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Sailing St. Martin: The Best Festivals to Visit by Yacht

Bareboat Caribbean Events

Sailing from St. Martin is one of the best ways to explore a stunning and diverse part of the Leeward Islands of the northeastern Caribbean, defined by its eclectic culture, idyllic beaches and culinary delights like no other. As well as the year-round sailing, beaches and tropical delights on offer, this beautiful part of the world is also famous for its festivals, sailing events and celebrations.

If you’re searching for the best festivals to visit by yacht in the Caribbean, we’ve got your back. Our team of experts has collated a list of some of the must-see events, ideal for adding to your St. Martin sailing itinerary!

The Best Festivals to Visit by Yacht from St. Martin

festival in st. martin sailing

Festivals of St. Martin

St. Martin is one of the most popular destinations in the Caribbean for sailing, and it’s easy to see why. Situated around 150 miles north of Guadeloupe, the picturesque island offers a combination of French and Dutch culture and cuisine. Explore world-class restaurants, casual coastal bars, legendary beaches and more – all within walking distance of your very own super yacht.

If it’s the festivals of St. Martin you’re interested in, sailing is one of the best ways to see everything on your wishlist. Set sail from Dream Yacht’s St. Martin base to reach nearby islands and discover their incredible calendar of events…

  • Grand-Case “Fat Tuesday” – Street fair offering food, arts and music, hosted weekly from January through to April.
  • French Side Carnival – Two weeks of colorful parades featuring zouk and reggae music on the streets of Marigot and Grand-Case, hosted throughout February.
  • Heineken Regatta – Largest sailing event in the Caribbean for unmatched spectator entertainment, hosted 29th Feb – 3rd March 2024.
  • SXM Festival – Week-long electronic music festival in St. Martin, hosted 11th – 18th March 2024.
  • Flavors of St Maarten Food & Wine Festival – Showcase of the Island’s best chefs and their signature dishes, hosted throughout November. Locations vary year to year, but the boardwalk in Philipsburg always has plenty of events on offer – perfect for sailing vacations.
festival in st. martin marina

Festivals of St. Barts

If you’re looking for an exclusive island getaway, St. Barts is the ultimate destination. Only accessible by boat or a small plane, it’s the perfect option for a sailing vacation in the Caribbean. Explore coast-to-coast in under 30 minutes and mingle with the world’s A-listers, all while taking in the vibrancy and uniqueness of Caribbean culture.

If it’s the festivals of St. Barts you’re looking for, you’ve come to the right place. While chartering with Dream Yacht, you can experience some of the best festivals to visit by yacht in the Caribbean, including the most revered sailing events, celebrations and more…

  • St. Barth Music Festival – Featuring world-class musicians, symphony orchestras and more, hosted 15th-21st January in Gustavia.
  • Carnival (Mardi Gras) – Beginning the first Sunday every January after Epiphany, this awe-inspiring celebration features street parades, music, dancing and more through the streets of Gustavia. Hosted every Sunday afternoon until Mardi Gras.
  • St. Barths Bucket Regatta – Perfect for thrill-seekers, this famous sailing event is a must-see for yacht vacationers, featuring a variety of races and entertainment. Hosted 21st-24th March 2024.
  • Bastille Day (French National Holiday) – Enjoy fireworks, dancing and cultural celebrations on the Quai Général de Gaulle, Gustavia. Hosted 14th July annually.
  • St. Barth Gourmet Festival – Hosted annually in November, this food-focused festival celebrates island cuisine like you’ve never seen it before.
  • St. Barth / Gustavia Christmas Village on the Docks – Explore an adorable Christmas market on the quays of the port of Gustavia, hosted early December each year.
culinary festival anguilla

Festivals of Anguilla

Small but mighty, Anguilla is an island situated in the Caribbean, just a few miles north of St. Martin. Accessible by boat from your Dream Yacht base at St. Martin, it’s an idyllic spot to explore – free from the usual tourist crowds.

Known as the culinary capital of the Caribbean, exploring the island’s food scene is a must, as well as the festivals of Anguilla that run all year round. Add our selection of the best festivals to visit by yacht to your sailing vacation itinerary – you won’t regret it…

  • Anguilla Summer Festival – Hosted throughout July and August, this summer-themed celebration offers a Caribbean carnival-style event, including music, dancing, street parades and beach parties. The festival commemorates the emancipation from slavery in the British Caribbean.
  • Sandy-Ground Festival – Held on Assumption Day (15th August 2024), this exciting festival in Anguilla celebrates the thrill of traditional games, music and cuisine.
  • Anguilla Culinary Experience – Four days of curated culinary experiences between 23rd-26th May 2024. The festival raises funds to support culinary education for the island’s next generation.
st. barts sailing festivals

Ready to Charter a Yacht in the Caribbean?

At Dream Yacht Charter, we’re the experts when it comes to sailing holidays – whether you’re looking to enjoy bareboat catamaran sailing in St. Martin or discover the ease and social fun of a St. Barths Dream Premium cabin cruise.

Make sure you see the best festivals to visit by yacht in the Caribbean, plus all of the sights and experiences your vacation party will never forget. Explore St. Martin sailing holidays today on our website and book your next adventure.

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