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.

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  1. - Estimated Mileage: 0

    Safe Harbor Capri

    Overhead Review of Marina - Safe Harbor Capri - Port Washington, New York - Marinalife

    Port Washington, NY

    516-883-7800

    HIGHLIGHTS

    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.

  2. - Estimated Mileage: 35

    Danfords Hotel & Marina

    Danfords Hotel & Marina - Port Jefferson, NY - Marinalife

    Port Jefferson, NY

    631-928-5200 ext.123

    HIGHLIGHTS

    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.

  3. - Estimated Mileage: 38

    Mitchell Park Marina

    Mitchell Park Marina - Greenport, NY - Marinalife

    Greenport, NY

    631-477-2200 ext 1

    HIGHLIGHTS

    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.

  4. - Estimated Mileage: 8

    Sag Harbor Yacht Club

    Sag Harbor, NY

    631-725-0567

    HIGHLIGHTS

    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.

  5. Montauk, NY

    631-668-3100

    HIGHLIGHTS

    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.

  6. - Estimated Mileage: 20

    Champlin’s Marina & Resort

    Champlin's Marina & Resort - Block Island, Rhode Island - Marinalife

    Block Island, RI

    401-466-7777

    HIGHLIGHTS

    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.

  7. - Estimated Mileage: 23

    Safe Harbor Mystic

    Safe Harbor Mystic - Safe Harbor Mystic - Mystic, Connecticut - Marinalife

    Mystic, CT

    860-536-2293

    HIGHLIGHTS

    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.

  8. - Estimated Mileage: 20

    Saybrook Point Marina, Inn & Spa

    Old Saybrook, CT

    860-395-3080

    HIGHLIGHTS

    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 affords 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. 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. If you are in town during the last weekend of July, be sure to visit the 51st Annual Arts & Crafts Festival, which features more than 150 artists and crafters. And every Wednesday at 7 p.m. throughout the summer, Main Street hosts Concerts on the Green, a series of live music. Fresh Salt restaurant offers locally inspired dishes and handcrafted cocktails. Liv's Oyter Bay is a favorite for locals for seafood dishes, Penny Lane Pub is an English-style pub with live entertainment.

  9. - Estimated Mileage: 5

    Safe Harbor Dauntless Shipyard

    Boats Docked at Marina - Safe Harbor Dauntless Shipyard - Essex, California - Marinalife

    Essex, CT

    860-767-0001

    HIGHLIGHTS

    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.

  10. - Estimated Mileage: 63

    Safe Harbor Yacht Haven

    Safe Harbor Yacht Haven - Safe Harbor Yacht Haven - Stamford, Connecticut - Marinalife

    Stamford, CT

    203-359-4500

    HIGHLIGHTS

    The rejuvenated downtown of Stamford 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.The 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. Head downtown for local eateries including Sign of the Whale, a rooftop bar and grill and Teff restaurant, serving up authentic ethnic cuisine. If you're looking for old-school Italian meal head to Pellicci's, serving family-style meals for decades.