One of the most popular location for windsurfing on Grand Cayman is at East End at Morritts resort. There is a rental operation run by Red Sail Sports and Tortuga divers, where visitors can rent a selection of boards and sails, and also get lessons from windsurf instructors. In winter, the wind blows from the NE, so being at the NE most point of the island, the wind is strongest here. This spot is great for all levels of windsurfer. The sailing can be done inside a protected reef, for beginners and speed sailers. The channel offers a place for more proficient wave sailers to jump (starboard tack) and ride the waves.
During the summer months, the wind is more likely to come from the SE. For those who like flat-water blasting, the dock along South Church Street is the most suitable place to go. One thing to watch out for is the many mooring lines close to shore, which can cause a few heavy wipe-outs if you fail to spot them. Further South at by the community centre is a great place to go and get some small wave sailing in anything from an E to SE wind direction. This is a known surf spot, and can be very shallow. It is best to launch to the left (facing the water) of the community centre, as it is a bit deeper. Surfers will launch to the right and surf on the shallow reef. As a windsurfer, it is best to stay further out to the left so as not to remove a fin on the shallow reef or an arm from a surfer. There is a small island further out, which produces some nice waves to play on.
For those with a fair amount of endurance and stamina, a great launch spot is Starfish Point, which is a sandy outcrop near Rum Point. In a NNE wind one can head out to the sandbar and Stingray City from here. It is a bit of a journey, so you will find yourself doing fewer, longer sessions, as it is about 1.5 miles between the launch spot and the Sandbar. Once out at the Sandbar, there can be some large waves to play on in the channel, which makes the distance worth it.
At the end of Safehaven golf course, there is also a place to launch into the North Sound from. This is a convenient spot for the local windsurfers who can get a quick sail after work in the evenings before it gets dark. It gets fairly choppy here and there are some nice port tack jumps to be had.
A spot more suited to kite-boarders, as it is fairly shallow here. There is a small launch beach that one can launch into the North Sound from. From here you can also get to the main channel, Stingray City or the Sandbar, but it will require some tacking into the NE wind.
Seven Mile Beach
One of the most exciting places to sail, but only in a NW, which happens approximately once in a blue moon, or as often as the green flash at sunset! When this spot works, there are some huge ramps to jump and some great wave sailing to be had. The shore break can be rather feisty though, so make sure you time your entrance and exit accordingly.
Further up SMB, is a spot called Boggy Sands, which offers port tack jumping in a SE wind direction.