Written by Missy Johnston

Newport, Rhode Island
Photo Credit Missy Johnston

Join your charter yacht in Newport, RI at noon. Unwind, unpack and sip a cocktail as you depart the City by the Sea, into the beautiful waters of Narragansett Bay. Cruise to the charming village of Watch Hill. Nestled along the shore of Block Island Sound in the southwest corner of Rhode Island, Watch Hill is on a peninsula that is nearly surrounded by ocean. Stroll around this seasonal resort community to shop in quaint shops and view the beautiful cottages. Enjoy fresh, local lobster for your first dinner aboard.

Old Mystic Seaport, Historic Drugstore
Photo Credit Missy Johnston

It’s a short cruise up the Connecticut River to historic Mystic Seaport, one of New England’s most popular attractions. In and around this meticulous recreation of a 19th-century seaport community, you can watch craftspeople at work, go aboard the Charles W. Morgan, the last remaining wooden whaling ship, and view the many traditional wooden yachts based there. At Mystic Aquarium & Institute for Exploration, you can discover how modern-day explorer Dr. Robert Ballard discovered the Titanic while the “Challenge of the Deep” exhibit takes you on a `voyage’ 3,000 feet below the surface of the ocean. If dockage is available, dock right inside Old Mystic Seaport for the unique experience of being in the historic area in the evening to explore at will, after the living museum closes.

Audubon Center Hiking Trail

Spend the day leisurely cruising down Long Island Sound to Greenwich, Connecticut to dock and overnight. While many that live in this enclave work in New York City, this is one of the wealthiest villages in Connecticut. Perhaps check out the chic boutiques and shops. There are miles of trails to hike at the Audubon Center, and the Putnam Cottage welcomes visitors, as does the Greenwich Historical Society located in the Bush-Holley House Museum both built in the early 1700’s.

New York City Harbor and the Statue of Liberty

After breakfast, depart for Manhattan cruising down the East River, past the Upper East Side, and into the Harbor. While cruising enjoy the famous skyline and the Statue of Liberty. Dock in Chelsea Piers, located in lower Manhattan, and spend some time shopping and sightseeing or perhaps enjoying the theatre.

Sleepy Hollow, Tarrytown

Depart Chelsea Piers for a short trip up the Hudson River to Tarrytown, better known as “Sleepy Hollow”. Explore Sunnyside, the home of Washington Irving, and the village, the location of many of his stories. Also plan to visit Lyndhurst, the National Trust property of Jay Gould. Overnight. If reservations are made at least 3 month in advance, if there is availability, perhaps enjoy dinner in one of the restaurants at the Culinary Institute of America.

Manhattan Skyline at Night

Return to Chelsea Piers in New York City to enjoy all that this great city has to offer.

Port Jefferson Marina

In the morning cruise up the East River to the picturesque village of Port Jefferson. Spend some time browsing through chic and upscale boutiques, antique stores and art galleries. In the evening enjoy jazz, offered in several of the bars and restaurants.

Sag Harbor Village at Dusk

Depart after breakfast for a cruise to Sag Harbor, a quiet retreat of wooded hills, solitary beaches and exclusive vacation homes reachable only by sea. Originally named Wegwagonock by the Algonquin Indians, the first white settlers arrived in 1730 and renamed the area Sag Harbor. It quickly became a busy whaling port with a 31-boat whaling fleet in its’ heyday and now is a summer resort town filled with shops and boutiques to explore along Main Street, the Sag Harbor Whaling and Historical Museum, and several lovely restaurants.

Block Island Great Salt Pond

Just 12 miles off the coast of Rhode Island is Block Island, a seven-mile long by three-mile wide quiet island. Within the 25 square miles there are 17 miles of pristine beaches and a varied terrain of hills, hundreds of freshwater ponds, 2000 miles of stone walls and a unique variety of flora and fauna. Originally occupied by the Manisses Indians, it was named after Dutch navigator Adrian Block, who stumbled across it in 1614, then settled by a party of English from the mainland in 1661. Their struggle to subsist is reflected in the community today – in the ancient stone walls, in the old cottages, and in the farmsteads and mansard-roofed resorts. After lunch, explore the island by bike as there are several bike rental areas near the harbor.

Edgartown Harbor
Photo Credit Missy Johnston

In the morning depart for Edgartown, Martha’s Vineyard, an elegant port that takes itself and its yachting seriously. Many impressive yachts, belonging to the rich and famous, are moored here in season. As the “Vineyard’s” oldest and wealthiest town, Edgartown is equally impressive ashore. Go for a stroll down the cobblestone streets or walk the beaches of the famous Chappaquiddick point. Have lunch ashore at a dockside bistro and then take a tour of the rest of the island or head back to the yacht for some water sport fun or just relax on deck. Enjoy dinner on board.

Nantucket Harbor
Photo Credit Missy Johnston

It’s a short sail to Nantucket, aptly named by Native Americans, which means “land far out to sea”. For a quarter of a century whaling dominated almost every aspect of Nantucket life and was the sole basis of island wealth. Today, Nantucket’s wealth comes from fashionable summer residents, itinerant yachtsmen, an army of tourists and the seasonal scallop and cranberry industries. After dropping anchor, prepare for another day of water sports, sightseeing or just plain relaxation and pampering. After lunch on board take a tour of the whaling museum and the cranberry bogs. Then walk down the historical cobblestone streets or take a Jet Ski ride to the far reaches of the inner harbor.

Cuttyhunk Island Harbor

After a relaxing breakfast leave for Cuttyhunk and The Elizabeth Islands, the bottom of the chain of islands below Cape Cod. Enjoy lunch in Cuttyhunk Harbor before taking a hike to the islands highest point, which is a “must see” for a spectacular view of the eastward-running archipelago, its surrounding waters and the distinctive cliffs of Martha’s Vineyard to the southeast. If hiking isn’t your thing, swim or relax with cocktails as the sun sets.

Sailing into Newport

Return to Newport in the morning. There are several “must do” things in Newport, “the city by the sea.” The mansions are on the top of the list. These were merely summer cottages for the rich and famous following the Civil War. The Preservation Society of Newport maintains eight of the perhaps dozen that remain. One of the best ways to appreciate the sheer beauty of the mansions and their view of the ocean is by walking the Cliff Walk, a three-and-one-half-mile coastal path that hugs the coastline. Though it begins near First Beach (just off Memorial Boulevard) and ends on a side street off Bellevue Avenue, you can pick it up at several places along the walk, including Forty Steps, located at the end of Narragansett Ave. Beautiful at any time, early mornings are particularly magical, especially when the wild roses are in bloom. Other places to visit include the International Tennis Hall of Fame, the Museum of Yachting, the many galleries and “Antique Alley”, which is a cluster of antique shops grouped on Spring and Thames Street.

Newport Mansions

Disembark in Newport, Rhode Island