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Enjoying Newport on a Charter Sailboat

For centuries people sought and found relief from summer heat and humidity in New England’s picturesque coastal towns. A perennial favorite is Newport, R.I., which also likes to be called “America’s First Resort.”

For centuries people sought and found relief from summer heat and humidity in New England’s picturesque coastal towns. A perennial favorite is Newport, R.I., which also likes to be called “America’s First Resort.” As the former host of the America’s Cup, Newport also carries the sentimental distinction as “America’s Capital of Yachting.”

But the glory days of the Golden Age of Yachting and the America’s Cup are long gone, forcing the town to reinvent itself as a tourist destination. Granted, the attractions are varied and numerous: the International Tennis Hall of Fame, the Cliff Walk, the mansions along Bellevue Avenue, the scenic Ocean Drive, the International Yacht Restoration School, and historic Fort Adams to name a few. But first and foremost, Newport is a sailing town, and taking a spin on Narragansett Bay under canvas is the best way to see it from its prettiest side.

If you live too far away to see it aboard your own boat, several outfits offer scheduled daysails during the warm season or charter trips by previous arrangement. Convenient locations along the waterfront and comfortable boats make this form of entertainment equally well suited for landlubbers, families with small children, or wannabe sailors who are in town without access to a boat.

Lovers of varnished spars and classic looks will gravitate toward the schooners Adirondack II and Madeleine, both docked in close proximity at Bowen’s Wharf. Although operated by different companies, both were designed and built by Scarano Boat Building in Albany, N.Y., a yard that also built replicas of Christopher Columbus’ caravel Santa Maria and the schooner America.

Adirondack II, a sister ship to the Adirondack that’s operating from Chelsea Pier on the Hudson River in New York, was launched in 1994 and is owned and operated by Scarano Boats. Why does a boatbuilder run a charter operation?“It gives us good exposure,” Rick Scarano explains. “It’s also a way to get to enjoy the boats we are building.”

Scarano’s first certified vessel was Madeleine, which was launched in 1992 by Classic Cruises of Newport. That company also operates the three-masted schooner Arabella that works the Caribbean, the Chesapeake and the New England coast; and Rumrunner, a true 1929 rumrunner “designed to do 50 miles per hour with 500 cases of booze aboard,” according to general manager John Taft.

Both Madeleine and Adirondack II are commissioned for 49 passengers and are operated by one captain/skipper and two deckhands who deftly maneuver their craft to dodge the dense traffic in the harbor and thread the needle past the often-congested docks of the wharves.

Above the waterline, these vessels look like traditional pilot schooners but they have no accommodations below and modern appendages under the hull, so both are a little bit faux (the masts of Adirondack II are carbon fiber disguised by wood veneer), but fast in light air.

Their regular schedule offers four to five sails that last from 90 minutes to two hours, and a sunset cruise, which typically is the most popular trip of the day.

Guests include absolute novices and folks who have tried their hand at tillers and sheets before. “We come here every year and Adirondack II is a fixture of our visits,” says Tracy Goldstein, who hails from Romsey, N.J. Goldstein is not a sailor, but her partner, John Puig, says he used to sail dinghies on New England’s lakes.

Paul Kosempel and his son William, from Denver, were peering over the schooner’s windward rail to spot jellyfish. “We’re visiting family in town and would rather go out on a sailboat than on one of the harbor cruisers,” says the older Kosempel, who grew up sailing Sunfish in Pennsylvania.

The third boat operating from Bowen’s Wharf, the 46-foot aluminum-built Sightsailer, designed by noted naval architect Yves-Marie Tanton, is distinctly different from the schooners. Originally the boat was meant to operate on Lake Pontchartrain near New Orleans, a notorious light-air venue. Compared to the schooners, Sightsailer is intimate, with room for only 16 passengers, but it’s probably the most exciting single-hulled charter boat to sail — easy to maneuver and fast.

Sightsailing, the operating company, also offers two O’Day 34 cruising boats for private charters and extended trips around Narragansett Bay. Owner John Hirschler, who sometimes subs as captain, is an old hand at the charter business in Newport, having started with a small Pearson Ensign. Later, he ran a Cal 34 before Tanton suggested he acquire Sightsailer.

“Sailing in a gentle breeze, taking in the sights of Newport, enjoying the bay, how can anyone possibly not have a good time?” Hirschler asks rhetorically. He estimates that all his boats combined take out about 12,000 passengers between May and October.

When Hirschler calls on his guests for a turn at Sightsailer’s wheel, Cathy Weber from Ohio is quick to respond. She spent three days in town with her family while her daughter attended basketball camp at UConn and loved the experience. “I’ve never sailed before, but this is wonderful,” she says. “One day, when I retire, I hope to own a sailboat.”

Farther north on Long Wharf, a little bit off the beaten path, but close to the Visitor’s Center, Flyer, a custom-built 57-foot catamaran designed by Walter Green is awaiting the multihull crowd. It’s owned and operated by Rhode Island natives Bruce and Dimity Reiss. This boat is licensed for 65 passengers and has a full-sized bar on the aft bridgedeck. The vessel spends summers in Newport and leaves for Florida in the fall where it’s available for charters and snorkeling trips.

Watching Bruce Reiss at the helm is highly entertaining. In his raspy voice he narrates over the intercom and commands the crew. While scanning his surroundings and adjusting the mainsail trim, he puffs on a cigarillo and exults as Flyer comes up on Castle Hill Lighthouse at double-digit speeds.

“I worked on boats, I worked in yards, I worked on cruise ships, I delivered boats to the Caribbean, and circumnavigated the eastern U.S.,” Reiss says, acknowledging a fixation with boats, and especially catamarans. “But when I got a ride from St. Maarten to St. Barths on El Tigre, the Spronk-designed cat, I was hooked on two hulls.”

John and Carol Kirkpatrick from Cumberland, R.I., have taken trips on Flyer before, but this time they brought their three children, daughter Julia and twins Evan and Ryan, all clad in life jackets.

“A cat is more stable than a normal boat,” John remarks, “I think it’s safer for the kids.” Sitting on the foredeck, enjoying wind and salty spray on their faces, Barbara and Jeffrey Alexander, two non-sailors from Hebron, Conn., confess to a different agenda. “We’re enjoying a getaway from the kids,” Barbara laughs. “We wanted to experience a catamaran; it’s fabulous.”

Right across the water on Goat Island is the dock of Aurora, the most classic and traditional-looking charter vessel with tanbark sails and a massive green hull. At 101 feet of sparred length, it is the largest of the Newport charter sailboats, licensed for 75 passengers. For more than 40 years, Aurora didn’t have a sailing rig, working in Maine from 1947 until 1991 as a fishing vessel that could haul up to 100 tons of herring in her two cavernous holds.

Only in 1991 was she converted to a passenger-carrying schooner and brought to Newport in 1996. Under the command of Ron Du’Prey, who like Aurora, hails from Maine, the schooner is available for charters, special events, and educational trips. Tuesdays at 10 a.m. Newport County residents can board Aurora for a free sail, while on Wednesdays and Sundays the schooner leaves the dock at 5 p.m. for a lobster boil and sail.

“Aurora operates differently from the other tour boats in Newport,” Du’Prey says. “We don’t do multiple scheduled sails a day so we have only one crew that consists of a captain, a mate and deckhands.”

Du’Prey has been at the schooner’s helm for five years, after spending significant time at the Museum of Yachting working on the exquisite restoration of Halloween, a famous 1926 cutter designed by Fife.

Rounding out the options for charter sailing on Narragansett Bay are the 12 Meter yachts, the remnants of Newport’s glamorous America’s Cup days. Three companies (Classic 12 Meter Charters, America’s Cup Charters and Seascope America’s Cup Adventures) are vying for customers. Prices are significantly higher than on the other boats (approximately $75 person or $850 per boat for a two-hour sail), but guests can expect the hands-on experience of sailing a classic racing yacht. The 12 Meters are popular for team building, upscale private charters, or as props for advertising photo shoots. Late in the summer, these boats enter classic yacht regattas to carry on a rivalry that dates back many years.

Next time your travels take you to Newport and you are not coming on your own keel, check out the daysailing boats to see the town from water. Add a sunset and a cocktail to the views and you have yourself a slice of paradise.

If you go:

Operators accommodate private charters with a variety of catering options, depending on the guests’ preferences. Calling ahead to make arrangements is recommended, even for a scheduled sail. This is especially true on holiday weekends or during the Jazz Festival.

Most of the seating on the boats is in open air, so bring sunscreen, cap, sunglasses, sneakers and a windbreaker.

12 Meter Charters, (401) 851-1216,

Adirondack Sailing Excursions, (401) 847-0000 (daysails), (401) 862-8441 (charters),

America’s Cup Charters, (401) 849-5868, (800) 820-1223,

Aurora, (401) 846-3022, (401) 841-0999,

Flyer (401) 848-2100, (800) 863-5937,

Madeleine (401) 847-0298,

Newport Sailing Tours, (401) 848-2266,

Seascope America’s Cup Adventures, (401) 847-5007,

Sightsailer, (401) 849-3333, (800) 709-7245,

History and sights

Dissidents seeking religious freedom, notably a separation of church and state, came to this area in 1639, making Newport one of the oldest settlements in the United States.

It’s location at the southern tip of Aquidneck Island and its sheltered harbor made it a center of shipbuilding, commerce and naval installations.

The temperate climate and the reliable, mellow summer sea breezes attracted members of New York’s high society, who followed Mrs. William Astor to Newport in the 18th century to build what they called “summer cottages.” As a drive down Bellevue Avenue or a stroll on Cliff Walk proves, cottage is a crass understatement for these mansions.

Some historic highlights the captains of the charter boats might point out during the sail:

After 1930, Newport was the chosen venue of the New York Yacht Club’s America’s Cup defenses, until the Australians wrested it away from Dennis Conner in 1983. The sailing tours pass Harbor Court, today’s summer residence of the New York Yacht Club that originally was the summer home of John Nicholas Brown.

Newport also was the wedding site of John F. Kennedy and Jacqueline Bouvier. South of town, past the fortress of Fort Adams, Hammersmith Farm sits on the gently sloped shore. The property served JFK as the Summer White House.

Fort Adams, once the largest coastal fortification in the U.S., now is part of a state park. It’s the venue of the Newport Jazz Festival and home to the Museum of Yachting.

Across the water, off the rocky shore of Jamestown, the boats sail past the Clingstone House, a large chalet on the rocks. It’s a rugged, not especially pretty structure that was built in 1902 for Lovering Wharton, whose original summerhouse was condemned to make way for Fort Whetherill. It withstood the hurricane of 1938 and was later restored. Many sailors (including some famous ones) learned a hard lesson in the thin water surrounding Clingstone.