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While Puerto Rico is hardly the Caribbean's top sailing destination, it's got plenty of reasons for sailors to seek it out. Near the Virgin Islands, travelers find themselves near some of the finest sailing in the Caribbean, and, of course, in the Caribbean vacationers are never far from beautiful blue waters.
Before setting sail on your journey to Puerto Rico, familiarize yourself with some safety tips.
Avoid coral reefs, often found near islands, and be careful of Trade Winds, which may be unfavorable.
The northeastern side of Puerto Rico, facing the Atlantic, will usually have the strongest currents, while smoother sailing will be found on the Caribbean side.
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 on the islands. However, summer travel can be difficult due to rains and hurricanes.
Ports of Entry
There are several ports of entry for Puerto Rico, however, sailors should be aware of the island's unusual status as a Commonwealth of the United States. Despite its political affiliation with the U.S., travelers sailing to Puerto Rico from the U.S. must still gain clearance from customs. Since September 11, 2001 there have been some changes to the security measures for port entry into the United States and its territories.
Boats arriving from outside of Puerto Rico's territorial waters should contact Customs 24-hours ahead of time at any of the following telephone numbers:
| Location | Hours | Phone Number |
| San Juan | Monday - Saturday: 8:00 a.m. to 12:00 p.m. 1:00 p.m. to 5:00 p.m. |
787-729-6850 787-729-6802 |
| Fajardo | Monday - Saturday: 8:00 a.m. to 12:00 p.m. 1:00 p.m. to 5:00 p.m. |
787-863-0950 |
| Mayagüez | Monday - Saturday: 8:00 a.m. to 12:00 p.m. 1:00 p.m. to 5:00 p.m. |
787-831-3368 |
| Ponce | Monday - Saturday: 8:00 a.m. to 12:00 p.m. 1:00 p.m. to 5:00 p.m. |
787-841-3130 |
| U.S. Customs Service (after hours) | After business hours, Sundays, and holidays | 787-253-4538 |
Non-U.S. residents must obtain a visa for entry to Puerto Rico, as they would for entry into the U.S. Travelers should request a multiple-entry visa when traveling from the U.S. Virgin Islands or other U.S. territories.
Sailors may pick up a free 12-month cruising permit in the U.S. Virgin Islands. If you do not get one there, you will have to buy one when you arrive in Puerto Rico. The cost is $37(USD) for non-U.S. ships and $25(USD) for U.S. ships. This fee exempts sailors from other customs charges for one calendar year. Overtime fees will be charged outside of the working hours 9:00 a.m. to 4:00 p.m. Monday through Saturday.
Choosing a Charter
Chartering a boat leaves travelers with a few options. Experienced sailors may wish to charter a"bareboat", while others would prefer a"crewed charter." An option for sailors who want to have the chance to try their hand at sailing the Caribbean but aren't experienced is to book a skippered bareboat.
If chartering a bareboat travelers will often be required to show credentials, and may be given of the Caribbean area. Some companies may, based on a traveler's experience, insist that they hire a skipper for at least the first couple days of their journey. This can also be a help if travelers are unfamiliar with the region.
Chartering a crewed boat means you'll have captain and crew, including a cook - you can sit back and relax. However, remember that the captain has final say. If anything, such as inclement weather, should come up to cause problems with the intended itinerary, the captain will need to change the plans. He or she can help you find a suitable itinerary.
Many charter companies also offer passengers the ability to have food provided by the charter company for an additional fee. While this may be more expensive than providing your own food, it will often be more convenient. However, should you provide your own food remember that you will need to feed the crew as well as yourselves.
Charter Companies
There are plenty of different charter companies serving the Caribbean. To help differentiate between them there are a couple of classifications. Larger companies and smaller companies alike offer travelers most of the same services. However, smaller companies often choose to stay small to promote a closer company-customer relationship, while larger companies may have the best ability to care for the customer in the event that, for example, a ship suddenly becomes unavailable. The larger fleet of larger companies more easily provides a replacement ship.
Companies can also be defined by their"tier." A first-tier company has the newest boats, often with the most extras - but don't be confused by the name, tiers have nothing to do with a company's quality or service. These first tier companies do not use boats older than four or five years. Usually second tier companies pick up these older boats from first tier companies, but these second tier shops tend to have fewer extras and a lower cost. The two most popular of the larger charter companies are The Moorings and Sunsail in the Caribbean region.
Charter Brokers
Charter brokers act as travel agents for vacationers looking to find a yacht. The boat owner pays for the services of the broker, so all travelers have to do is contact the broker and they'll be on their way to finding the best yacht for them - and often times the best crew as well. Finding the best crew for you can be extremely important, you'll be spending your vacation with them.
There are two main charter broker trade organizations: the Charter Yacht Broker's Association (CYBA) and the American Yacht Charter Association (AYCA). Members of the CYBA and/or the AYCA include the following outfits 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 340-775-0010 |
Members of the CYBA and/or the AYCA include the following outfits 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
When choosing a yacht, the first consideration you need to make is for your budget. The larger the ship, the more costly your charter will be. The more people you travel with, the larger your yacht will need to be to accommodate those onboard, but the more people with whom you can split the cost. The most popular bareboat size is three cabin/two bath monohull, which ranges in size from 36 to 50 feet. Before choosing a large bareboat charter, think about your skill level. If you're confident with your skill and the skill of your crew, which should be larger when considering larger boats, you can consider any size of boat.
Where comfort is concerned, you may not want to make allowances. It's generally suggested that you charter a boat with one more cabin than you are expecting to use. Further consider that monohull boats have thin plywood walls that allow most sounds, including conversations, right through. If you're looking for privacy you will probably want to look elsewhere.
Catamarans are very different boats than monohulls, and can be nicer for those who are first time sailors, prone to seasickness, or nervous about long boat rides. These are better for families chartering a yacht for a vacation while monohulls are better suited to sailors who enjoy the experience of being at sea. Catamarans do not experience as much roll in port, and can be safer for young children. They can also have more comfortable cabins.
There are a few pieces of equipment that you may want to consider for your trip. Many charter companies and boats have a power windlass available to help you anchor, and these can be invaluable. Canvas tops over the cockpit can be necessary to prevent burning in sunny locales. Bareboats will not always have kayaks or windsurfs, and these may cost extra. Keep in mind that the boat you charter may also have the electronic extras mentioned earlier, such as GPS and CD players, and ask your company what your boat will have.
Costs and Paperwork
There is another difference between crewed yachts and bareboats, and that is financial. Bareboats in general cost less than a crewed yacht, and the crew must be tipped. A few items can effect the cost of such a charter.
Extras, like kayaking and scuba equipment, are often provided on crewed charters without any extra cost. However, crew tips, approximately 10 to 15 percent of the total charter cost, can make up a large addition to your total cost. These tips make up approximately 30 to 50 percent of the crew's income, making them an expense not to be overlooked. Skippers on bareboats can also be a substantial addition, as each skipper has his own daily fee, usually between $80(USD) and $120(USD).
While crewed charters do include a chef to prepare your onboard meals, you'll also need to plan to feed all the people onboard. This can be costly when buying food directly from the charter company, but travelers can't bring fresh fruit and vegetables into the Caribbean. While finding food in Puerto Rico is certainly easy, this may not be the case if you're starting from a smaller island.
High season costs are higher throughout the Caribbean, whether you're on Puerto Rico or any other island. Because of this, not only do the prices of charters rise, but so do the costs of airfare for travelers picking up their boats on the islands, and souvenirs will be more costly as well. And of course, don't forget customs duties and even luggage fees.
Traveler's Tip: When signing anything, be sure to check on the fine print. If there are deposit and insurance fees added to your charter cost you'll want to be well aware. Put any extra charges on a credit card to avoid problems if any mistakes are made. And check into a company's cancellation policy: most charters cannot be refunded less than 60 days before departure.
Those interested in sailing to and around the Caribbean can find their perfect choice in charter yachts throughout the region. Puerto Rico makes an interesting stop on your sailing itinerary.