charter flight Caribbean

Caribbean Sailing: Best Locations For An Exotic Experience

Picture the wind in your hair, sun on your skin, sea splashing peacefully, and sails billowing through the tranquil waves. With Caribbean sailing,Caribbean Sailing this dream comes true every day!

This exotic region has several main sailing areas, the most popular including the Grenadines, the US Virgin Islands, and the British Virgin Islands. All three regions have near-perfect Caribbean sailing conditions, with calm waters in the many secluded coves.

Both sets of the Virgin Islands have the most complete sailing structure, however they can also be overcrowded at times – especially the US Virgin Islands. The Grenadines have a less developed sailing infrastructure, but are much less crowded.

Below we discuss the best Caribbean sailing locations and the conditions of each, for you to choose your preferred vacation spot.

Caribbean Sailing

Caribbean Sailing Locations

For the best Caribbean sailing adventure, there are two main locations we recommend most: the Grenadines, and the British Virgin Islands.

If you’re looking for shorter passages over longer water with regularly traveled and well defined routes (and thus more company from other boats), then you’ll most likely love the British Virgin Islands.

On the other hand, if long passages and more privacy (undeveloped bays and secluded beaches) is what you’d prefer, then the Grenadines is your go-to Caribbean sailing spot.

Virgin Gorda Sailing

Caribbean Sailing the British Virgin Islands

The beautiful British Virgin Islands have smooth sailing and short distances between each anchorage – usually less than 3 hours. Even with the large number of sailors, every boat can still find anchorage due to the 20 plus islands (and numerous hidden coves) to choose from.

Often called the Yachting Capital of the World, most yachters and sailors choose these islands, owing strongly to the well-developed boating infrastructure and marinas.

Tortola is the most popular Caribbean sailing island in this region (and also the largest), with hundreds of sailboats available for rent and at least 100 more chartered yachts available. The Moorings is the largest Caribbean provider of yacht charter services in the area.

Also wonderful (but less busy) is Virgin Gorda, where the famous Bitter End Yacht Club offer a wide range of boat rentals and instructors. Less commercialized than the other islands, it is perfect for a private and relaxing sailboat vacation. The island’s North Sound area is a boater’s dream, attracting the best boats to match.

Mustique Sailing

Sailing the Grenadines

Many of the beautiful tiny islands of the Grenadines are impossible to access by commercial airplane, leaving private charters as your premier option. The seclusion of the islands (as well as their unique, vibrant culture) makes them interesting.

Less than 1/3 of the 32 islands and cays of the Grenadines are populated, leaving many untouched and beautiful beaches and bays for you to explore. The waters surrounding the region are warm and calm, but regular trade winds are there to keep your craft moving along.

There is an island for everyone in the Grenadines. Out of the 30 plus islands to visit, Mustique is the most upscale and popular of them all – and our personal recommendation for Caribbean sailing in the Grenadines.

While tiny, beautiful Mustique has several mooring options. It is also popular for having hosted celebrities such as Mick Jagger and Elton John. Nicholson Yacht Charters is one of the most popular local boat charter agents for the Grenadines, and is headquartered in St. Vincent.

Caribbean Sailing Boats

Caribbean Sailing Boats

Sailors who do not have their own boat have two options. One is to rent your own charter boat (called bareboating) – however you will need a sailing course, and some previous sailing experience.

A second, more popular and easier option is to rent a boat with its own skipper. This allows you to learn about (and experience) Caribbean sailing without the stress of running your own boat. The average cost runs between $100-$200 per person per day, not including food and beverages.

Caribbean Sailing Wait<h2 style= Getting There

Caribbean Charter Flights is your premier choice for charter flights to the smaller Caribbean islands. Virgin Gorda and Mustique are both ideal locations for Caribbean sailing, and also two of our featured locations that we are honoured to regularly operate charter flights to.

You can get a quick personalized quote here for your individual trip, or you can leave us your details so we can call you back whenever best. Additionally, please feel free to write us a message with any questions or queries – our Caribbean travel experts will respond promptly.


Image credits: Patrice, Charter World, Maltese, Violetta, Snufkin


VIP Services

VIP Concierge Team

Caribbean Charter Flights offers the following VIP airport transfer services at selected hubs:

  • Personalized Meet & Greet
  • Seamless transfer services between flights
  • Escort through airport terminal with dedicated VIP Service agent
  • Expeditious Immigration & Customs formalities
  • Baggage reclaim & transfer to your next flight

Caribbean Charter Flight