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Beaches, golf courses, and fine wineries. One of Forbes’ Prettiest Towns in America, the village of Greenport, New York retains its maritime history while providing exquisite modern accommodations. Founded as an authentic whaling town, Greenport transformed into a hub of the fishing industry and later, the railroad industry. After a period of success as an oystering center, Greenport remains a favorite destination for tourists.
With the Peconic River as an eye-catching background, tour Greenport’s boutiques, museums, restaurants, and old-fashioned general stores. Visit the Railroad museum of Long Island and East End Seaport Maritime Museum to immerse yourself in Greenport’s revolutionary past. Fill your belly with oysters and barbecue from Moonlight Mondays at Corey Creek, and rock out to live music and tapas at Sparkling Pointe.
Home to Kurt Vonnegut, Joseph Heller, John Steinbeck, and Nora Ephron, among others who worked or lived nearby, Greenport New York has also retained its artistic heritage. Now art galleries participating in Greenport’s gallery walk remain open late on the first Friday of each month from June to December, providing visitors with the opportunity to stroll through the village and appreciate local artwork.
Welcome Aboard! We departed from our homeport in Vero Beach, Fla., headed north to Maine aboard our 78' Ocean Alexander, Rhythm 'n Blues. This journey took us to many ports of call, traveling over 5,500 nautical miles from Florida to Maine and back. The daunting task of making all of these marina reservations was made easy with the help from the Marinalife staff. The length of this cruise created a new rhythm for us which leads to the boat's name, Rhythm 'n Blues. Now hop aboard as we take you through our journey from the Chesapeake Bay to Maine.
This was one of the highlights of our trip. College friends who were married the same year as us joined us for our 35th anniversary cruise through the Chesapeake Bay. We made it our quest to find the best crab cakes on the bay. We began this leg of the trip at Bluewater Yachting Center in Hampton, Va., The surf rider restaurant was the first of our many crab cakes!The next day brought us to The Tides Inn in Irvington, Va., We biked to The Dog and Oyster Winery and had dinner and of course crab cakes at the Tides Inn Restaurant.
Zahniser's Yachting Center in Solomons Island, Md., was beautiful. We took the dinghy all around the island where the topography was so interesting with cliffs and lovely scenery. We enjoyed crab cakes at Stoney's Seafood House.
Oxford, Md., was one of our favorites places to explore! All of the quaint homes were in perfect condition. Many residents partner with local artists for a contest in which they paint a portion of the resident's white fence, better known as onion tops. We stayed at the Brewer Oxford Boat Yard & Marina and had crab cakes at Schooner's on the Creek.St. Michaels, Md., was another fun spot with lots of shops and restaurants. We docked at St. Michaels Marina, which was an easy walk to everything. We actually had two crab cake tastings: The Crab Claw Restaurant and St. Michaels Crab & Steakhouse.
Annapolis was bustling with energy! We stayed at Annapolis City Dock and we were in the thick of the action. it was fun exploring the Naval Academy and all of the shops and restaurants that align the streets. Steps away from the boat was the winning crab cake, located at Dock Street Bar & Grill!
We finished off the Chesapeake Bay with stops in Chestertown, Rock Hall and Georgetown before cruising through the C & D Canal toward Atlantic City, N.J. Then we made our way to the Big Apple for an extended stay.
New York City, or should I say the Big Apple, will rate up there as one of the most memorable days of our trip. Bringing the boat right up to the statue of Liberty was amazing. We wanted to sing God Bless America at the top of our lungs!
After a night at Danfords Hotel & Marina in Port Jefferson (locally known as Port Jeff), we traveled to Mitchell Park Marina in Greenport and on our way we passed Plum Island. For all of you Nelson DeMille fans (novelist) you will know exactly where we are. Mitchell Park Marina is located in town and we enjoyed a nice walk to Claudio's for dinner (a Greenport landmark the oldest family-owned restaurant in the United States since 1870). The next day we biked to Kontokosta Winery and did a wine tasting at this beautiful winery overlooking Long Island Sound. There are at least 50 vineyards in this region, and we have been surprised by the quality of the wines.
We left Greenport and had a short hour and a half ride to Sag Harbor, an upscale little town that is not far from the Hamptons with very nice shops and restaurants. We had lunch at Page Restaurant and enjoyed the very good grilled octopus!
Our final stop on Long Island was Montauk. Montauk Yacht Club is very nice with two pools, restaurants, a beach and a spa. After watching the sunset, we were greeted with a supermoon.
Newport, R.I. is a city steeped in history and architecture. We docked at Newport Harbor Hotel & Marina and toured two of the Summer Cottages as they are called. The Cliff Walk was a wonderful winding walk that follows the coastline for 3 1/2 miles. Seeing the cliffs and the water crashing onto the rocks was quite a thrill!
We were happy that we docked at The Black Dog Wharf because Martha's Vineyard has a nice historic streets with shops and a few restaurants.Nantucket, Mass., has wonderful walking and bike paths throughout the entire island. We loved seeing the residential area with the immaculately restored homes on the cobblestone streets. The yards are lush and manicured with an abundant amount of hydrangeas in every color imaginable! We docked at Nantucket Boat Basin.
In Boston, we stayed at Constitution Marina located on Boston Harbor conveniently situated on the Freedom Trail. Boston Commons is unique with the swan boats and Newbury Street, the historic high-end shopping district with lots of outdoor cafes. We took the dinghy down the Charles River. It was the first time we have ever done locks in a dinghy! From the water we saw Harvard, Boston University and MIT.
We left Boston and headed to Newburyport, Mass., a wonderful little town. Arriving during their big Yankee Homecoming Festival, the streets were lined with white tents and the park had concerts during the day and fireworks at night. We tied up at Newburyport Harbor Marina and had delightful dinner at Ceia Kitchen Bar a small European restaurant.
The next day we headed to Boothbay, Maine. On our way we saw a water spout and, wouldn't you know, it was a whale! To be so close to such a huge creature was awe inspiring! The scenery and temperatures changed quite a bit as we made our way into the harbor. It was absolutely beautiful!
You know you have entered Maine when you can walk across the water on lobster trap buoys. It requires major maneuvering skills to make your way through the waterways and harbors. We took the dinghy out the next day to the town of Bath. Again, another amazing day of beautiful scenery spotting seals on our journey. The dockmaster asked us where we had gone and when we told him Bath, he said, "You took that little dinghy through Hells Gate, that's adventurous!" (I guess that's what they call that section of 6-knot rapids that we had to go through!)
We were in Rockland, Maine for a few days. We were able to dinghy over to Rockport (not to be confused withRockland) and also to Owl's Head Point. Very beautiful coastal countryside. Lots of art galleries for visitors to explore in Rockland.
We finally arrived to Bar Harbor, Maine and met our daughter Stephanie and her husband John. They hiked Precipice which is the most difficult hike in all of Acadia National Park. My wife and I had already hiked Precipice 20 years ago so we had our bragging rights! The guidebook says climbers should expect an experience physically strenuous and mentally stimulating. We decided that might be too tiring. The next day we all hiked Acadia Mountain together, which the guidebook called moderately strenuous. Let's just say their definition of moderate is a little different from Kristi's!
The Atlantic Ocean flows to the west from Block Island Sound to create the estuary called Long Island Sound. Every year, this inland sea gives boaters a summer full of cruising opportunities. At the eastern end of Long Island Sound, where the set and drift of the strong currents of The Race and Plum Gut test one's navigation skills, is the Fishtail. Long Island is one hundred miles long (hence the name), and its eastern tip when viewed on a chart resembles the tail of a fish.
As a young boy growing up on the streets of Brooklyn, weekend trips to Mystic Seaport with my father instilled in me love of the sea and maritime history. Today, the Seaport still draws crowds with sea fever and a strong desire to learn about our country's maritime heritage.
Mystic Seaport (860-572-5391, mysticseaport.org) also has its own marina with transient docks, and admission to the museum is included in your dock fee. Brewer Yacht Yard at Mystic (860-536-2293, byy.com/Mystic) is also a great place to tie up offering a full service boat yard, onsite swimming pool, laundry and shower facilities.
Plan on an early start down the Mystic River to cross the narrow end of Long Island Sound. Enter the North Fork of the Fishtail at Plum Gut between Orient Point and Plum Island. Once in Gardiners Bay, cruise westward keeping Shelter Island to port. You will soon arrive at Greenport, your first stop after your 30 mile morning cruise. Spend the late morning and early afternoon ashore exploring the village of Greenport, which was named one of Forbes' Prettiest Towns in America.
Tie up your vessel right in town at Mitchell Park Marina (631-477-2200, villageofgreenport.org) and have lunch at Claudio's Clam Bar or Claudio's Crabby Jerry's along the town wharf.After a short siesta, fire up your engines and double back into Gardiners Bay. This time keep Shelter Island to starboard. Three Mile Harbor is your destination, 12 miles away on the south shore of the bay. Three Mile Harbor is a well protected body of water located three miles from East Hampton. Both Halsey's Marina and Gardiner's Marinas (631-324-5666, sea-incorp.com) offer 10% off dockage for Marinalife members throughout the summer.Just east of the harbor is the hamlet of Springs, whose name probably does not ring a bell.
However, the names of the Jackson Pollock, Willem de Kooning, Kurt Vonnegut, Joseph Heller, Phillip Roth, John Steinbeck and Nora Ephron may. These artists and writers have all worked or lived in nearby Springs. Although culturally important, Springs doesn't have the draw of East Hampton. Most boaters just take the short taxi ride into town to shop and to have dinner at one of the tony restaurants. Perhaps you'll spot David Geffen who just paid over $50 million for hisEast Hampton estate.
After staying up to the wee hours with the young and hip in the East Hampton night club scene, you are probablytempted to sleep in late, and have a latte delivered to your boat. Feel free to indulge, as your next port of call is Sag Harbor for lunch only 10 miles to the west. Most of Sag Harbor village is a national historic site which focuses on its prominence as a shipping and a whaling port from the 1790s to the 1860s. Enjoy a walking tour of the town after lunch, check with the tourist information center at the windmill at Long Wharf. Dock at Sag Harbor Yacht Club (631-725-0567, sagharboryc.com) just a short walk from town.
After departing Sag Harbor and rounding North Haven Peninsula, cruise southwesterly across Noyack Bay leaving the needle tip of Jessup Neck on your port side. Continue down Little Peconic Bay to Robins Island. Head north around the island through the North Race into Great Peconic Bay, and keep an eye out for shoals. Carry on across Great Peconic Bay, to Flanders Bay and continue up the Peconic River. This afternoon leg is about 25 miles, and you can tie up for the night at Treasure Cove Resort Marina (631-727-8386, treasurecoveresortmarina.com) in Riverhead offering Marinalife members 10% off transient dockage. The hamlet of Riverhead is the center of Long Island wine country and has almost 50 vineyards and wineries in the surrounding area (during the summer season the marina offers a daily shuttle service to local areas).
In the morning, cruise back out flanders Bay into Great Peconic Bay, round Red Cedar Point and continue eastward along the south shore of the bay for some gunkholing. In succession, explore the back waters of Red Creek Pond, Cold Spring Pond and Sebonac Creek and North Sea Harbor. If you have a stand up paddle board or sea kayak on board, drop your anchor and see what you can discover.Continue northeasterly to Shelter Island in the afternoon, and the entrance to West Neck Harbor off Shelter Island Sound. The harbor has a designated anchorage area at southern end, or call ahead for a slip for the night at The Island Boatyard & Marina (631-749-3333) at the northern end. Either have dinner and dessert at the nearby Island Cafe, or just relax on the hook after a great day of cruising, sipping a glass of Long Island pinot noir. This picturesque island has five harbors to explore, each with its own unique flavor. You will be tempted to stay for more than a day. Stop by Sunset Beach (631-749-2001, sunsetbeachli.com) and drop anchor and enjoy drinks at the lively beachside restaurant and bar.
Capt. Jeff Werner has been in the yachting industry for over 25 years. In addition to working as a captain on private and charter yachts, both sail and power, he is a certified instructor for the USCG, US Sailing, RYA and the MCA. He is also the Diesel Doctor, helping to keep your yacht's fuel in optimal condition for peak performance. For more information, call 239-246-6810, or visit MyDieselDoctor.com. All Marinalife members receive a 10% discount on purchases of equipment, products and supplies from Diesel Doctor.
Long Island Sound could busy mariners for years. Its glacially-sculpted namesake Long Island borders the south. Connecticut creates the northern shores. The Big Apple shines from the west. This 100-mile tidal estuary of the Atlantic Ocean carries boaters from working waterfronts to quiet coves and crannies, and everything in between.
To sample some of Long Island Sound's finest harbors, start at Stamford, Conn. You'll see growth everywhere as millennials move in to enjoy the economic progress and sophisticated spillover from nearby New York. The rejuvenated downtown is marked from Washington Boulevard to Grove Street with This is the Place! banners. Getting from waterfront to downtown is an easy hop on the Harbor Point Trolley loop at one of its 14 stops. A highlight is The Palace Theatre, originally a vaudeville house now featuring a wide selection of theatre, opera, dance and concerts. For a look at what is going on in the city, visit Stamford Downtown at www.stamford-downtown.com.
Brewer Yacht Haven Marina (203-359-4500, www.byy.com) is located on the East Branch of Stamford's Y-shaped harbor. This is the less commercial of the two branches, although new development for recreational boaters is radically changing the waterfront everywhere. The marina offers transient slips. On the way in, look for the 19th-century replica Schooner SoundWaters, the education vessel of a Stamford nonprofit that works to protect Long Island Sound.
Port Washington is at the head of Manhasset Bay, which is 15 nautical miles southwest of Stamford. You are heading toward New York, and these are active waters; locals long ago dubbed the bay Exit 1 on Long Island Sound. Three area yacht clubs Manhasset Bay, North Shore and Port Washington keep yachts racing year-round (frostbiting started here in the 1930s). Seaplanes land in restricted harbor areas.
Port Washington is a good home base for forays into New York, just a 45-minute train ride into midtown. The opulent area is where F. Scott Fitzgerald began writing The Great Gatsby and clearly got the inspiration for his allusions of wealth. Sands Point Preserve is on the original Guggenheim Estate, where there are tours of the Hempstead House, a sprawling castle that once served as a summer residence. It's one of four mansions on the grounds and a short bike or cab ride from Brewer Capri Marina (516-883-7800, www.byy.com), located to the east of Plum Point. The marina has East and West yards close together with most transients docked at the West yard, which is also where you can fuel up. Although reservations are recommended, these folks go out of their way to accommodate every request.
From the marina, dinghy to the town dock or hail the Port Washington Water Taxi, which will take you just about anywhere. The taxi also gives harbor tours. The village itself is replete with diverse restaurants. One longtime favorite is the landmark fish house Louie's Oyster Bar & Grille, a feisty dockside establishment that opened in 1905. La Parma is another well-regarded option for Italian food. For shopping that rivals Fifth Avenue, catch a cab to Americana Manhasset, a shopping area three miles south of town with designer brands and high-end restaurants.
Some 35 nautical miles to the east is Port Jefferson, commonly called Port Jeff. Chances are you will cross paths with a defining feature of the town, the ferry that runs hourly across the sound from Bridgeport, Conn. The Bridgeport & Port Jefferson Steamboat Company, whose first president was P.T. Barnum of circus fame, runs the 75-minute ferry ride as well as a plethora of additional touring options (1-888-44FERRY).
Port Jefferson was an active shipbuilding center in the mid-19th century. The Mather House Museum provides a glimpse into the home of some of these shipbuilders, while the Maritime Explorium at Harborfront Park is located in an 1890s chandlery and now features hands-on interactive family activities. Theater Three on Main Street entertains all ages. Check their website at theaterthree.com.
On any given summer day, downtown bustles with arrivals by boat, ferry, train, motorcycle and car. Restaurants, shops, galleries and markets are all within walking distance of the docks. There are farmers markets on Sundays, as well as free harborfront concerts, movies and children's shows throughout the summer (www.portjeff.com). The Port Jeff Brewing Company runs a tasting room and tours of the brewery (on Saturdays only). Fishing enthusiasts will be happy to know that catches are plentiful both inside the harbor and outside the jetties. In summer, you'll have a chance at fluke, bluefish and striped bass.
Danfords Hotel & Marina (631-928-5200, www.danfords.com) sits on Port Jeff's snug, deep-water harbor with excellent protection during rough weather. It is part of a luxurious retreat, steps from the village. At the marina, Admiral's Deck features dockside dining, while WAVE Seafood Kitchen serves indoors with a waterview.
At approximately 55 nautical miles, the cruise to Greenport is the longest leg of this journey. It requires rounding the north fork at Plum Gut to enter Gardiner's Bay and then following the channel north of Shelter Island. This may be the lesserpopulated end of Long Island, but it harbors loyal boaters, and lots of them, who come back season after season. Be sure to make reservations early for in-season transient dockage, and check cancellation policies.
Greenport is an excellent home base for exploring Long Island's North Fork, whether that means gunkholing in the Peconic Bay estuary or taking short ferry rides to Shelter Island and then on to Sag Harbor. There are pristine beaches, golf courses and wineries. Two Brewer facilities are on the east side of Stirling Basin Brewer Yacht Yard at Greenport (631-477-9594) and Brewer Stirling Harbor Marina (631-477-0828, www.byy.com). Both are full-service and provide complimentary shuttles to the village. Another outstanding option is the town's Mitchell Park Marina (631-477-2200,villageofgreenport.org) located right in town.
The historic seaport of Greenport is lined with boutiques, old-fashioned general stores, museums and restaurants of all varieties. An antique carousel gifted from the Grumman Aircraft Corporation 100 years ago makes daily rounds at Mitchell Park. You'll get a free ride if you snag the brass ring. The East End Seaport Maritime Museum at the ferry dock ushers visitors into the area's seafaring and shipbuilding past. It features a saltwater aquarium with flora and fauna from Peconic Bay and a working blacksmith on weekends at the Village Blacksmith Shop. The museum runs lighthouse cruises to the iconic Long Beach Bar Bug Light and creates a weekend-long maritime festival in September. Switch over to the heritage of the tracks at the nearby Railroad Museum of Long Island.
A visit here is not complete without a stop by two Greenport institutions Preston's Chandlery and Claudio's Restaurant. The former is a mariner's browsing treat, and the latter is about as hopping as a waterfront restaurant gets in summer. The music blares from afar on weekends. Try the Peconic Bay clams or oysters at Claudio's and people watch or enjoy those local oysters in a quieter atmosphere at The Frisky Oyster. For some highly-rated pizza and a speakeasy vibe, head to Brix & Rye on Main Street. It's just a taste of what cruising on Long Island Sound has to offer.