Boating and Sailing Near the Cayman Islands

The Cayman Islands offer visitors fine sailing in un-trafficked waters

Photo credit: © BrianMKA

The Cayman Islands are not among the top-sailed islands of the Caribbean, in large part because of their location off the beaten path for sailors. However, this does not mean that the Caymans have nothing to offer sea-lovers. In fact, they have excellent underwater scenery that delights many visitors. In addition, the Caribbean itself is known worldwide for its incredible sailing.

Before you set sail, be aware of safety issues. Coral reefs grow near some islands and the trade winds may be unfavorable. Of course, the time of year is also a major factor to consider when sailing. Although the waters will be more pleasant from January through March, this is near the Caribbean's peak tourist season when prices are generally higher throughout the islands. July through November, however, bring the summer rains and hurricane season, which do not make for easy sailing.

If you're simply wanting to experience some time on the open water, without the complications and cost of sailing on your own you can take an excursion. Want to know more what's included and how long a trip lasts? See the listing that follows for information on area providers.

Boat Excursions
Name Phone Location
Cayman Islands Sailing Charters (345) 525-1222 10 Market Street - Georgetown
Jolly Roger (345) 922-9922 West Bay Road - Downtown Georgetown
Ocean Frontiers (345) 947-7500 Grand Cayman
Pirates Of The Caymans (345) 623-7245 West Bay Road - Seven Mile Beach
Red Sail Sports Charter (345) 623-5965 3.1 mi. (5.0 km) North of Georgetown
Sail Cayman (345) 916-4333 The Yacht Club C31 - Georgetown

Boat Rentals and Charters

If you're thinking about a boat charter, you can reserve one from these firms:

Charter and Rental Services
Name Phone Location
Cayman Islands Sailing Charters Ltd (345) 525-1222 Cayman Islands Yacht Club - West Bay
Mainstay Sailing (345) 927-1127 West Bay Road - Crystal Harbour
Mooremarine Services & Boat Rentals (345) 949-6672 62 Lincoln Road - Georgetown
Pro Yacht (345) 945-4676 Cayman Islands Yacht Club - West Bay
Stingray Cab an' Tours (345) 916-6247 184 Sitwil Drive - 1.6 mi. (2.5 km) East-Northeast of Bodden Town

Charter Companies

Charter companies in the Caribbean come in many different shapes and sizes.

First Tier

  • These companies only use ships until they are 4 or 5 years old.

  • Ships in these companies usually have the most electronic extras.

Second Tier

  • These companies often buy ships from first tier companies.

  • They are older boats, with fewer electronic extras.

  • These are less expensive to charter.


  • Recommended for first-time charterers.

  • Have more ships, and are better able to handle problems if ships are unready.


  • Usually offer top-notch customer service.

  • Have much smaller fleets.

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

Charter Brokers

Charter brokers can help vacationers pick the right ship and crew for their journey. Whether you're trying to make sure your personality matches with the crew, or just trying to find the ship with the most amenities for the lowest price, a charter broker can help. They represent many ships and companies and their services are paid for by the ships' owners.

The Charter Yacht Broker's Association (CYBA) and American Yacht Charter Association (AYCA) are two of the most common charter brokers associations. Members of the AYCA and/or the CYBA include the following outfits:

In the Caribbean:

Charter BrokerTelephone Number
Crewed Charters (U.S. Virgin Islands) 800-874-2584
Nicholson Yachts Worldwide (Antigua) 800-662-6066
Paradise Connections (U.S. Virgin Islands) 877-567-9350
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

In Florida:

Charter BrokerTelephone Number
Broward Yacht Sales Charter Division 954-763-8201
Charter Specialists 800-479-9054 
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. 800-223-1426
Yachtstore, Ltd. 888-376-5198

Choosing a Charter

Yachts are usually chartered from within or near the Caribbean on a weekly basis. Your yacht rental options are "bareboat," "skippered bareboat," or "crewed charter."


When chartering a bareboat, keep these factors in mind:

  • A boat that is captained and crewed by its charterers.

  • Charterers must prove their qualifications.

  • Charterers may receive an area tutorial, giving them knowledge of reefs and safe harbors.

Skippered Bareboat

  • Chartered by vacationers who know about sailing, but want an extra hand.

  • Requested by charter companies for less experienced vacationers.

  • Travelers always pay for the cost of the skipper, who is paid daily.

Crewed Charters

  • Includes skipper and full crew, including cook.

  • You may determine the itinerary, but the captain is in charge.

  • Routes may be altered to avoid bad weather and other obstacles.

Most charters will offer travelers the option of having food provided by the charter company for an additional fee. Though this is not the least expensive way to stock your ship, it does eliminate many of the hassles associated with transportation and purchase of food. Remember: You'll be responsible for feeding everyone onboard.


While the majority of ports are located on Grand Cayman island, there are two ports of entry for the Cayman Islands. One is in George Town on Grand Cayman and the other is at Creek on Cayman Brac. Though facilities are limited, travelers may stop in at any of the islands during their stay. Boats must be cleared in and out of every island.

Traveler's Tip: Officials are known for sticking quite closely to the rules. To avoid any unnecessary fines, make sure you're up-to-date on all of the procedures before visiting these islands.

When arriving in the Caymans, travelers must first contact Port Security on VHF Channel 16. This channel is monitored 24 hours a day. The Port Security will notify customs and immigration of your arrival, and will keep you informed of yacht boarding procedures. As soon as you have entered Cayman territorial waters, you must fly the Q flag. Mosquito control officers nearly always spray boats for a charge of $25(USD) before boats may enter the islands.

No guns, spear guns, or other weapons are allowed into the islands. These must be left with customs. Fruits and plants are also not allowed into the islands. Be aware that there are many restrictions regarding sailing.

The Cayman Islands are known for the diversity of their marine life, and officials work to protect the natural beauty of the islands. Since much of the sea around the islands is classified as a Marine Park or Environmental Zone, take care when traveling the area. No marine life may be taken inside such protected areas, but fishing is allowed outside of these areas. Due to restrictions, fixed moorings are the most prevalent way of anchoring, especially for yachts.

Other restrictions include the following:

  • There are rules against damaging coral with anchor chains.

  • Travelers are not allowed to remove marine life, coral, or sponges.

  • Spear guns and seine nets may only be used in certain areas and when licensed from the Cayman Marine Conservation Board.

  • Use of gill nets and poison is prohibited when fishing.

  • No dumping is allowed ; yachts must use a holding tank.

  • The following rules apply to fishing for lobster, conch, and grouper:

  • Only spiny lobsters may be taken, and the tail must be six inches. The limit is five per person or 15 per boat, whichever is less. Lobsters may only be taken from August 1 through January 31.

  • No more than 20 conch may be received from Cayman waters each day, with a catch limit of 15 per person or 20 per boat per day, whichever is less.

  • Remember that grouper spawning occurs in protected areas off of each island.

If visitors are caught breaking any of these regulations there is a maximum fine of $5,000(USD). Authorities may also order the confiscation of boat and equipment. Protected areas are marked.

Are you going to visit the Cayman Islands using a vessel you own, or a charter from a different location? This table lists places where you might be able to dock.

Name Phone Location
Cayman Island Sailing Club (345) 947-7913 320 Spinnaker Road - Georgetown
Cayman Island Sailing Club -- 2.7 mi. (4.4 km) East of Georgetown
Morgans Harbor Marina -- West Bay
Safe Haven Dock -- Crystal Harbour
The Barcadere Marina (345) 949-3743 606 North Sound Road - Georgetown


Chartering a yacht will cost you more during the high season than during the off-season, and on-island costs will be higher during high season as well. Travelers picking up a yacht on the islands or far from home will need to account for airfare. Don't forget to make customs duties and possible luggage fees a part of your charter budget.

Costs can be divided into crew, amenities, size, and type:


  • Crewed charters are more expensive than bareboat charters

  • Crews should be tipped 10 to 15 percent of the charter cost: this makes up 30 to 50 percent of their income

  • Skippers, if chartering a skippered bareboat, are paid at a rate of about $80(USD) to $120(USD) per day.

  • Food costs will also be higher when feeding a full crew.



  • Ships with more amenities are usually more costly.

  • Crewed charters usually include more amenities.

  • A power windlass can be an invaluable addition for help in anchoring.

  • Many travelers like to have a canvas top over the cockpit to help prevent sunburn.

  • Kayaks, windsurfs, GPS, and other extras may not be widely available on bareboats, but can often be added for a fee.


  • Larger ships are generally more costly.

  • Most travelers prefer a ship with one more cabin than they intend to use.

  • Three cabin/two bath monohulls are the most popular size and style. These range from 36 to 50 feet.


  • Monohull boats are known for their thin, plywood walls that are far from soundproof.

  • Experienced sailors often prefer monohull boats.

  • Catamarans are preferred ships for first time sailors, those who experience seasickness, and families with young children because they experience very little roll in port.

Remember: You'll need to read the fine print on anything you sign. Additional insurance and deposit costs may not be listed, and travelers will want to make sure they're aware of the company's cancellation policy.\

Those interested in sailing to and around the Cayman Islands can find their perfect choice in charter yachts available throughout the region.

Your sailing experience in the Cayman Islands can differ depending on what your final destination is. See the links below for local sailing information for the three main Cayman islands.

Sailing in Specific Areas
Guide to Cayman Brac Sailing
Guide to Grand Cayman Sailing

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