Island hopping by boat is one of the joys of the Caribbean. Sailing, with all its sense of freedom, enables you to see a variety of islands at your own pace, enjoying the tropical wind and seas and exploring coves and beaches that cruise ships and landlubbers cannot reach. The islands, often within sight of one another, look wonderful as you approach them, rising from the horizon until they tower above you. Then you disembark onto a rickety wooden jetty among the palms or pull into an isolated cove and swim ashore.

If you wish to charter a yacht in the Caribbean you must decide whether you are experienced enough and want to take command of your own bareboat (in which you look after yourself) or if you would prefer to be looked after on a crewed yacht - and whether it should be a sailing or a motor yacht .

See full details through the options below . Next you must decide whether you would prefer to arrange your trip independently by working through a yacht charter company or the owner direct, or whether you would prefer to book your holiday through a travel organiser.

Bareboats | Skippered Yachts | Motor Yachts | Crewed Charter
Stay-Sail | Sailing Cruises

Any of these types of sailing holidays can be combined with a stay on land. Some hotels and a few villas have their own yachts for stay-sail holidays.

Cruising the Caribbean offers similar variety. On DefinitiveCaribbean we have a selection of small cruise ships that provide personal service and an intimate experience. Some are extremely sleek, with stylish, sumptuous cabins, but there also barefoot cruises on tall-ships with a full rig of masts and sails.

For our advice and selection of the BEST CHARTER COMPANIES, YACHTS, STAY SAILS & CRUISES serving each island, please select by island below: