Luxury Caribbean events 2026/2027: The best festivals, regattas & events

As the world’s winter playground for yachting, the Caribbean is the epicentre of the global luxury events scene each year from October to May. Edmiston brings an expert understanding of both superyacht travel and the cultural calendar, creating itineraries that place you at the heart of the season’s most important events.

Here, we highlight some of the best Caribbean festivals, events and regattas to build into your itinerary this season, from Caribbean food festivals and music festivals to the yachting calendar’s leading Caribbean regattas, bringing together the best of Caribbean life both on and off the water, and beyond the carnival. This calendar of events in the Caribbean is built for the luxury yacht charter season, spotlighting the moments most worth sailing for.

Luxury Caribbean events calendar 2026/2027

October 2026 Caribbean events

BVI Restaurant Week – Tortola, BVI, 20-24 October 2026

An annual culinary event highlighting some of the best restaurants in the BVIs, with special offerings from top island chefs – BVI Restaurant Week is ideal for guests wanting a low-key gastronomic prelude to the BVI’s high season. Anchor off Tortola’s West End to enjoy BVI Restaurant Week and discover the full range of luxury things to do in BVI before the crowds arrive.

Butterfield Bermuda Championship – Bermuda, 22-25 October 2026

This PGA-sanctioned golf tournament draws elite players to the immaculate greens of Port Royal Golf Course, with play taking place against a backdrop of sweeping Atlantic vistas. Anchor at Hamilton Harbour Marina and enjoy VIP hospitality passes with seamless tender transfers to the course.

Jounen Kwéyòl (Creole Heritage Day) – Dominica & Saint Lucia, 25 October 2026

This celebration of Creole culture has been held on the last Sunday in October since 1981 and highlights the significance of the Kwéyòl (Creole) language to local identity. A great option for early arrivals to the region, anchoring between Saint Lucia and Dominica, looking to get their vacation off to an authentic start.

Caribbean Rum Awards – St. Barths, 26-30 October 2026

This boutique event, held at the five-star Christopher Hotel in St Barths, celebrates the rich variety of rums available throughout the islands, through blind tastings, cocktail workshops, and rum and cigar pairings. A great excuse for a St. Barths’ stopover ahead of the December Caribbean charter season.

November 2026 Caribbean events

Barbados Food & Rum Festival – Barbados, 5-8 November 2026

At this fusion festival where Caribbean fine dining meets heritage rum experiences, the mix of community cookouts, breakfast beach parties and VIP feasts have led the Barbados Food & Rum Festival to be twice named the Caribbean’s Best Culinary Festival.

This year the event coincides with Barbados’s 60th anniversary of independence and guests on luxury yacht charters in Barbados can anchor near Port St. Charles for easy transfers to shoreside VIP dinners, hosted by some of the region’s top chefs.

Grenada Flower & Garden Festival  – Grenada, 8-15 November 2026

This year sees this inaugural show celebrating Grenada’s natural beauty and rich floriculture. Yacht guests can dock in Port Louis, with options to explore the island’s lush flower gardens or take a waterfall hike to Mount Carmel or Seven Sisters Waterfalls.

St Barth Gourmet Festival – St. Barths, 9-15 November 2026

Returning for its 13th edition, the St Barth Gourmet Festival is the premier gastronomy event in the Caribbean and a delicious way to ease yourself into the Caribbean’s winter social season.

Attracting an impressive lineup of world-renowned chefs – many of whom hold Michelin stars – and sommeliers, and with Gustavia Harbour at the heart of festivities, yacht guests will find themselves in the culinary centre of it all.

Anegada Lobster Festival and British Virgin Islands Food Fete – BVI, 27-29 November 2026

The BVIs offer great island-hopping gastronomy events, from Tortola to Virgin Gorda, as part of the BVI Food Fete, culminating in the famous Anegada Lobster Festival. Here, as well as sampling the spiny lobster for which the isle is famous, guests can enjoy exceptional snorkelling and see Anegadian flamingoes up close. The perfect culinary itinerary for a late November/early December yacht charter.

December 2026 Caribbean events

Mouttet Mile Invitational – Jamaica, 5 December 2026

Held at Caymanas Park, in Jamaica, the Mouttet Mile is the Caribbean’s richest horse race, combining elite thoroughbreds with luxury hospitality, and plenty of cultural flair. Anchor at Port Royal Marina and fly in by private transfer for race day for an unforgettable outing on your southern Jamaica stopover.

Christmas in the Grenadines — Seclusion at its Most Spectacular

For those who value privacy over the social spectacle of St. Barths, the Grenadines offers one of the Caribbean’s most beautiful Christmas yacht charter experiences, where you will have the region’s turquoise waters largely to yourself. 

Starting at St. Vincent, your Grenadines yacht charter can travel through Bequia, Mustique, Canouan, and the Tobago Cays, with no fixed schedule, offering complete flexibility, with your crew able to arrange private Christmas dinners on board or ashore.

Boxing Day Junkanoo – Nassau, Bahamas, 26 December 2026

One of the Caribbean’s most visually spectacular cultural events, the Boxing Day Junkanoo parade through Nassau’s Bay Street is easily one of the best post-Christmas celebrations.

The parade begins in the early hours of Boxing Day morning, so anchor in Nassau Harbour on Christmas night and tender ashore before dawn for the best position and you can be back on board in time to see the sun rise over the harbour.

New Year’s Eve in St. Barths – The Caribbean’s Most Coveted Night, 31st December 2026

Though the whole festive period in St Barths can be seen as one continuous social event, it reaches its peak on New Year’s Eve, making it one of the most important dates in the Caribbean superyacht calendar.

As Gustavia is filled with some of the most incredible yachts in the world and beach clubs and restaurants host invitation-only celebrations, you’ll want to be back on deck by midnight to witness the fireworks spectacle over the harbour.

Prime berths are booked 12-18 months in advance so it’s essential you speak to your Edmiston broker as soon as possible if you’re hoping to attend.

Colombier Bay is a good alternative to Gustavia as a tranquil anchorage with tender access to celebrations, for guests who prefer privacy with proximity.

January 2027 Caribbean events

Barbados Sailing Week – Barbados, 15-21 January 2027

A rising fixture on the regatta calendar, this event combines competitive racing with Barbados’s renowned hospitality. Pair attendance here with the Barbados Gold Cup for a full Barbados social season itinerary.

Grenada Sailing Week – Grenada, 31 January – 5 February 2027

The opening regatta of the Caribbean sailing season, Grenada is a competitive and intimate regatta held against some beautiful Caribbean backdrops. Race days depart from Port Louis Marina, making it an ideal stopover for Grenada yacht charter guests hoping to join the circuit.

Mustique Blues Festival 2027 – The Grenadines, 2027

Welcoming some of the biggest names in the world of blues each year, the Mustique Blues Festival, held in the island’s iconic Basil’s Bar, is an intimate seaside event that unites world-class musicians with a laid-back island attitude.

Anchor off the isle of Bequia, or Mustique itself, on your yacht charter in the Grenadines for a wonderful, mid-season cultural interlude.

March 2027 Caribbean events

St. Barths Bucket Regatta – St. Barths, 17-21 March 2027

The apex of the Caribbean events calendar and undoubtedly its most exclusive regatta, St Barths is an annual highlight of the superyacht social scene.

Despite being a time-honoured event, The Bucket Regatta is not afraid to evolve to meet the needs of modern sailors, and so in 2026, it added to its Caribbean regatta schedule, with a fourth day of sailing with a standalone race in response to less reliable trade winds in the preceding years.

Sandy Lane Gold Cup – Barbados, 2027

The Sandy Lane Gold Cup is a storied equestrian event and a high point of the Barbados social season, attracting royalty, celebrities, and discerning jet-setters trackside each year.

Berth at Port St. Charles Marina on your Barbados yacht charter and you can combine a day at the races with a private coastal charter around the island, dropping anchor by some of the famously beautiful beaches as the mood takes you on your luxury Caribbean yacht charter.

Curacao Invitational Golf Tournament – Curacao, 2027

By invitation only, the Curacao Invitational Golf Tournament is a coveted pro-am competition, pairing tropical elegance with championship-level play at the luxurious Blue Bay Golf & Beach Resort.

Anchor your Curacao yacht charter near Willemstad and combine tee-off mornings with relaxed cruising around the island’s many hidden coves.

BVI Spring Regatta & Sailing Festival – British Virgin Islands, 29 March–4 April 2027 

A cornerstone of the Caribbean regatta circuit, the BVI Spring Regatta blends competitive racing with sophisticated island gatherings across the isles of Tortola, Virgin Gorda, and Jost Van Dyke.

Whether you wish to spectate or participate, BVI yacht charter guests can make good use of the exclusive berths available at Nanny Cay and Scrub Island.

April – May 2027 Caribbean events

Antigua Classic Yacht Regatta – Antigua, 14-19 April 2027

Hot on the heels of its classic sibling, Antigua Sailing Week is a five-day event and the crowning glory of Caribbean regattas and a thrilling close to the sailing season. Antigua yacht charter guests can combine their love for competitive sailing with the island’s glamorous nightlife and social scene.

Antigua Sailing Week – Antigua, 21-25 April 2027

Hot on the heels of its classic sibling, Antigua Sailing Week is a five-day event and the crowning glory of Caribbean regattas and a thrilling close to the sailing season.

Antigua yacht charter guests can combine their love for competitive sailing with the island’s glamorous nightlife and social scene.

Grenada Chocolate Festival – Grenada, 22-29 May 2027

A luxury foodie experience blending island sustainability, farm-to-bar dining, and tropical indulgence, this is a Caribbean festival you’ll want to arrive hungry for. Dock at Port Louis Marina and join a private plantation tour, arranged by Edmiston.

Aruba Hi-Winds – Aruba, 2027

For yacht guests who like some thrills with their turquoise views, Aruba Hi-Winds is the Caribbean’s premier windsurfing and kiteboarding event – a week of high-octane sport, oceanfront parties, and spectacular coastal scenery.

Anchor off Palm Beach for a front-row seat to the competition, while calmer coves nearby are perfect for guests who prefer to spectate from the water.

Saint Lucia Jazz & Arts Festival – Saint Lucia, 30 April – 9 May 2027

Combining smooth jazz, visual art, and luxury hospitality, the Saint Lucia Jazz & Arts Festival is rooted in the local community.

Berth at Marigot Bay and attend sunset performances at one of the best festivals in the Caribbean 2027 for a relaxed island experience on your St Lucia yacht charter.

Plan your Caribbean yacht charter around the season’s finest events

Together these events define the rhythm of the Caribbean’s luxury charter season from October through May. Beyond the events you can explore the Caribbean yacht charter regions that most inspire you, whether you love indulging in the best spas in the Caribbean, seeking out the top dining options in the Caribbean, a day of Caribbean hiking inland, or dropping anchor off remote Caribbean islands far from the crowds. However your season unfolds, Edmiston is on hand to help you shape it.

Speak with an Edmiston broker today to design a bespoke Caribbean winter yacht charter that takes in the events you wish to attend this season.