Luxury Caribbean events calendar 2025/2026: The yacht enthusiast’s guide to the best Caribbean festivals, regattas & events

Each year from November to May, the Caribbean becomes the luxury yachting world’s winter playground as the sailing season gets underway and a packed calendar of regattas, social gatherings and VIP soirees keeps guests entertained.

As experts in curating itineraries for discerning yachting guests, Edmiston’s guide to the region’s most refined festivals, events and regattas that complement the Caribbean’s famous carnivals, is the only guide you’ll need.

Luxury Caribbean events calendar (November 2025–May 2026) for yacht charters

From the prestigious St Barths Bucket Regatta to the hotly anticipated Antigua Sailing Week, the Caribbean’s winter sailing events are nothing short of iconic.

However, for a fully immersive Caribbean cultural charter, we can also help steer you towards some of the region’s authentic Caribbean festivals that celebrate its diverse food and cultural offerings for a full-rounded flavour of the isles. Here are the dates to circle in your diary for the season ahead.

NOVEMBER 2025 

St Barth Gourmet Festival – St. Barthélemy, 4-9 November 2025

This annual food and drink extravaganza, now in its 12th edition, is an elegant way of easing into the heady winter social calendar in the Caribbean. 

Bringing together an impressive lineup of world-renowned chefs, many of whom hold Michelin stars, this celebration of the Caribbean’s food offerings is perfect for refined palates.

With tastings complemented by sommelier-selected wines, plus lots of food and drink masterclasses taking place throughout Gustavia Harbour, yacht guests will find themselves at the epicentre of culinary glamour.

Barbados Food & Rum Festival – Barbados, 6-9 November 2025

At this fusion festival where Caribbean fine dining meets heritage rum experiences, the mix of community cookouts, breakfast beach parties and veritable VIP feasts have led to it being named the Caribbean’s Best Culinary Festival for two years running.

A luxury yacht charter to Barbados can anchor near Port St. Charles for an easy transfer to the festival’s more exclusive dinners hosted by some of the region’s top chefs.

Caribbean Rum Awards – St. Barthélemy, 11-17 November 2025

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 and cocktail workshops.

Your luxury yacht charter to St. Barths is the perfect way to get winter celebrations in the Caribbean underway before the busy Christmas period.

Butterfield Bermuda Championship – Bermuda, 13-16 November 2025

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.

The winner will lift the Butterfield Bermuda Championship trophy – a heritage trophy made from Bermuda cedar, the indigenous wood used to build the isle’s early colonial settlements.

Anchor at Hamilton Harbour Marina and take the tender to the course where your VIP hospitality pass will give you access to the prestigious sporting event alongside a select crowd.

Anegada Lobster Festival – BVIs, 28-30 November 2025

The BVIs offer great island-hopping gastronomy events, from Tortola to Virgin Gorda, throughout the year but the Anegada Lobster Festival is undoubtedly the pinnacle of these food showcases.

Kickstart an early December yacht charter with a visit to the ‘Drowned Island’ – the only coral-only atoll in the island group – where you can enjoy exceptional snorkelling, see Anegadian flamingoes up close, and try the spiny lobster for which the isle is famous.

DECEMBER 2025

Mouttet Mile Invitational – Jamaica, 6 December 2025

The Caribbean’s richest horse race, held at Caymanas Park, the Mouttet Mile combines elite thoroughbreds with luxury hospitality, and plenty of Jamaican 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.

JANUARY 2026

Grenada Sailing Week – Grenada, 25-30 January 2026

Since 1993, Grenada has played host to the opening regatta of the Caribbean sailing season – a competitive and intimate regatta held against the most beautiful Caribbean backdrops of Grenada and Carriacou.

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 – The Grenadines, 21 January – 4 February 2026

Welcoming some of the biggest names in the world of blues each year, the Mustique Blues festival, held in the private island’s 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.

Cayman Cookout – Cayman Islands, 14-19 January 2026

A Caribbean yacht charter is not complete without attending a cookout and this well-established event is one of the most sophisticated of all the Caribbean food festivals.

Hosted by Chef Eric Ripert at The Ritz-Carlton, at this culinary gathering you can enjoy some of the island’s best haute cuisine as Michelin-starred chefs, sommeliers, and mixologists, all seek to impress you with their talents.

Anchor off Seven Mile Beach on your Cayman Islands yacht charter for easy tender access to the first-class events and private tastings, with invitations arranged by your crew.

FEBRUARY – MARCH 2026

Sandy Lane Gold Cup – Barbados, 7 March 2026

This storied equestrian event is 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.

St. Barths Bucket Regatta – St. Barthélemy, 12-15 March 2026

The apex of the Caribbean events calendar and undoubtedly its most exclusive regatta, St Barths is the place to be each March to see legendary yachts compete and socialise with the superyacht set. An annual highlight of the Caribbean yacht charter calendar.

Despite being a time-honoured event, the Bucket is not afraid to evolve to meet the needs of modern sailors, and so in 2026, it is adding a fourth day of sailing with a standalone race in response to less reliable trade winds in recent years.

Curacao Invitational Golf Tournament, Curacao, 19-22 March 2026

By invitation only, this coveted pro-am competition pairs 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, BVIs, 23-29 March 2026

A cornerstone of the Caribbean regatta circuit, this early spring event blends competitive racing with sophisticated island soirées 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 2026

Antigua Classic Yacht Regatta – Antigua, 14-20 April 2026

This annual celebration of maritime heritage and craftsmanship is perfect for yachting enthusiasts who appreciate nautical history and style.

Antigua yacht charter guests will be in their element, whether they are enjoying classic yacht racing from the privileged position of their sun deck or getting dressed up for dockside soirées.

Antigua Sailing Week – Antigua, 22-26 April 2026

Hot on the heels of its classic sibling, this five-day event is 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.

Saint Lucia Jazz & Arts Festival – Saint Lucia, 30 April – 10 May 2026

Combining smooth jazz, visual art, and luxury hospitality, this event is rooted in the local community and its soulful melodies are the perfect accompaniment to yacht charters in St Lucia.

Berth at Marigot Bay and attend sunset performances at one of the best Caribbean music festivals for a relaxed island experience.

Embrace the region’s busy events calendar on a luxury Caribbean yacht charter 

The Caribbean’s rich variety of events – held both on and off the water – help set the rhythm for the luxury charter season each year.

Edmiston has some extraordinary yachts well suited to winter Caribbean yacht charters,  including the 96m yacht SOPHIA, an opulent on-the-water sanctuary with some stunning outdoor spaces offering the perfect balance of wellness and fun.

For a more intimate option, try LADY VICTORIA which packs a lot into her sub-50m frame, including a chic rooftop-style sun deck and an extended swim platform for easy sea access.

Speak with an Edmiston broker today and start planning your luxury Caribbean yacht charter today and you could be immersing yourself in this diverse cultural calendar before the season is out.