the Caribbean Sailing and Boating

Sea-savvy vacationers find sailing and yachting a great way to visit the Caribbean

Photo credit: © Pete Markham

Caribbean Sailing

The Caribbean region is known worldwide for its near-perfect sailing conditions; the water is always warm and there are plenty of beautiful islands to visit. Many people travel via yacht each year to take part in annual races or simply enjoy the winter sailing season.

Caribbean waters are steeped in legend: This area is the famed Spanish Main, and has been home to more than its fair share of pirates. From Sir Francis Drake and Sir Walter Raleigh to John Paul Jones and Henry Morgan, there are many treasure-seeking seafarers who long ago cut a swath through the island waters.   Vacationers can have their own adventures in the Caribbean Sea, whether aboard a party boat, a chartered yacht, or a day rental.

Party Boat

Caribbean travelers can get their sea legs by spending a short time at sea aboard a party boat.  Dinner and booze cruises fall under the party boat category, and in these instances visitors purchase tickets for an evening of food and fun.  Party boats can also be rented by vacationers for special events such as anniversary celebrations, wedding ceremonies, birthday parties, and product launches.  Depending upon the size of the boat, 30 to 300 guests can climb aboard, and are treated to several hours at sea, as well as such extras as a DJ and dance floor, food, and beverages.


Yachts are chartered from within or near the Caribbean on a nearly weekly basis, and the industry as grown in recent years to accommodate the number of vacationers who decide they'd rather sail to the region than fly. Your yacht rental options are bareboat, skippered bareboat, or a crewed charter.

If you're an experienced sailor, you may decide to charter a bareboat, a rental boat with all the equipment needed to travel the Caribbean, but with no crew. If you wish to rent a bareboat, you will need to prove your qualifications and you may be given a tutorial of the Caribbean area including reefs and safe harbors.  Voyage charters and demise charters are the two categories of bareboats.  On a voyage charter, the owner allows you to take full control of the boat, but remains on board as a passenger, while there is no supervision whatsoever on a demise charter.

Based on your knowledge and experience, the charter company may insist that you take a skipper for at least the first couple of days of your journey. However, if the company insists you travel with a skipper it does not mean they will be paying for his services. If you're not quite ready to set sail on your own, go with a skippered bareboat. A skipper lends his sailing knowledge and expertise to your Caribbean journey, and is paid by the day.

Crewed charter yachts come with a skipper and full crew including a cook. On a crewed charter, remember this: the captain is the one in charge of all things boat related. You can help to decide on the itinerary but, if weather or any other obstacle threatens this itinerary, the captain will alter the route for safety purposes.

Flotilla sailing is a fun option for large groups of experiences sailors traveling together.  Flotilla sailing is comprised of numerous boats sailing the same course to the same destination.  A hired captain with knowledge of the area is in charge of the lead boat, but members of your party skipper the other boats in the train. 

After deciding which type of charter is best for you, it is time to pick your boat.  Yachts and catamarans are the most commonly chartered vessels.

Yachts are luxury crafts that range in size from 20 to several hundred feet long.  The boat is comprised of one hull, and comes in multiple styles.  Dingies, pocket yachts, and cruises are just a few of the most popular choices.  Catamarans, on the other hand, have two hulls, and are designed for stability and comfort.  

On most charters you may choose between having the food provided by the charter company for an additional fee or buying it yourself before you set sail. Buying your own food may be a difficult task if you are not departing from a major island. Do remember that you will be responsible for feeding everyone on board, including the skipper and/or crew.

Charter Companies

Charter companies in the Caribbean come in all sizes. If it is your first charter it is recommended that you choose a larger company because there are fewer guarantees with the smaller companies. For example, if the boat you had requested becomes unavailable, smaller companies may not have other boats for replacement. On the other hand, larger companies will most likely give you a similar or larger boat in that situation at no extra cost. Many of the better smaller companies, however, purposefully stay small in order to provide higher customer service.

There are two tiers of charter companies that are not quality or service designations. In the first tier companies use the newest boats, often with the most extras. Boats older than four or five years are no longer used by first tier companies. First tier boats may include the auto pilot function, GPS systems, stereos, and cell phones; check with the specific charter company for details. Second tier companies usually use older boats from the fleets of first tier companies. These second tier boats come with fewer extras and a lower price tag.

The most popular large yacht charter companies currently serving the Caribbean region are The Moorings and Sunsail.

Charter Brokers

If you select a crewed charter, you'll want to make sure you're compatible with the crew. The best way to find the right crew for you is through a broker. Yacht brokers act similarly to travel agents, and they can often provide quotes from several different chartering companies. The boat owner pays for the services of the brokers, so you can utilize their help at no cost. Brokers can also help you find a bareboat charter.

There are two main charter broker trade organizations: the American Yacht Charter Association (AYCA) and Charter Yacht Broker's Association (CYBA). Members of the AYCA and/or the CYBA include the following outfits:

In the Caribbean:

Charter Broker Telephone Number
Crewed Charters (U.S. Virgin Islands) 800-874-2584
Mystic Man Tours (St. Lucia) 800-401-9804                                                                                      St. Lucia: 758 459 7783
Nicholson Yachts Worldwide (Antigua) 800-662-6066
Paradise Connections (U.S. Virgin Islands) 254-230-1491
Pro Valor Charters
(British Virgin Islands)
284-495-1931 (voice and Fax)
Regency Yacht Vacations (U.S. Virgin Islands) 800-524-7676
British Virgin Islands: 284-495-1970
Stewart Yacht Charters (U.S. Virgin Islands) 800-432-6118
Yates Yachts (U.S. Virgin Islands) 866-994-7245
Bonaire Sailing School


In Florida:

Charter Broker Telephone Number
Broward Yacht Sales Charter Division 954-763-8201
Charter Specialists 800-479-9054
DY Charters LLC 772-563-3326
Fraser Yachts Worldwide 954-463-0640
June Montagne Yacht Charters 954-217-2992
Marine Group of Palm Beach, Inc.. 561-627-9500
Nicely-Dunn Yacht Charters 800-874-0724
Paradise Yacht Charters 954-462-0091
Rikki Davis, Inc. 954-761-3237
RNR Yacht Charters 800-525-2526
Tom Collins Yachts Worldwide 800-637-5407
Whitney Yacht Charters, Inc. 800-382-9666
Yachtstore, Ltd. 888-376-5198
Lucid Yacht Group 954-650-7353

Sailing to the Caribbean

Before you set sail, be aware of safety issues. Coral reefs grow near some islands and the trade winds may be unfavorable.

Also consider these things when setting your ocean course:

  • The strongest currents and largest waves are most often on the northeastern sides of the islands, at the Atlantic Ocean.The waters of the Caribbean Sea are generally much calmer and make for easier sailing.
  • The best time of the year to sail in the Caribbean is from January through March, although this is near the Caribbean's peak tourist season so prices will be higher.
  • The summer rains and hurricane season, June through November, do not always make for easy sailing.
  • If you're inexperienced or a first time sailor your best experiences will likely be in the Virgin Islands or the Bahamas. These islands are near the U.S. mainland and can be an early stop on your journey to the Caribbean.

It is also important that you be aware of entry requirements for every country that you plan to visit.  Have documents such as passports for everyone on board, your crew list and declaration, the ship's registration, a list of the ship's stores, and departure permission from your last port of call on hand to present to customs.

Day Rentals

Not everyone wants to spend the bulk of their vacation on a boat.  These travelers have the option of renting yachts for several hours (or several days to use at their discretion) at a time.  They can then take their boat out for short sails, fishing trips, island tours, and water sports.  In this instance, the most common type of yachts to rent include waterski boats, family cruisers, runabouts, and cruises.  These vessels range in size, and can accommodate between five and 10 passengers.

Those interested in sailing to and around the Caribbean have plenty of options to choose from.  Whether you're looking for a few hours of fun on a party boat, a day of sailing on a rental, or an overnight adventure on a charter, sea-minded travelers will find that their perfect choice in charter yachts are available throughout the region.


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