevis? Check out the other guides in my Nevis travel series.

The Nevis Booby Island Sailing Regatta

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The regatta comprises of either two or three race days depending on the weather forecast and number of entrants however the main events are:

Round de Rock

A round island race that separates the men from the boys, this marathon course sees competitors circumnavigate all 36 square miles (93 km²) of Nevis whilst taking in impressive views of islands Redonda and Montserrat.

The Booby Island Cup race

A classic pursuit race around the now legendary Booby Island which sits in the narrows between St Kitts and Nevis, the final cup race brings the competitors into a close-quarters sprint for victory.

It’s not uncommon for water balloons to canon between vessels and cold Caribs beers to be cracked open on the start line so bring your A-game if you plan to win.

Chase the race by land or sea

If you’re looking for an opportunity to watch the action there are a couple of options to consider:

From a boat

Each year Leeward Island Charters put on a catamaran day-sail, usually on the day of the Booby Island Cup race, for spectators to get up-close to the action. Tickets are sold from the Yacht Club and pick-up is from the pier at Oualie Beach.

From a beach bar

The island’s best beach bars, Yachtsman’s Grill, Chrishi Beach, Turtle Time, and Sunshine’s often host after-parties to celebrate the regatta and make great spots to watch the racing from land (depending on the course).

From Nevis Peak

If the weather is perfect then the best spot on the island to take in the racing is from the top of the peak! You’ll enjoy 360 degree views of the Round De Rock race, although the challenging climb to the top may dissuade you from making the most of the opportunity!

A Booby Island Cup survival guide


Having taken part in my second Booby Island Regatta this year I’ve some useful experiences to share.

If you and your team are planning to race next season, take notes:

  • Polarised sunglasses may assist you in spotting turtles as you sail by. You’ve no chance with regular lenses unless the turtle is bobbing about on the surface.
  • Team shirts are fun, but the Booby Island Regatta T-shirts are bang on trend so pick some up from the Yacht Club when you arrive on the island.
  • Sippy cups are your friend. They’ve saved many a glass of rose from spilling out onto the deck.
  • The handicap system is complex, you will struggle to understand how the prizes are awarded. Just accept you will never fathom the complex algorithmic methods used by the organisers, and move on.
  • Style points are real and water balloons are a potential hazard. Take both very seriously.

Anyone can enter, anyone can win

An anomaly in the Caribbean’s race season, the Booby Island Regatta is ideal for crews looking for a little respite from the fast-paced, and sometimes highly-strung, sailing events elsewhere in the region.

Perfect for families searching for a unique retreat, or friends on the hunt for a memorable escape, the regatta takes entries from everyone and the organisers can even help boat-less crews find a vessel.

Visit, contact Nevis Yacht Charters or the Nevis Yacht Club for more information.


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Planning a sailing vacation? Perhaps I’ll see you on Nevis at next season’s regatta!

Travel Blogger & Photographer
  1. This looks like my kind of island! Love that it isn’t “distinguished”, sometimes that’s just a byword for more formal, more exclusive and more disdainful of those who don’t match the rest of the clientele! Likewise, love that this regatta is similarly open and fun, with anyone allowed to take part. Really enjoyed learning more about Nevis from you, lovely photos too.

  2. Sounds like a really fun event! I love the inclusive nature of anyone can enter and anyone could win – I’ve never had any experience sailing but I would definitely take up the offer of Leeward Island Charters for a catamaran day-sail to get up-close to the action. And then sip at a beach bar to watch the rest of the day!

  3. This looks like such a fun thing to do. Although I don;t sale I would love to go and watch. I spent most of my life living by the sea and I always loved to watch the local Regattas…I think it would be amazing to see one in the Caribbean.

  4. Oh! I’ve never been to a sailing event. Sounds exciting. Polarised sunglasses is a great tip! Will remember to get sippy cups as well. I end up spilling things on a daily basis. So I guess, it’s a must for me.

  5. Oh! Sailing event; I have never seen one till day and never even thought about it. Thanks for telling us about it. The notes you have mentioned are really helpful.

  6. This sailing regatta indeed personifies the spirit of the Caribbean. It sounds so fascinating to chase the race by sea. The chance to spot turtles is an added bonus.

  7. This sounds like my kind of regatta. Love beers at the start line especially an icey cold Carib! Good to hear some yachting not been taken too seriously!

  8. Great article and fun sailing event. These are great helpful hints for those seeking to participate. Nice added bonus of spotting turtles while circling the island. Loads of fun.

  9. This sounds like such a fun experience. I’ve never actually been on a sail boat, so it’s uncharted territory for me! I love that it seems so festive as well AND you got to see sea turtles! How fun is that?!

  10. You make Nevis sound very attract for a laid back vacation. I sat on the beach on Antigua last year looking at that mountain across the water and wondering about it. I am planning a 6-8 week Caribbean island hop tour for next winter (2019). Nevis just moved up the planning priority list.

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