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Planning a Caribbean Sailing Trip

Now that you have finally decided to take some time off work and soak your senses in the luxury of travelling on a Caribbean sailing charter to take you to your dream destinations, it time to start planning your trip.

Crewed Charter or a Bareboat

Depending on your budget and other preferences, the first thing to decide is whether you want a crewed charter yacht or a bareboat charter. If you want to enjoy the convenience of a cook, a captain, a skipper, and engineers to assist you during your trip, you might prefer going for a crewed sailboat charter. However, if you are a trained sailor yourself and can take care of your guests on board, hiring a bareboat might be a better idea.

 Weather

The dry season in the Caribbean is from February through June. From July onwards, frequent showers begin with lots of sunshine. Sometimes there are intense rains and strong winds blowing through the season, but it’s safe to take a Caribbean sailing charters into the sea during this time. However, in winters from November to February, the sea can produce strong winds that make it unsafe for anchorage. While booking a sailboat charter in the off season can cost you less, it’s important to make sure that you have not planned a trip during hurricane season.

Catamaran versus Monohull

A catamaran is a multihull as opposed to a monohull sailboat charter. Catamarans offer luxury of space, stability, privacy, comfort and have a large cockpit as well. Some can be so luxurious that they offer all the facilities one can avail in a five star hotel. This is the perfect vessel for those who want to enjoy and relax during their sailing trip. A monohull, on the other hand, is for those who are more interested in exploring the art of sailing. Such sailboat charters get wet easily and offer somewhat less comfort than a catamaran; nonetheless, their sailing performance is far better than catamarans.

Planning the Trip

Selecting crew members, the base port to begin your trip, the islands you want to visit in a given time frame and the activities you want to perform are things to consider before departing.

Getting Cleared

Customs and immigration are important aspects of getting across the borders with ease. The Windward Islands cover four separate countries, hence once you are near a port of entry, tell the skipper of your Caribbean sailing charter to go to the custom officials and show the passports of all the guests, the crew list as well as the papers for the ship.


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