A teaching pro turned sailing captain launches charter trips in the CaribbeanFrom

With his suntanned legs and wide-brimmed hat, Tim Schaaf looks every bit the capable captain of his elegant forty-five-foot catamaran. But Schaaf, who owns and operates Jet Stream Sailing & Golf Charters, knows something about golf, as well. He was the head coach at Stanford University during the pre-Tiger era of the 1980s, and he’s a former PGA pro. He co-founded SyberVision Golf Schools, once ranked among the world’s top teaching programs, and helped develop a computerized swing analysis. He is also an iconoclast: As a PGA section officer in Maryland, he once pushed through a rule change allowing shorts to be worn in club-pro tournaments. At a college event in Hawaii, he had his Stanford players wear aloha shirts.

For two decades the Harvard-educated Schaaf, 60, has been chartering trips through the Caribbean from his home port of Virgin Gorda in the British Virgin Islands. This year, he’s offering a seven-day golf cruise. The first port of call is St. Croix, with rounds at Carambola Golf & Country Club, designed by Robert Trent Jones Sr., and the short and scenic Buccaneer Golf Course. From there, it’s on to the Puerto Rican island of Vieques for some beach time and snorkeling before golf at El Conquistador, a sporty Arthur Hills layout with elevated tees that provide views of El Yunque rain forest. Though he’s open to custom routes, Schaaf favors this itinerary because it’s mostly downwind, and he’s arranged special green fees, typically no more than $100.

When his captain’s duties allow, Schaaf will go ashore as a playing partner (at no charge) or teaching pro (about $300 per round). “This kind of trip is guaranteed to make you a better wind player,” he says, only half in jest.

The sleek catamaran accommodates up to six passengers in three cabins, each with air conditioning and a private bath. Gourmet dinners are provided nightly by Schaaf’s partner, Marsha McCoskrie, a professionally trained chef.