Cayman Islands Sailing

Grand Cayman Stingray Sandbar & Reef Sail

Online Reservations

Visit the exciting Stingray Sandbar where you can snorkel and play with Cayman's amazing southern stingrays. Discover spectacular coral, friendly fish and breathtaking views throughout this unforgettable experience aboard a luxury catamaran.

Welcome to the inviting waters and white sand beaches of Grand Cayman. Enjoy the beautiful warm days and nights in this exotic paradise. Grand Cayman is the best known dive destination in the Caribbean, if not the world.

The water is warm and crystal clear year round. There are stretches of magnificent, unspoiled coral reefs, schools of colorful and friendly fish, spectacular shipwrecks, vertical walls and dramatic underwater drop-offs.

There is no better way to discover the amazing underwater world than aboard a luxury catamaran. This three-hour cruise will take you to the famous Sandbar where you can play with Cayman's amazing Southern Stingrays standing in two to four feet of water.

A full cash bar and snacks are provided. Snorkel equipment is included if required. The catamaran is approximately 65' long and features plenty of cabin space, trampoline nets for sunbathing, ample shade and restroom facilities.

This tour promises an exciting and relaxing way to discover the natural beauty of Grand Cayman. For families and nature lovers alike, this cruise is a must do when visiting the Cayman Islands.

Departure Point: Tour departs from the Safehaven Dock

Departure Times
Monday, Wednesday and Friday: 1:45 pm
Saturday: 1 pm
Thursday: 9 am
Return Details: Returns to original departure point at approximately 5 pm

Grand Cayman Catamaran Dinner Cruise

Online Reservations

Dine under the stars with your loved one on this romantic evening cruise. You'll enjoy exquisite Caribbean cuisine and gorgeous sunset views on a voyage you'll remember forever.

The adventure begins with a sunset sail, refreshed by your favorite cocktail. Cruise along the turquoise waters as you and your admirer share an experience of a lifetime.

The catamaran then anchors for a three-course, gourmet candlelit dinner with a variety of Caribbean themed entrees. Top off the evening with a delicious local coffee.

Departure Point: Departs from the Seven Mile Beach Watersports Center

Departure Times
Winter - 5.30 pm
Summer - 5.45 pm

Return Details: Returns to original departure point at approximately 8:45pm

Jolly Roger Cruises

Sunset Cruises
The sunsets and night skies of Grand Cayman are nothing short of spectacular and there is no better way to enjoy them than aboard the Jolly Roger. This two-and-a-half-hour cruise is a perfect start to a memorable evening.

The journey begins with complimentary rum punch and appetizers. As with all good pirate ships, she sails with a well-stocked bar of brand name spirits for the perfect cocktail. Cruise along beautiful Seven Mile Beach and enjoy a little Cayman magic. Throughout your cruise you will enjoy a large variety of music ranging from Reggae, Salsa and Calypso, to the top ten hits of the 80's and 90's. You can dance the night away or just savor the experience.

On the Sunset Cruise there is an open bar, and you can choose between having just appetizers or a full dinner consisting of appetizers, entree and dessert.

Private Cruises
In the 17th century, Grand Cayman was famous for being a safe harbor for pirates and their treasure. Today, many Caymanians are direct descendants of pirates. The Cayman Pirate encounter is a two hour coastal cruise that will take you back in time to the days of the pirate.

Sip rum and fruit punch as you watch traditional pirate antics being played out right in front of your eyes. Witness the Pirate Trial which ends in a fearsome sword fight. Don't forget to bring your swimsuits and snorkeling gear so you can explore the crystal-clear Cayman waters during the swim stop, with its spectacular reefs teaming with exotic sea life.

This cruise is great for kids who can fire the cannon, help hoist the mainsail, and make their brother or sister walk the plank at the end of a very blunt sword.

Cayman Islands Sailing Club - We have brand new top-of-the-line sailboats for hire. Give us a call and we'll have it rigged and ready to go.

Members of the Sailing Club receive half off all rental prices.

Red Baron Charters

Cayman Islands Sailing Packages
The Cayman Islands (which are located in the Caribbean Sea) offer tranquil holiday accommodation, from which you can depart on daytime excursions into the azure waters of the Caribbean. We offer a variety of sailing packages which will give you the chance to enjoy these tropical waters from the vantage point of a small powerboat or a sailboat, and even enjoy viewing some of the exciting wildlife which inhabits the Caribbean, as both half-day and full-day packages typically include two snorkeling stops in areas where there are many underwater animals to see.

Enjoy our Grand Cayman Excursions
The absence of rivers on Grand Cayman Island is largely responsible for the supreme clarity of the surrounding sea. When you take one of our Grand Cayman excursions, you will be able to enjoy a leisurely boat trip lasting hours, with skilled crew on board making sure that your boat trip is as safe as possible. In addition to our half and full-day excursions, you can also opt to go on a sunset sail which will give you the opportunity to view a spectacular tropical sunset from a boat on the sea, where your view will be unobstructed.

Grand Cayman Islands Sailing Bookings
You can make bookings for a Grand Cayman Islands sailing excursion via a link on our website. Our normal charter times for our half day trips are from 9 am to 12 pm, and 1 pm to 4:30 pm, and there are different rates depending on the size of your group booked for a specific package. Our full day trips last for two hours longer than our half-day excursions and in addition to the features offered in our half-day package, the full day option includes a Deli-style lunch. Our full day package has only one departure time usually, also at 9 am.

Snorkeling with a Grand Canyon Stingray Charter
When you take a Grand Canyon stingray charter with one of our packages, you will be able to visit Stingray City in the Caribbean Sea, where there are many of these exotic animals for your viewing pleasure. In some cases, our excursions can be customized and varied so that you may be able to obtain a different departure time if it is necessary in order for you to be able to make your booking. Snorkeling stops may also be varied, according to your needs. These changes are subject to our schedule allowing them, however.

Book a Stingray City Private Charter
If you want to enjoy a day on the surf with only your loved ones and/or a close few friends, you can easily book a Stingray City private charter which will allow you your intimacy and privacy during your sailing experience. You can view the specifications of our boats on our webpage – sufficient to say that our boats are of prime quality and will offer you a safe and comfortable trip across the clear, dazzling waters surrounding the Cayman Islands. If you are in need of accommodation on the islands, you can follow our links to accommodation offers.

Red Sail Cayman - From the first moment you step aboard a Red Sail Sports vessel in the Caribbean, you'll be greeted by only state-of-the-art equipment. Plus, you'll enjoy a warm welcome from a friendly crew whose sole purpose is to provide service, satisfaction and more service.

The catamarans are mastered by their crew, 365-days a year. Each member of the Red Sail Sports sailing and scuba staff has a different story and each person contributes to the success of the Red Sail Sports product.

The Ppalu, Poseidon, Cayman and Calypso are designed with the comfort of our guests in mind. The catamarans were built in the U.S. Virgin Islands by Gold Coast Yachts. They feature plenty of cabin space, trampoline nets for sunbathing, ample shade and restroom facilities. Sail times may vary, so please check with the dive shop/concierge on arrival. The catamarans may be chartered for special occasions such as weddings, birthdays, private dinners, groups or corporate meetings.

Stingray Sailing

The Tour
Our trips are done on the sailing catamaran, Far Tortuga. Far Tortuga is forty-three feet long and twenty feet wide. What does this mean to the average person? Space, and lots of it. With trips averaging a max of twenty five people there is always lots of room aboard Far Tortuga. Instead of sitting on a bench rubbing shoulders with the person next to you, we give you space to lay out in the sun to work on your tan.

The Sandbar
Once at the Sandbar, one of our crew will teach you the proper technique for interacting with the stingrays, then enter the water with you to show you how it is done. We will even supply you with squid (the favorite food of the rays) so that you can feed them and even tempt them up to the surface yourselves.

The Reef
After the sandbar we will head off to snorkel the reef. At This this location the water is between 6 to 8 feet deep, with the reef coming up almost to the surface. While swimming here you will see many kinds of coral and an abundance of tropical fish.

The Sail Back
Once you are done with that, we raise the sails for a quiet and relaxing trip back to the yacht club. In addition to creating lots of room the twin hull design provides a smooth ride by cutting effortlessly through the waves of the North Sound. For your convenience our boat is equipped with a fresh water rinse, to get the salt off, and a marine toilet.