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. This private club sometimes offers lessons to nonmembers (CI$275) but always has boats, including lasers, Picos 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 Estate, 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 47-foot Beneteau, Splendour in the Wind, 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 $900, a full day $1,575 and up, which includes a deli-style lunch; if you have a large group, it's little more than the price for crowded excursions with twice as many strangers. Yacht Club docks B-48, D-15, and D-17, Seven Mile Beach, Grand Cayman. 345/916–4333; www.sailcayman.com.