Yacht Charter in the Caribbean

The Caribbean is a paradise destination blessed with a tropical climate, warm and sunny winters and even hotter summers accompanied by steady breezes. Chartering a yacht is opening astonishing doors to the Caribbean region which boasts an astounding 7 000 islands (fewer than 10 % inhabited) divided into two major groups: the Greater Antilles (Cuba, Hispaniola, Jamaica) and the Lesser Antilles (Barbados, Dominica, Grenada).


Sail the Caribbean with its pristine, turquoise waters full of colourful marine life, numerous islands, bays and coves enriched with white sandy beaches and coral reefs. Start your journey from the British Virgin Islands, Martinique, Grenada, Saint Lucia or Saint Vincent and the Grenadines, one of the filming locations of the Pirates of the Caribbean film series to round up a perfect holiday. Besides sailing, there are tons of activities for you, and make sure you explore historical colonial cities such as Havana, Santiago de Cuba and San Juan.

The Caribbean region is best known for its wonderful beaches and pristine waters, but also for its history mostly marked by a long colonial period.
Choose a Boat

Monohull Sailing Boats in the Caribbean

The Caribbean region has perfect sailing conditions for a bareboat charter since it enjoys a year-round warm, tropical climate, while warm, easterly trade winds bring favourable, steady breezes. It is recommended to stay safe during the hurricane season (June-November) and charter a skippered boat; even though direct hits by storm are rare, a seasoned skipper can plan the route for you to avoid the ‘hurricane belt’ areas. Among our Caribbean offers, you can find comfort cruisers which are more affordable, or a bit more pricey performance cruisers - a little something for everyone's taste.

Catamaran Sailing Boats in the Caribbean

Catamaran charter is ideal for the Caribbean region considering that catamarans can easily navigate through shallow waters owing to its low draft, which makes it easy for a bareboat charter. Catamarans are also very capable of manoeuvring around coral reefs for which a skippered charter is recommended if you wish to visit as many destinations as possible, navigating from one island to another and enjoy some sightseeing. The tender on your catamaran’s stern will be an ideal vessel to explore large, turquoise bays where you can drop your anchor and go for a swim or even try snorkelling.

Motor Yachts in the Caribbean

Considering the vastness of the Caribbean region and the sheer number of locations to visit, a motor yacht charter is a perfect tool for such exploration. The performances of motor yachts are more than enough for you to be able to sail the region in no time. Bareboat or skippered, you are guaranteed to have a luxurious experience owing to the great comfort and space a yacht can provide. Simply relax and take your time navigating the islands but also be sure to visit some coastal cities and locations such as Havana (Cuba), San Juan (Puerto Rico), Montego Bay (Jamaica) and Santo Domingo (the Dominican Republic).

Types of Chartering Options in the Caribbean

Bareboat yacht charter in the Caribbean is great for adventurous sailors who like to take control of the helm on the long distance sailing itineraries. You can stick to the islands, so the marinas and bays are always accessible for cover, or you can sail from island to island.

Skippered yacht charter is a great solution where a local skipper’s extensive knowledge will lead you safely to magnificent maritime locations of the Caribbean. Since distances between islands are quite large for a novice sailor, a local skipper will steer the yacht during longer trips, while you sunbathe and enjoy ocean climate.

Crewed charter in the Caribbean will spoil all your senses. A captain is steering the yacht to the hidden private bay, a deckhand is handling all the ropes and systems on the yacht, a hostess is keeping the boat tidy and a cook is preparing delicious Caribbean delights. With such a crew, your mission is to experience an ultimate vacation.

Flotilla sailing holidays - if you want to take your company for a team building or you can’t fit all your friends to one yacht, we have a solution for you. Sail out with two, five or even ten sailing yachts, and share that sailing sensation with all of your friends and colleagues. Imagine ten sailing yachts anchored in a picturesque bay and spending the night there - that is something you have to be a part of.

Why sailing in the Caribbean?

  • You can sail around more than 7 000 islands in the Caribbean Sea
  • The Caribbean Sea has the world’s second largest barrier reef
  • The region enjoys a warm, tropical climate throughout the year
  • Discover great geographical and biological diversity
  • The sailing season starts in December and lasts until May (outside the hurricane season)

Sailing regions in the Caribbean