Windy City

<< Back to Robb Report, September 2014

A new nautical program introduces aspiring sailors to the Newport way of life. 

Ready about!” I yell into the wind, my hands sweaty and hot as they grip the wooden tiller at the Privateer’s aft.

“Ready!” answers my guide, Mary Finn, with the customary sailor’s response.

I push the tiller in the direction of the mainsail, leaning with my back to the wind until I am bent like a bodybuilder in mid-squat. Leaning, leaning, leaning, the starboard side begins to dip into the water, and for a split second I envision floating down Narragansett Bay in my life jacket. But just in the knick of time, the mainsail whips over my head and blows up like a balloon in the wind. I immediately swing over to starboard, prop myself on the edge of the boat, and right our course with the tiller.

“You look like you’ve been doing this your whole life!” Finn shouts. The compliment, hyperbolic though it may be, means a lot coming from a Newport, R.I., native and a 40-year sailing veteran. Finn, an instructor at New England’s largest public sailing center, Sail Newport, took up the sport at the age of 10, inspired by the colorful boats that passed by her family’s beach cottage on Castle Hill Cove. “Newport is the sailing capital of the world,” she says as a group of children effortlessly coast by us in miniature versions of our J/22 watercraft. “In the summer, there are more people in the harbor than on the streets.”

Last May, Sail Newport partnered with Castle Hill Inn—a 35-room Relais & Châteaux property located on the same 40-acre peninsula where Finn spent her childhood summers—to create the two-night Sailing Escape experience. Designed for aspiring sailors, the package (available May through October and priced from $1,758 to $3,489) includes a one-on-one clinic with the experts at Sail Newport, in which guests learn the basics of helming a 22-foot sailboat. Off the water, participants can relax on the resort’s private beach and dine on Georges Bank scallops and Maine lobster at its restaurant.

After three hours of jibing, tacking, broaching, and feathering with Finn, I return to Castle Hill Inn slightly sunburned and completely exhausted. I am tempted to settle in for the evening at my shingled beachfront cottage, but I instead stroll to the resort’s 19th-century mansion for a cocktail on the manicured lawn overlooking Narragansett Bay. From my Adirondack chair, the breeze feels much gentler and the waves appear much calmer than they did during my afternoon adventure. Just as the sun rests on top of the horizon, a striking sailboat more than five times the size of the Privateer comes into view, leaning, leaning, leaning ever so elegantly into the wind.

Castle Hill Inn, 888.466.1355, www.castlehillinn.com 

The mountainside property now has a multilevel spa and five new suites…
FREE PREVIEW: Aman Tokyo is among Robb Report’s 2015 Best of the Best selections…
Destinations include Napa, New York, Paris, London, and Milan…
Be among the rare few to visit a sumo stable, or experience Kabuki and dine with the performers…
From romantic suites to a new restaurant, the Caribbean resort
The private charter company gives passengers an unbelievable deal on holiday travel...
The Irish castle unveiled a complete remodel of all 28 guestrooms in the Queen Anne wing...
The updated Southern California resort features plush new décor and state-of-the-art amenities...
For nearly $100,000 per night, guests receive exclusive access to the hotel and its amenities...
From private beach excursions to walking tours, Palazzo Margherita offers ample summer activities...