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Red Sail Sports is a full-service Destination Management Company, offering guests a wide variety of leisure activities as well as transportation, restaurant dining and special events. We provide our guests with experienced, professional and friendly staff, quality equipment, and an assortment of exciting island activities. Red Sail Sports is also the largest watersports operator in Grand Cayman, with the resources to provide corporate or incentive groups of any size with first class facilities, including four deluxe 65' catamarans, custom-built dive boats, and an impressive selection of watersports equipment. Red Sail Sports will work with your hotel event manager to plan a creative and professionally implemented program for your group. If it can be done in the Cayman Islands, Red Sail Sports can do it for you!

Download 2019 DMC Brochure


Site Inspection 

Your Red Sail Sports Sales Manager will organize your familiarization trip so that you can experience a wide range of activities and restaurants. We will arrange round-trip airport transfers, provide you with an orientation tour of the island, and show you selected restaurants for dine-around evenings and group dinners. Let us make arrangements for you to experience activities, including a sail on one of our 65-foot luxury catamarans, and assist you with any other pre-program details.


Hospitality Desk

A Red Sail Sports representative can be available at your hospitality desk to assist your corporate or incentive group with restaurant reservations, golf tee times, scuba diving, watersport arrangements, and to provide a wealth of information about the island.



Red Sail Sports can arrange all of your transportation needs to ensure timely and efficient transfers. The buses are air conditioned, clean and well maintained by professional staff. Vehicles of all sizes are available to meet your group's needs.


On-Island Group Coordinator

If you are unable to join your group in Grand Cayman or if you would like assistance, a Red Sail Sports representative will take over the operational details of your program. Let Red Sail Sports continue the excellent service you have provided to your guests by being your On-Island Group Coordinator. We will greet your group at the airport, communicate with the hotel front desk to confirm your flight arrival and departure details, be on-site with your hotel's catering manager for all functions at the hotel, host off property functions, and be available to guests for any questions they may have.


Decor & Decoration

Red Sail Sports recommends Celebrations for decor and decoration. Celebrations are the only full-service event, wedding planning and Production Company in the Cayman Islands. They've designed and produced thousands of fabulous incentive group events. Their event planners are fastidious in their planning techniques, leaving no stone unturned. Their design team covers every aspect of your event production. Sound and lighting technicians work in close collaboration with set and event designers to create that special ambiance to compliment any and every event under the (Caribbean) sun!


Catering Services

Grand Cayman is known as the culinary capital of the Caribbean and as such dining options are limitless. Red Sail Sports can find catering options to suit any event, taste or budget.



Look to Red Sail Sports to organize and supply your welcome amenities, corporate gifts, custom logo applications and remembrances inherent to the island. Popular amenity programs include T-Shirts, hats, sunglasses, picture books, sun tan lotions, photo frames, prints and local artisan products.


Photo & Video

The Red Sail Sports Photo and Video Department is exclusively operated by Caribbean Producer Services (CPS). CPS has been operating in Grand Cayman since 1990 and has provided photo and video support to the Red Sail Sports DMC for several years. In addition, CPS assisted in film support to movies, numerous TV commercials and international and local group activities.