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Five Reasons to Visit the Caribbean on a Luxury Yacht Charter in Late Spring

By Rebecca Bradbury   Last Updated: 23 May 2023

From local carnivals to international sailing regattas, there are many reasons to visit the Caribbean in late spring on a luxury yacht charter, despite the region’s peak season drawing to a close. With so much to see and do on this beautiful tropical island, read on to discover why you should visit the Caribbean by superyacht during this time.

The Caribbean season runs from mid-December to mid-April, but there are plenty of benefits to undertaking a yacht charter in the region once the crowds have dispersed. Quieter waters will suit those after a more secluded cruising experience, and the days are still warm and sunny, with little rainfall expected.

There is also a fantastic selection of events taking place. Best experienced as part of a private charter vacation, these local gatherings give travelers a rare insight into the unique cultural traditions of the region’s islands. Read on to find out more.  


Although Easter is the busiest time of the month, the long weekend still provides the perfect excuse to swap the unpredictable climes of the northern hemisphere with the guaranteed sunshine and beautiful warm waters of the Caribbean.

As well as relaxing and spending time with loved ones, yacht-goers will also be able to experience the holiday celebrations unique to each island. Jamaica in the Greater Antilles hosts its annual Trelawny Yam Festival, while carnival-style celebrations take place in Virgin Gorda in the British Virgin Islands.

Plus, kite flying is an extremely popular pastime, which peaks on Easter Sunday. After church, islanders in St Lucia, Trinidad & Tobago, and Barbados will unveil their homespun creations to cheering crowds along the sun-kissed beaches and charterers aboard their luxury yachts.

Les Voiles de Saint Barth

Crew sit astride a sailing yacht's port side at Les Voiles de St Barth
A chase boat monitors the race from afar at the Les Voiles de St BarthA foiling race boat trying to keep control at Les Voiles de St Barth

More than 1,000 sailors from all over the world meet each April to partake in a week of competition at the Les Voiles De Saint Barth. From short coastal runs to an around-the-island race, the St Barths regatta challenges even the most experienced competitors.

In addition to the racing, there will also be a lively on-shore social program, culminating on the final evening with a prize-giving ceremony and fireworks display. Be part of the thrilling action on a regatta charter or watch the spectacle from the sidelines.  

St Thomas Carnival

The St Thomas Carnival is a month-long celebration taking place in the yachting hub of the US Virgin Islands. Among the festivities are dazzling pageants, calypso competitions, a traditional games night, water sports activities, steel band jamboree performances and horse races.

Drawing to a close during the last week of April, the carnival concludes with vibrant parades of multi-coloured costumes, dancing troupes and decorated floats. There will also be a fireworks display in Charlotte Amalie Harbour, where superyachts are able to dock.

Antigua Classic Yacht Regatta

In late April, a magical combination of serious racing, laid-back Antiguan hospitality, rum, sunshine and infectious camaraderie bring to life the Antigua Classic Yacht Regatta, which marks the end of the Caribbean’s classic sailing season.

Part of the Panerai Classic Yachts Challenge, the event brings dozens of classic and vintage ketches, sloops, schooners and yawls to the idyllic waters of Antigua for four days of spectacular racing. There is also the unique spirit of traditional class.

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Saint Lucia Jazz and Arts Festival

St Lucia Jazz and Arts Festival
Dancers on stage at the St Lucia Jazz and Arts Festival
A band greets the crowd at the St Lucia Jazz and Arts Festival
A singer warms up at the St Lucia Jazz and Arts Festival

The Saint Lucia Jazz and Arts Festival, running annually in May, has attracted some big names in the past. R. Kelly, Diana Ross and Amy Winehouse have all headlined the event but it’s the dynamic line-up of Caribbean artists that gives the event its unique vibe.

Performances take place across St Lucia, from intimate spots to sweeping venues. Yet, all benefit from the atmospheric island backdrop of lush green mountains and palm-lined beaches. The festival also highlights the island’s local arts scene, with exhibitions, poet performances and local cuisine.

These local events give travellers a rare insight into the unique cultural traditions of each Caribbean island

Thinking of booking a Caribbean yacht charter?

For more details on planning a Caribbean yacht charter, speak to your preferred charter broker

To find out more about chartering in the region, check out our in-depth Caribbean yacht charter guide. For some inspiration, check out our sample itineraries handpicked by experts for the region.

Alternatively, browse all luxury yachts available for charter in the Caribbean.

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