Though Cayman has a large sailing community, it isn't a big charter-yacht destination. Still, you can skipper your own craft (albeit sometimes under the watchful eye of the boat's captain). The protected waters of the North Sound are especially delightful, but chartering a sailboat is also a wonderful way to discover lesser-known snorkeling, diving, and fishing spots around the island.
Cayman Island Sailing Club. Cayman Island Sailing Club is a private club that sometimes offers lessons to nonmembers (CI$275) but always has boats, including lasers and J-22s, for hourly or half- and full-day rental (CI$30–CI$300). They also feature windsurfing lessons. The club's a great hangout, and chatting up the friendly members provides invaluable insights into all subjects Caymanian. 320 Spinnaker Rd., and Selkirk Dr., Red Bay, Grand Cayman, KY1-1205. 345/947–7913. www.sailing.ky.
Sail Cayman. Neil Galway, an experienced RYA Yacht Master, runs Sail Cayman, offering 30-foot Gemini RIB ecotours and three seaworthy sailboats including the plush 45-foot Gibsea, the NautiGal, for full-day or half-day private sailing or snorkeling. Though not bareboating, it is hands-on: you can crew and even captain if you enjoy sailing. Neil personalizes the cruise to suit any family or group, accommodating a maximum of 12–15 passengers. A half day runs $600–$700, a full day $1,000–$1,200, which includes a deli-style lunch: if you have a large group, it's little more than the total price for crowded excursions with twice as many strangers. Yacht Club dock C-31, Seven Mile Beach, Grand Cayman. 345/916–4333. www.sailcayman.com.