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.