There’s nothing quite like a seaborne adventure. From surfing playful waves to exploring the depths of the ocean floor and all the activities between, the ocean induces nirvana. We, as islanders, are surrounded by another world that is nothing short of incredible. There is no shortage of sailing or yachting experiences in the Caribbean.

Sailing is a popular way to remember that gift. A far cry from the Caribbean’s historical ties to piracy, sailing evolved to offer a fresh take on fun with a touch of luxury. Contrary to persistent belief, it is not only for those with deep pockets.

Best Affordable Yachting Experiences in the Caribbean

These days, there’s no shortage of ways to enjoy life at sea with experiences as varied as the isles of this western archipelago. In multi-island territories like the British Virgin Islands and the Grenadines, sailing is an absolute must if you are to properly appreciate their magnificence. 

For those with the wherewithal, a termed, all-inclusive charter with a crew (which usually runs from 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 across the region offer such services, but the prices vary based on the type, size and age of the boat. Operators such as Dream Yacht Charters and the Moorings, which both service islands like Grenada, Martinique and St. Martin, along with TMM, which is exclusive to the BVIs, are just a few picks from the sizable litter. 

Best Affordable Yachting Experiences in the Caribbean - A luxurious hot tub with ice cold champagne is just one amenity guests can look forward to.
A luxurious hot tub with ice cold champagne is just one amenity guests can look forward to.
Best Affordable Yachting Experiences in the Caribbean
Try out the captain’s hat with a crewless charter.

However, if you’re opting to don the captain’s hat yourself then a crewless charter is the way to go. Whether you choose to wine and dine all alone on the open sea or bring along a few guests for the ride, businesses like Barefoot Yacht Charters, which operates in St. Vincent and the Grenadines, will provide you with the tools and freedom to live out your nautical dreams. Likewise, from Belize to the Bahamas, Sunsail will also more than happily extend the same!

While weeklong stints are the norm for winter travelers, day sails provide a taste of affluence to locals who are either looking for quiet family fun or an epic party in motion. On islands like Jamaica and Trinidad, sailing soirees abound. Liquor flows like the currents of the Caribbean Sea and good vibes “cyah dun.”

In contrast, romantic sunset tours and snorkel trips, both private and shared, are also available for those who would rather take to the seas in a more low-key fashion. Though shorter, these trips still offer luxury and exclusivity. Amenities might include a gourmet meal and rum punch on tap. For an additional cost, extra water toys like jet skis, paddleboards and kayaks can be added to enhance the experience. Barbados-based Seaduced Charters has taken luxury day sailing to new heights by even including a private chef and a premium bar.

Best Affordable Yachting Experiences in the Caribbean

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

  1. Sail during the off-season: Some companies will offer cheaper rates during down times to keep business going, so plan your travel calendar to your advantage.
  2. Ask for the “locals discount:” During the height of the pandemic, charter companies like Anne Bonny in the BVI used this strategy to stay afloat. It’s now a permanent fixture in their operations and is a hit with residents of the territory.
  3. Maximize the boat’s capacity: Determine the boat’s passenger capacity beforehand and split the bill by bringing your friends and family. Shared tours scheduled by the charter company also result in these savings. Not only is this a surefire way to keep costs low, it’s a great way to create an unforgettable experience.
  4. Join a yacht club: This is the ultimate social club for seafarers! 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 an opportunity for inter-island hopping may even come your way.

Bitten by the sailing bug? 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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