
The Caribbean holds everlasting wonder in our seafaring imagination, from swashbuckling pirates, smoking communist cigars, to Jack Sparrow and Robinson Crusoe on their tropical adventures. It’s exciting that the only anxiety these islands now bring out in visitors is their abundance of spectacular locations — it’s near impossible to break down which of the near 7,000 islands to visit in your short, yet hard earned vacation.

The British Virgin Islands are often considered the ultimate charter destination, yet somehow this hasn’t affected their unspoilt beauty, nor does it mean you have to fight for sun loungers or share the shade of a palm tree with other holidaymakers. With roughly 50 islands in close proximity to each other, the BVI are one of the most relaxed places to charter a yacht and explore a stunning array of volcanic landscapes, fortress ruins and world class snorkelling – all a stone’s throw away from the five major islands boasting their unique culture, cuisine and boutique shopping. Within the BVI, the best place to charter a yacht is from one of the biggest islands, particularly from Road Town, located on Tortola island, where yachts can be found crewed, or uncrewed in a variety of styles for whatever your seabound adventure requires.

Trinidad and Tobago have an unusual Caribbean feel, Trinidad lies just 11km from the steaming jungles of South America yet remaining distinctly Caribbean at the same time. Tobago is the picture postcard location of the stranded sailor sitting beneath a palm tree on a mound of sand jutting out of aquamarine blue water like a camel’s hump. These can easily be reached by chartering a yacht from Port of Spain, Trinidad, and cruising between the Brocas del Dragon strait, beelining around small reefs and islands towards Tobago, only around eighty kilometres away. Many of the islands have no facilities, so they’re perfect for taking a BBQ and cooler of beer to claim an island to yourself for the day.
With their close proximity to Florida and the US as a whole, the Bahamas are ideal for a quick getaway, maximizing time spent on the open seas, rather than crammed into a plane waiting for landing. The Bahamas boast impressive tourist infrastructure, with over 60% of the national GDP being brought in by holidaymakers. This makes travelling in the Bahamas a breeze. Like many other Caribbean locations, the impressive number of tourists are effectively managed to avoid the impression of overcrowding. This is particularly true of the Bahamas, where over 70% of visitors are part of cruise ships. So chartering a yacht leaves many of the smaller destinations open, as they are too shallow for cruise ships to dock.
While Kingstown, capital of St Vincent and the Grenadines, itself might appear a bit too busy, it’s a perfect place to bring up the anchor and set off for unspoilt beaches. More than just being unspoilt, the Grenadines government is actively taking steps to ensure they remain a paradise for locals and visitors alike. Jet skis, wave runners and spearfishing are not permitted in the Grenadines making them radiate a natural vibe for beachgoers to soak up with some tropical fruit or a BBQ under the stars. Bequia, as the second largest island of the Grenadines is unmissable not only for its laid back atmosphere and brightly coloured buildings, but for the chance to really get to know the locals on this English speaking island.
These are just a few names amongst a seemingly endless list of places that inspire a sense of adventure for a dream holiday. Year-round sunshine, cool breezes and sparkling oceans await whoever takes the first simple steps to decide their destination. The Caribbean is well equipped with English speaking staff in rental companies that have a wealth of experience to tailor a trip to your needs and desires, including bareboat (sail yourself) or luxuriously crewed trips. Many companies also have offices in the US to make organisation all the more simple.