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In addition to being one of Anguilla's most popular island pastimes, sailing is the island's national sport. Many vacationers enjoy participating in or simply observing this exciting water sport. The tradition of sailboat racing started years ago, when Anguillans returned from fishing trips and raced their boats home. From then on, the spirit of competition took over and created what is now the most popular sport in the Caribbean.
Anguilla hosts a number of annual sailboat racing events. Anguillans from around the world travel back home to the island just to be a part of these exciting events, which can be compared to mega-sporting events like the Super Bowl or World Cup. The racing season runs from May through August, so vacationers can join the locals as spectators from cliffside vantage points. These prized races are followed by post-race parties that can last into the wee hours of the night.
Some sailors and boaters are attracted to Anguilla's isolation, as well as the delightful bays on both the north and south coasts of the island. Boaters who seek some of the most private waters around Anguilla will discover heavenly solitude in the waters of the Prickly Pear Cays and Dog Island, which are just north of Anguilla. After clearing immigration, boaters can dock at Blowing Point and Road Bay, the island's main ports of entry. Be sure to clear your boat or yacht through customs properly; failure to do so could result in hefty fines or even confiscation of your vessel.
Caution
Sailors and boaters should always be cautious when navigating the waters of the Caribbean. Look out for coral reefs, especially around the island, which can do serious damage to your watercraft. Also, stay alert for unfavorable trade winds and storms that could be brewing over the water.
While sailing and boating, consider the ocean currents, which are considerably stronger in the Atlantic Ocean than in the waters of the Caribbean Sea. The season during which sail will also play a part in the conditions of the water. Hurricane season and heavy rains occur during the summer months, and less experienced boaters should avoid these sailing conditions.
Choosing a Charter
Vacationers can choose from several different kinds of boat charters:"bare boats,""skippered bare boats," and"crewed charters." Most charter companies have boats available by the week that can be chartered in the Caribbean or in neighboring areas.
More experienced and serious yachtsmen often choose"bare boat" charters, which come with just the boat and equipment, but no crew. Before chartering a bare boat, charter companies will require proof of your qualifications to navigate the vessel on your own.
If the charter company decides that you don't have enough experience or that you are not familiar enough with the waters surrounding Anguilla, they will offer you a"skippered charter." The company usually insists that the skipper accompany you for at least the first few days of your charter to assist you in getting to know the waters. You will be responsible for paying the skipper's daily rate, which doesn't include meals or a gratuity.
"Crewed charters" come with a captain and a full crew, including a cook. You can set the travel itinerary for the charter, but the captain will be in charge of everyone's safety and will ultimately make the decisions when it comes to navigating the ship. Therefore, if the captain thinks that the waters are too rough or that the weather conditions are too bad, he can choose to change the ship's course or even cancel the trip.
Some charters offer food and supplies. Brining your own food may be a cheaper, but less convenient, option. As the renter of the charter, you are responsible for feeding everyone on the yacht, including the skipper and the crew.
Charter Companies
Travelers can choose from two different divisions of charter companies when deciding on a charter. The first way to classify a charter company is by size. First time yacht charterers should opt for a larger charter company for several reasons. First of all, large companies offer more guarantees and will replace your boat at no extra charge if a particular charter suddenly becomes unavailable. Smaller charter companies keep their organizations small in order to provide better customer service.
Charter companies can also be classified as either first or second tier. These classifications are not related to quality standards, but rather to the age of their boats. First tier charter companies have the newest boats, stocked with the most modern equipment and technologies, like cellular phones and CD players. First tier boats are usually no more than 4 or 5 years old. Second tier companies have older boats, which they usually purchase from first tier companies. These older boats cost less than newer boats, but generally do not have all of the extras of first tier boats.
Charter Brokers
It is important to find a crew that is compatible with you and your travel expectations when chartering a crewed boat. Charter brokers are a good way to find a suitable crew. Brokers are also an excellent way to find the best charter rates on bare boats and skippered charters. You don't have to worry about the cost of the broker because the charter company pays for their services.
Two key organizations that help charterers pick qualified charter brokers are the American Yacht Charter Association (AYCA) and Charter Yacht Broker's Association (CYBA), which have members around the world.
Here are some charter companies in the Caribbean:
| Charter Broker | Telephone Number |
| Crewed Charters (U.S. Virgin Islands) | 800-874-2584 |
| Nicholson Yachts Worldwide (Antigua) |
800-662-6066 617-661-0555 268-460-1530 |
| Paradise Connections (U.S. Virgin Islands) |
877-567-9350 340-774-1111 |
| Regency Yacht Vacations (U.S. Virgin Islands) | 800-524-7676 284-495-1970 (BVIs) |
| Stewart Yacht Charters (U.S. Virgin Islands) | 800-432-6118 |
| Yates Yachts (U.S. Virgin Islands) |
866-994-7245 970-871-6002 |
In Florida:
| Charter Broker | Telephone Number |
| Broward Yacht Sales Charter Division | 954-763-8201 |
| Charter Specialists |
800-479-9054 305-852-9196 |
| 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 305-852-5136 |
| Paradise Yacht Charters | 954-462-0091 |
| Rikki Davis, Inc. | 954-761-3237 |
| RNR Yacht Charters |
800-525-2526 954-522-9563 |
| Tom Collins Yachts Worldwide | 800-637-5407 |
| Whitney Yacht Charters, Inc. | 800-223-1426 |
| Yachtstore, Ltd. |
888-376-5198 954-791-1737 |
Choosing a Yacht
Making a well-informed decision when chartering a yacht means considering your personal charter needs. The kind of yacht you charter will play a big part in the kind of vacation you will have. Here are some things to consider when deciding what kind of yacht to charter:
For the most comfort on your charter, go with a yacht that has one more cabin than you anticipate using. Families may want to consider chartering a catamaran because they have the most comfortable cabins, experience less roll than other vessels, and are generally safer for children.
The most popular bareboat charters are monohull yachts with three cabins and two bathrooms. These vessels range from about 36 to 50 feet in length. The drawback to these boats is that they have ply-wood walls, which carry sound very easily.
If you charter a large ship with a lot of extra amenities, expect to pay more for your charter.
Boats with canvases over the cockpit provide protection from the harsh rays of the sun.
When chartering a bareboat, don't expect a lot of extras like kayaks or electronic gadgets. If you want these items, inquire ahead about their availability.
Costs and Paperwork
While you're planning your charter, don't forget to consider the price of your excursion. Crewed charters are the most expensive kind of charters. In addition to the cost of the charter, you must also tip the crew about 10 to15 percent of the overall cost of the charter. Tips comprise about 30 to 50 percent of the crew's income, and should not be overlooked when budgeting for your trip. When getting a skippered charter, you'll have to pay the skipper's fee, which is usually about $80(USD) to $120(USD) per day.
Always read the small print on the charter company's paperwork. Sometimes charter companies add the cost of the deposit and insurance fees to the cost of the charter. Charterers should put all costs on a credit card to avoid any problems or mistakes. And remember, most charter companies do not refund travel within 60 days of the scheduled departure date.
Enjoy the beautiful waters of Anguilla on an exciting charter trip that's sure to create lasting memories of this beautiful paradise.