Jamaica Sailing Cruise Vacation: Beyond The Tourist Traps

While its dazzling white beaches are not much different from those you will find on a dozen other Caribbean islands, Jamaica’s remarkably dense tropical landscape and soaring Blue Mountains, with their perfect coffee-growing terrain, has far more than the sun, ocean, and sand, to recommend it as a cruise destination.  Jamaica has more than 100 rivers plunging and tumbling from their mountain sources on their way to the sea, miles of hiking and equestrian trails, and jungle canopy tours to appeal to the most adventuresome cruise enthusiasts.

Jamaica’s beach resorts are, of course, its most popular tourist destination.  Seven Mile Beach at Negril, on the island’s westernmost point, is famous for its rugged cliffs and unforgettable sunsets.  Negril, however, lacks a harbor, so your sailing cruise ship will have to leave from one of Jamaica’s three ports-of-call.

Jamaica’s northern coast is where you find Mo’ (for Montego) Bay and Ocho Rios, its two busiest resort towns.  Montego Bay is home to the "Hip Strip," formerly known as Gloucester Avenue, where you will find plenty of shops, restaurants, and clubs.  If you want a natural healing experience, you could head for the mineral springs at Montego Bay’s Doctor’s Cave Beach.

A more family-friendly port-of-call, Ocho Rios is home to one of Jamaica’s biggest craft markets, along with an abundance of duty-free shops and a generally more relaxed lifestyle.  Perhaps the most stunning of all Jamaica’s three ports-of-call, however, is its smallest one.  Port Antonio, on Jamaica’s north east coast was, in days gone by, a magnet for Hollywood elite and the favorite hideaway for Errol Flynn.  

Far removed from its three most popular ports of call is Jamaica’s capital city of Kingston, which is also the largest English-speaking city in the Caribbean.  Jamaica has a rather turbulent history, beginning with its reputation for harboring pirates centuries ago.

Most Jamaican sailing cruises are scheduled between January and March, which is also Jamaica’s peak tourist season.  You probably will not be able to book a Jamaica sailing cruise between July and November, when the heat, heavy rains, and possible cyclone conditions make it too dangerous to sail.

When making arrangements for your Jamaica sailing cruise, pay attention to the legal details.  Once you have reached Jamaica, you will have to let customs know that you have arrived and give them access to your ship for inspection.  They will ask you, or whoever is managing your Jamaica sailing cruise, to supply information which includes your cruise ship’s registration, team list and affirmation, a record of the ship’s stores, and your departure permission. While many amateur sailors arrive at Jamaica in their own yachts, the great majority of tourists taking Jamaican sailing cruise vacations simply rent their boats.  Most of these sailing cruises last between seven and 10 days, departing from Montego Bay, the site of Jamaica’s airport. Negril, however, is another ideal departure point for a Jamaica sailing cruise.

You have a choice of three different types of ships for your Jamaican sailing cruise.  There are crewed charters, skippered bareboats, and, if you are an accomplished sailor, bareboats.  If you’re new to Jamaica, getting a skippered or crewed boat will ensure that your sailing cruise hits the largest number of attractions.  Having a crew on board will also give you as much free time as you like to enjoy Jamaica’s remarkable beauty!