Cruising Stories

Cruising Itinerary: Manhattan, NY, to Stamford, CT

New England
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By
Marinalife
City Island Avenue, City Island, Bronx NY - credit Andre Carrotflower/Wikimedia Commons
City Island Avenue, City Island, Bronx NY - credit Andre Carrotflower/Wikimedia Commons

Exploring the tri-state area is sure to keep mariners busy. Its glacially sculpted namesake — Long Island — borders the south, with Connecticut along the northern shores and the Big Apple shining from the west. This 100-mile tidal estuary of the Atlantic Ocean stuns boaters from working waterfronts to quiet coves and everything in between. Starting from New York City, embark on this journey along the East River into the Long Island Sound to Connecticut.

STARTING POINT: MANHATTAN, NY

Chelsea Piers Marina

Situated along the Hudson River in bustling Manhattan, this marina offers 65 slips for vessels up to 300 feet. Upscale amenities include access to the Fitness Club, two sundecks and indoor pool and it is walking distance to the High Line and Chelsea Market. What to Do NYC — aka the city that never sleeps — is a tourist capital that boasts endless activities just minutes from the water. However, boaters won’t need to venture far from the marina as Chelsea Piers offers various sports and entertainment venues such as rock climbing, ice skating, bowling, golfing, and field sports. Stroll along the Hudson River Park to explore urban green spaces and walk the High Line, a public park built on an elevated freight rail line on Manhattan’s West Side.

Restaurant Recommendations: Water Hazard Bar + Lounge (on-site at the marina), Bluestone Lane (at Pier 62), Salinas Restaurant, Bocca di Bacco.

Leg 1: Manhattan to City Island, NY

Estimated Mileage: 20-25 NM

City Island is a quaint sportfishing village in the Bronx offering the perfect laid-back escape from the busy city.

Where to Dock

South Minneford Yacht Club

This facility is located at the historic Minneford shipyard established in 1926 and offers both memberships and transient slips. Amenities include showers, gas grills, a picnic area and fish cleaning station.

What to Do

The city’s main street, Island Avenue, runs the entire length of the region with a shopping district, upscale dining and waterfront access. Book fishing charters through Jack’s Bait & Tackle or explore the city’s maritime heritage at City Island Nautical Museum.

Restaurant Recommendations: Sammy’s Fish Box, Johnny’s Reef, The Black Whale, The Original Crab Shanty

Sailboat passes by Execution Rocks Lighthouse on Long Island Sound - credit Getty Images
Sailboat passes by Execution Rocks Lighthouse on Long Island Sound - credit Getty Images

Leg 2: City Island to New Rochelle, NY

Estimated Mileage: 4 NM

Just 30 minutes from Manhattan, New Rochelle is the seventh largest city in New York boasting 9.3 miles of shoreline and 231 acres of public parks. Local neighborhoods showcase elegant, stately homes dating to the late 19th and early 20th centuries.

Where to Dock

New Rochelle Municipal Marina

Located only 20 minutes by train from NYC, the marina offers 350 boat slips, 150 moorings, kayak storage along with launching and hauling, winter boat storage, mobile and stationary marine pump-out services and it is walking distance to local entertainment and grocery stores.

What to Do

Take a stroll at Hudson Park & Beach or visit Glen Island Park for scenic views of Long Island Sound. Check out downtown’s Walk of Fame, play golf at the Wykagyl Country Club, attend a performance at the public library’s Ossie Davis Theater, or visit the Thomas Paine Cottage Museum, the former home of the famous political activist.

Restaurant Recommendations: Dubrovnik Restaurant, AJ’s Burgers, Alvin & Friends.

Leg 3: New Rochelle to Mamaroneck, NY

Estimated Mileage: 4 NM

Heading northeast along the sound, stop by the picturesque town of Mamaroneck, one of the oldest communities in Westchester County dating back to the 1600s. Originally occupied by indigenous Siwanoy Indians, the Native American name Mamaroneck translates into, “the place where the sweet waters fall into the sea.”

Where to Dock

Safe Harbor Post Road

Nestled in the protected east basin of Mamaroneck Harbor, this marina offers wet slips for vessels up to 60 feet. Amenities include a fuel dock, vessel service, boat storage and complimentary Wi-Fi.

What to Do

Head to the 44-acre Harbor Island Park to kayak or paddleboard the Long Island Sound or stroll the town’s charming shops, antique stores and attractions throughout two main villages. Nature enthusiasts can hike the Hommocks Conservation Area and explore trails along the Colonial Greenway.

Restaurant Recommendations: 25 North, Augustine’s Salumeria, Sal’s Pizzeria

Leg 4: Mamaroneck, NY, to Greenwich, CT

Estimated Mileage: 10 NM

Sailing north along the sound, crossing over the New York state line and witness the natural beauty of Connecticut’s coastline. The swanky town of Greenwich is known for its upscale amenities, fine dining, shopping, museums, and beautiful waterfront setting.

Where to Dock

Delamar Greenwich Harbor Marina

This stunning resort marina offers over 500 feet of private dockage for vessels up to 180 feet and top-notch guest services from full-time dock attendants. Enjoy resort amenities including the spa, fitness center and provisions.

What to Do

Explore world-class art, science and natural history at the Bruce Museum or the Bush-Holly House Museum. Visit Greenwich Point Park, a 147-acre town-owned park and beach known locally as Tod’s Point (formerly the estate of J. Kennedy Tod). Stroll Greenwich Avenue known by the locals as the Ave, and find a mix of boutiques and high-end dining.

Restaurant Recommendations: L’Escale Restaurant (on-site at the resort), Mediterraneo, Le Pain, Meli-Melo, Elm Street Oyster House

Stamford, CT - credit Denis Tangey Jr
Stamford, CT - credit Denis Tangey Jr

Leg 5: Greenwich to Stamford, CT

Estimated Mileage: 7 NM

Continuing north along the Connecticut coast, Stamford combines New England charm with a delightful mix of cultural, recreational and culinary experiences.

Where to Dock

Harbor Point North Marina

Just steps from the Harbor Point Boardwalk, this 34-slip marina accommodates boats up to 120 feet for seasonals and transients, plus access to top-tier amenities like watersport rentals, free water-taxi rides and the only fuel facility available in Stamford, the Fuel Dock at Hinkley Yacht Yard. Check out additional marinas at Harbor Point properties located throughout Stamford such as Harbor Point East and West.

What to Do

Enjoy a stroll through the beautiful Stamford Museum & Nature Center or catch a performance at the Palace Theatre. Head north to Mill River Park to enjoy outdoor sculptures and green spaces or east to Cove Island Park for walking trails, beaches and picnicking. Stamford’s downtown area boasts an impressive array of cafés and boutiques making it perfect for foodies and shoppers alike.

Restaurant Recommendations: Fortina, Sign of the Whale, MEXiCUE

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