These are the best yachting experiences in the Caribbean


There’s nothing quite like a maritime adventure. From surfing playful waves to exploring the depths of the ocean floor and everything in between, the ocean induces nirvana. As islanders we are surrounded by another world which is simply amazing. There is no shortage of sailing or yachting experiences in the Caribbean.

Sailing is a popular way to remember this gift. Far from the Caribbean historical links with piracy, sailing has evolved to offer a new approach to pleasure with a touch of luxury. Contrary to persistent belief, it’s not just for those with deep pockets.

Best Affordable Caribbean Yachting Experiences

There is no shortage of ways to enjoy life at sea these days with experiences as varied as the islands of this western archipelago. In multi-island territories like the British Virgin Islands and the Grenadines, sailing is an absolute must if you want to fully appreciate their magnificence.

For those who can afford it, an all-inclusive crewed charter (typically lasting five to 10 days) is guaranteed to make you feel like the star in an episode of “Lifestyles of the Rich and Famous.” A plethora of companies scattered around the area offer such services, but prices vary depending on the type, size and age of the boat. operators such as Dream Yacht Charter and the Mooringsof which the two service islands like Grenada, Martinique and Saint-Martin, as well as TMM, which is exclusive to the BVI, are just a few choices among the significant reach.

Best Affordable Caribbean Yachting Experiences - A luxurious hot tub with chilled champagne is just one of the amenities guests can look forward to.
A luxurious whirlpool tub with chilled champagne is just one of the amenities guests can expect.
Best Affordable Caribbean Yachting Experiences
Try the captain’s hat with a bareboat charter.

However, if you choose to wear the captain’s hat yourself, a bareboat charter is the way to go. Whether you choose to wine and dine alone on the open sea or take a few guests along for the ride, businesses like Barefoot Yacht Charter, which operates in St. Vincent and the Grenadines, will provide you with the tools and freedom to live your nautical dreams. Similarly, from Belize to the Bahamas, Sun sail will also more than happily extend the same!

While week-long stays are the norm for winter travellers, day sails offer a taste of the crowds for locals looking for either quiet family fun or an epic party on the move. . On islands like Jamaica and Trinidad, sailing parties abound. The alcohol flows like the currents of the Caribbean Sea and the good “cyah dun” vibes.

On the other hand, romantic sunset excursions and snorkeling trips, both private and shared, are also available for those who prefer to take to the sea in a more discreet way. Although shorter, these trips still offer luxury and exclusivity. Amenities can include a gourmet meal and a rum punch on tap. For an additional cost, additional water toys like jet skis, paddle boards, and kayaks can be added to enhance the experience. Based in Barbados Seaduced Charters took luxury day sailing to new heights by even including a private chef and upscale bar.

Best Affordable Caribbean Yachting Experiences

Not just the adventure of daydreaming, sailing can be within your reach with the following tips:

  1. Sail out of season: some companies offer cheaper fares during off-peak times to keep business going, so plan your travel schedule to your advantage.
  2. Ask for the “locals discount”: At the height of the pandemic, charter companies like Anne Bonny at the BVI used this strategy to stay afloat. It is now a permanent fixture of their operations and a hit with residents of the territory.
  3. Maximize Boat Capacity: Determine the boat’s passenger capacity in advance and split the bill by bringing friends and family. Shared tours scheduled by the charter company also result in these savings. Not only is it a surefire way to cut costs, but it’s also a great way to create an unforgettable experience.
  4. Join a yacht club: This is the ultimate social club for sailors! Here you will always find someone looking for a plus one, or five, to accompany them on a leisurely sail. And if you’re lucky, maybe the opportunity to go from one island to another will come your way.

Bitten by the sailing virus? Check out some of these sailing events across the West Indies in 2023:

  • Barbados Sailing Week: January 18-23
  • St. Maarten Heineken Regatta: March 2-5
  • St. Barths Bucket Regatta: March 15-19
  • BVI Spring Regatta & Sailing Festival: March 27 to April 2
  • Bequia Easter Regatta: April 6-11
  • Antigua Sailing Week: April 29 to May 5


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