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Lighthouses, Vineyards and Flying Horses

Greenport, N.Y.

Greenport, N.Y., is a bustling destination on scenic PeconicBay near Long Island’s wine country. You won’t find the glitz and glamour of an upscale seaside resort, but rather a small-town ambiance with much to offer visiting boaters.

Located on the south side of Long Island’s north fork, the Village of Greenport is about eight nautical miles west of Plum Gut. Approaching from the east you’ll pass the historic “Bug Light” at Long Beach Point. The lighthouse was fully restored in 1990, and its framework makes it looks like a large bug from a distance. Cruising farther west along PeconicBay, Greenport appears ahead to starboard.

Greenport is a traditional seafaring town that was first settled around 1640 and grew into an important whaling center in the 1800s. Menhaden and oyster fishing replaced the waning whaling industry in the early 1900s, and the town emerged as a summer vacation destination following World War II, after the decline of the once-thriving shipbuilding trade. The Long Island Railroad was extended to Greenport to support the whaling, shipbuilding and fishing industries, and now provides transportation for tourists.

The town continues to be revitalized, as many of the old captain’s homes on the tree-lined streets have been restored, with some converted to shops, restaurants or bed-and-breakfast inns. In recent years, waterfront facilities have been expanded in ongoing support of tourism. Mitchell Park was constructed with transient docks, a harbor walk and an amphitheater. The centerpiece of the park is a modern glass building housing a 1920s antique carousel. The East EndSeaportMuseum in the old train station near the ShelterIsland ferry dock provides information on the history of the town and features a collection of Fresnel lenses. Each fall the Maritime Festival celebrates the town’s seafaring heritage.

Greenport has an abundance of quaint gift, clothing and antique shops. Noteworthy is Preston’s Chandlery, which has been in business since 1880 selling marine supplies, nautical gifts and clothing. Located at the end of Main Street on the waterfront, it also offers transient dockage, but on weekends it tends to be choppy from boat traffic. You can relax on a bench behind the store and watch the dock activity. For a unique nautical shopping experience visit Triangle Sea Sales on the corner of First and South streets. Be sure to peruse Shipwreck Alley behind the store for used marine parts and treasures. For a touch of nostalgia, shop at the Arcade Department Store on Front Street, an old-fashioned department store complete with wooden floors.

There are many dining options in Greenport. Claudio’s has been in operation since 1870 and claims to be the oldest same-family-run restaurant in the United States, with locations on the waterfront and on Main Street. Dockage is available for waterfront diners. The Coronet Luncheonette, a village landmark, is on the corner of Front Street and Main, offering all-day breakfast and lunch in an old fashioned counter-style setting. Bruce’s Cheese Emporium on Main Street is a great place for a light breakfast, and for Mexican fare, try Meson Ole restaurant on Third Street. The Rhumb Line on Front Street offers a full seafood menu, and the Chowder Pot Pub near the ShelterIsland ferry dock has indoor and outdoor seating and live music. Bay & Main Restaurant & Lounge set back from Main Street offers food, drink and live music. The Village Cinemas on Front Street feature four theaters just across the street from an ice cream parlor.

Greenport is close to Long Island’s wine country and its wineries and vineyards. There are tours of the operations and tastings, as well as wine and gift shops and beautiful views of the vineyards stretching to the horizon. Check out the Long Island Wine Country Web site at for more information. To reach the vineyards contact Vintage Tours at (631) 765-4689. It offers air-conditioned van tours of some of the north fork wineries, with pickups at local marinas.

In addition to the in-town docking options, there are two harbors close to downtown Greenport. The harbors themselves are wonderful places to visit. Approaching from the east, calm and secluded StirlingHarbor is about half a nautical mile before Greenport. You will pass a breakwater and make a starboard turn to the marked entrance channel. There is no room to anchor, but transient moorings both inside and outside the harbor entrance are available from the harbormaster. There is a town dinghy dock on the west side of the harbor, and from there it is a short walk to town.

Also on the west side of Stirling Harbor is Townsend’s Manor Inn and Marina, with slips, hotel rooms, a pool and the Colonial Dining Room bar and restaurant. Brewer Yacht Yards has two marinas on StirlingHarbor and offers courtesy transportation to town. Enjoy a dinghy ride gunkholing through the scenic harbor. When the wind is blowing hard out in PeconicBay you won’t even feel it in well-protected StirlingHarbor.

Less than a mile across PeconicBay, to the southeast, is DeringHarbor on tranquil ShelterIsland. Dering Harbor isn’t as sheltered as Stirling, but it is a quieter alternative to downtown Greenport. UseShelterIsland as your base and take the short ferry ride over to Greenport. Dockage and moorings are available at Picozzi’s Dering Harbor Marina, while Jack’s Marine offers moorings and a marine store. ShelterIsland’s hilly and wooded shores are dotted with large summer estates overlooking the harbor and PeconicBay. If time allows once you’ve explored Greenport, take a bike or boat ride to see more of picturesque ShelterIsland.

There is much to see and do in the Greenport area: You can spend a day or an entire week’s vacation enjoying the town’s many amenities, the surrounding harbors and the nearby Long Island north fork wine country.

Montauk, N.Y.

Although Montauk is recognized as a fishing Mecca, it also is a terrific cruising destination. Entering the harbor between the breakwaters and transiting the channel, you will pass marinas with full amenities that offer transient dockage. Gosman’s restaurant and shopping complex is near the harbor entrance. As you pass Montauk Yacht Club the channel shoals in places to about 5-1/2 feet at low tide, so deep-draft sailboats may have to wait for a rising tide to ensure safe passage.

Farther along, the channel empties into LakeMontauk with depths throughout of about 8 feet at low tide. Even in peak season, you’ll find plenty of room to anchor. Most boats anchor in the southern end of the lake near the town beach, where you can land your dinghy. From here it’s almost a mile walk across land to the Atlantic beaches, where most days you will find surfers riding the waves.

Another mile and a half west by way of the beach or the road is the Village of Montauk. This oceanfront village has a distinct New York City flavor, as is evident in the many restaurants, bars, shops and bakeries. Ride a bike or take a cab out to the Montauk Point Lighthouse and museum. The view from the eastern tip of Long Island is just one more reason this is a great summer destination.

Watch Hill, R.I.

Watch Hill is a popular weekend destination for many boaters, as it’s an easy cruise from most places along Connecticut’s southeastern shore into Little Narragansett Bay. The large anchorage on the bay side of Napatree Point offers protection from the prevailing summer southwesterlies, and the bayside beach is a great place for children to enjoy the normally placid waters. Keep in mind that all of Rhode Island is a no-discharge zone.

Just a short hike over the dunes brings you to the ocean beach, which is favored for long walks out to the end of Napatree Point. On a clear day you can see all the way to Block Island, some 15 nautical miles away, from the tip of the point. Town is a short walk from the beach or a quick dinghy ride to the inner harbor.

Watch Hill has many interesting shops and a few eateries. The St. Clair Annex on Bay Street is a favorite place for ice cream as you walk around and enjoy this seaside village. Watch Hill also is home to the Flying Horse Carousel, considered to be the oldest operating merry-go-round in the United States. Watch the children’s faces beam as they ride the antique horses and try to grab the brass ring for a free pass to ride again. A short distance from town is the scenic Watch Hill Lighthouse, providing a magnificent view of Block Island Sound. This summer take a trip to Watch Hill and enjoy all that it has to offer.

Mattituck, N.Y.

Mattituck Harbor, on the north side of Long Island’s north fork, is a protected anchorage near a pretty town with plenty of amenities for cruisers. Breakwaters 18 nautical miles west of Orient Point mark the hard-to-see entrance from Long Island Sound. The winding and sometimes narrow two-mile-long Mattituck Creek may have 5-foot depths at mean low water in some places. At low tide herons and egrets feed along the marshes and mud flats.

The channel dead-ends at Matt-A-Mar Marina and the protected anchorage. Matt-A-Mar offers transient dockage and an on-site restaurant, A Touch of Venice. Near the anchorage is a small park with a dinghy dock, restrooms and showers. Mattituck’s tree-lined downtown area is only a half-mile walk from the dinghy dock, just past the train station.

A hardware store, gift shops and gourmet food shops specializing in coffee, ice cream, cheese and chocolate can all be found within one block on Love Lane. Good pizza can be found at Village Pizza nearby on Main Street, and farther on are movie theaters and grocery and drug stores. A short bike or cab ride takes you to nearby wineries such as Macari Vineyards, Lieb Cellars and Martha Clara Vineyards for tastings. After indulging on the wine and treats in town enjoy a nap back on board in the small, sheltered harbor.

Threemile Harbor, East Hampton, N.Y.

On peak summer weekends when many other harbors are full of boats, you can find plenty of room to anchor in scenic and tranquil Threemile Harbor. Part of the charm of this destination is getting there, as you cross Gardiner’s Bay with a view of pristine Gardiner’s Island. The breakwaters and beaches on both sides of Threemile Harbor’s entrance channel are lined with sunbathers and anglers enjoying the parade of boats on summer afternoons. Dinghy back later for a swim in the bay at Sammy’s Beach.

As you continue along the channel, shoreside homes, marinas and a few restaurants are nestled in picturesque marshes and woods. Eventually the channel widens into a protected lake-like harbor. Check your charts to be sure you are past the sandy shoal before turning into the anchorage. A quiet spot in the anchorage is the perfect place to read a book, jump overboard for a swim or gunkhole along the wooded shores.

If you tire of the solitude, dinghy to the head of the harbor and walk, catch a cab or ride a bus three miles into the center of East Hampton. The town is home to the rich and famous and includes upscale shops, restaurants and movie theaters. With the exception of a mid-July fireworks event when the harbor is packed with boats, this destination offers both quiet relaxation on the water as well as the hustle and bustle of town.

West Harbor, Fishers Island, N.Y.

West Harbor is a little jewel on Fishers Island, with pristine waters and rocky shores reminiscent of Maine. There are transient moorings available for rent in the inner harbor and a large anchorage in the outer harbor. Many visitors never leave their boats, however, content to relax and savor the harbor’s scenic surroundings.

If you do go ashore, Fishers Island is a great place for a long, leisurely walk, as the roads have little traffic and life seems to move at a slower pace. A walk on the road along the harbor on the northwest side of the island affords gorgeous views of Fishers Island Sound and the Connecticut shoreline. The eastern two-thirds of the island is scattered with large summer estates accessible by a single private road protected by a gatehouse.

The island has a military history, and many of Fort Wright’s buildings can still be seen near the passenger ferry landing at Silver Eel Cove on the west end of the island. The Henry L. Ferguson Museum, which moved into its new building in 2003, houses an interesting collection of birds, as well as island artifacts and relics.

A great way to end your time ashore is to visit Toppers, a fun little ice cream shop with a canine theme to all the treats. Memories of even a brief escape to this relaxing destination won’t soon be forgotten.

Stonington, Conn.

Located on Fisher’s Island Sound in the southeast corner of Connecticut, Stonington offers something for everyone. Historic sights, antique shops, gourmet restaurants and gorgeous views of the surrounding waters are all within a mile walk of the harbor.

A stroll through Stonington Village is reminiscent of a bygone era, as the streets are lined with restored Greek Revival, Federal and Colonial style homes. You can visit the Stonington Lighthouse and Museum on Water Street for the history of the village. Water Street runs the length of the borough and offers antique shops, cafes and restaurants. Noah’s Restaurant and the Water Street Cafe are just a few of the local favorites. Skipper’s Dock Restaurant has a long pier for docking while you dine, and provides excellent sunset views.

The south end of Water Street terminates at a waterfront parking lot and a small public beach. From here, there are wonderful views of Fisher’s Island Sound and Latimer’s Lighthouse. Stonington celebrates its heritage as a Portuguese fishing village with a traditional blessing of the fleet each summer for the fishing trawlers berthed in the harbor. It’s also a popular sailing town, with many sailboats moored inside the harbor breakwaters. Transient docks and moorings may be rented from Dodson Boatyard in the northeast corner of the harbor. This destination in the protected waters of Fisher’s Island Sound is an excellent alternative on days when seas are rough outside.

Lisa Brooks and Tom Schlagel are a liveaboard couple from Mystic, Conn., who seasonally cruise south and north on the Intracoastal Waterway aboard their Lagoon 380 catamaran, Symmetry.