Cruising the Long Island Sound

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. 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.

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. At the marina, Admiral’s Deck features dockside dining while WAVE Seafood Kitchen serves indoors with a waterview. 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 farm markets on Sundays as well as free harborfront concerts, movies and children’s shows throughout the summer.

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. A visit here is not complete without a stop by two Greenport institutions – Preston’s Chandlery and Claudio’s Restaurant. 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.

A historic whaling town, Sag Harbor prides itself on being “unHamptons.” The Sag Harbor Whaling & Historical Museum promotes the area’s rich culture. Foster Beach on Noyack Bay is a great place to unwind after a long day of fishing, clamming, or paddle-boarding in the harbor. Walking distance to town, there is an abundance of restaurants nearby, including the American Hotel, the Corner Bar, Dockside Bar & Grill, Nello Summertimes, and Cittanuova.

As a quintessential beach town, Montauk offers expansive beach access stretched across miles of coastline featuring vintage boutique shopping and exquisite surf cuisine at popular eateries such as The Gig Shack and The Hideway Restaurant. Montauk, or “The End” as locals call it as the easternmost part of Long Island, has morphed from fisherman’s enclave to a polished surf town. IGA Grocery is located about 3 miles away from Montauk Yacht Club.

Whatever you are searching for, Block Island seems to have it: art galleries, hiking, fishing, bars, food and shopping are all available within arm's reach, and you'll be no farther than a 20-minute bike ride from the southern and northernmost points of the Island. You'll find most of the island's cafés and inns near Water Street in Old Harbor. If you're in search of oysters, steamers or lobster, you almost can't go wrong with any of the local restaurants. Finn's Seafood Restaurant is a popular place for seafood, and its fish market below the restaurant emphasizes their commitment to getting you a fresh meal. Take-out is also available. The Salty Dog on Water Street is a local institution, and offers a wonderful view of Old Harbor. The Orange Cat Café offers a variety of baked goods and some excellent coffee. For those with a sweet tooth, look for Blocks of Fudge on Chapel Street.

There’s plenty to do, particularly for those cruising with kids. The waterside streets are lined with shops, galleries and restaurants, and there’s also a planetarium and children’s museum. No trip here is complete without a tour of Mystic Seaport, the nation’s leading maritime museum or the Mystic Aquarium & Institute for Exploration. The Capt. Daniel Packer Inn serves fine food in an atmosphere that's truly New England-especially the downstairs tavern. Two blocks away in the opposite direction look for Mystic Pizza, which inspired the movie of the same name, as well as many delis and pubs. Your crew will enjoy the continental menu at the Flood Tide Inn. Provisioning in Mystic is fairly easy with numerous markets among the downtown shops. A mile east of town, the A & P Super Foodmart.

Old Saybrook, 27 miles west of Mystic, sits where the Connecticut River meets the Long Island Sound. Saybrook Point was the site of a prominent fort and an important coastal trade center during the 1700s and 1800s for vessels from river boats to ocean ships. Present day Old Saybrook is as charming as ever, dotted with clapboard houses, boutiques, antique stores, galleries, and cafes that brim with history. The town’s coastal location a ords ample opportunity for water activities. To the southwest is Harvey’s Beach, a perfect spot for the entire family to cool off on a hot day. Kayakers will love exploring the North Cove and South Cove, both very protected. And there’s plenty of nonwater fun to be had too. In this bike-friendly town, cycle along the 10-mile loop out to Saybrook Point for breathtaking views, meandering along Long Island Sound as you go. Be sure to make a detour to check out Lynde Point Lighthouse, which sits at the mouth of Connecticut River. Ready for a game of golf ? Stop by the Fenwick Golf Course, completed in 1896, to play a round. The waterfront Mini-Golf at Saybrook Point will make everyone in the family happy.

Steps from the waterfront, Main Street is home to an eclectic array of boutiques, gift shops and stores, as well as several places to dine. Chief among these is the Griswold Inn, which has been serving mariners since 1776 and is the oldest continually operating tavern in the country. There’s plenty to do and see in and around Essex, starting with the excellent Connecticut River Museum, directly on the waterfront. The Essex area offers numerous marsh-lined creeks to explore in a kayak or SUP. On the opposite side of the river, you can enjoy the beach at Nott Island and explore this wildlife preserve. Places to dine locally include The Griswold Inn, a local institution known for its hearty food — featuring a pub and wine/tapas bar with live music and Abby's Place for casual breakfast. For casual seafood and pub fare on Main Street head to Black Seal Grille.

Brewer Yacht Haven Marina 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.