Cruising Itinerary: Montauk, NY, to Nantucket, MA

With a rich blend of history, culture and natural beauty, the New England coastline boasts an array of must-see boater destinations. Starting from Montauk, the easternmost point of Long Island, cruise to popular destinations in New England.

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Starting Point: Montauk, NY

This quintessential beach town stretches across miles of coastline lined with vintage boutiques and exquisite cuisine. Montauk, or “The End” as locals call it, has morphed from fisherman’s enclave to a polished surf town.

WHERE TO DOCK

Safe Harbor Montauk Yacht Club

This marina offers transient slips for vessels up to 300 feet with complimentary pump-out and Wi-Fi, on-site dining and lodging at the luxury seaside resort.

WHAT TO DO

Montauk is a popular saltwater fishing spot for anglers to try their luck reeling in species like striped bass, tuna and fluke. Also known as a surfing destination, head to Ditch Plains Beach for surf breaks or take a lesson from a local surf school. Witness majestic gentle giants on whale-watching tours or visit the historic Montauk Point Lighthouse for breathtaking views of the Atlantic Ocean.

Restaurant Recommendations: 668 The Gig Shack, Navy Beach Restaurant, The Lobster Roll, Harvest on Fort Pond, Muse @ the End

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Leg 1: Montauk to Block Island, RI

Estimated Mileage: 17 NM

Block Island seems to have it all — art galleries, hiking, fishing, bars and shopping, all within arm’s reach. Bike scenic trails across the island or visit cafés and inns near Water Street in Old Harbor. If you’re in search of oysters, steamers or lobster, you can’t go wrong with the local restaurants.

WHERE TO DOCK

Champlin’s Marina & Resort

This resort marina in New Shoreham offers 4,500-plus linear feet of dock space, fuel, and charming guest rooms and cottages.

WHAT TO DO

Block Island is known for sandy shorelines such as Crescent, Ballard’s and Mansion beaches. Swing by the Waterfront Sports Area conveniently situated at the Dinghy Dock and enjoy complimentary paddleboards, kayaks, or pedal boats. The island serves as a sanctuary for birdwatchers, boasting over 100 species. Old Harbor features quaint shops, art galleries and restaurants.

Restaurant Recommendations: Kimberly’s, The Beachead, Poor People’s Pub, Dead Eye Dick’s, The Mohegan Restaurant & Bar

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Leg 2: Block Island to Newport, RI

Estimated Mileage: 24 NM

Newport is the site of world-class events, seafood, tennis, polo and more. Walk the gorgeous 3.5 mile Cliff Walk that traces the edge of the sea and visit famous historic mansions of the Gilded Age like the Marble House. Check out the International Tennis Hall of Fame Museum and the grass courts and do not miss the scenic Ocean Drive.

WHERE TO DOCK

Newport Yachting Center

Dockage for vessels up to 180 feet is available right in the heart of town at the Newport Yachting Center, as well as amenities including fuel, boat maintenance, shower facilities and free Wi-Fi.

WHAT TO DO

Hit the historic waterfront during September for the Newport International Boat Show and walk the docks to see a stunning display of new sailboats and powerboats, browse marine products and accessories, attend educational seminars and more. Cruise Narragansett Bay and pass by the iconic lighthouse or indulge in Newport’s fine dining. Check out Easton’s Beach for surfing, King Park Beach for sunbathing and Fort Adams State Beach for swimming.

Restaurant Recommendations: Midtown Oyster Bar, Portside by 22 Bowens, Wharf Southern Kitchen, Pasta Beach, Diego’s, Giusto, and Bar ‘Cino

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Leg 3: Newport to Cuttyhunk, MA

Estimated Mileage: 25 NM

On the way from Newport to Martha’s Vineyard, stop at Cuttyhunk Island, the fourth-largest area of the Elizabeth Islands and home to a charming village within the town of Gosnold. Rather than lively pubs, this destination is famous for its quiet, isolated environment and activities such as fishing or relaxing by the water.

WHERE TO DOCK

Cuttyhunk Marina

Located between Buzzards Bay and Martha’s Vineyard, this 50-slip marina accommodates vessels up to 100 feet and offers 50 town rental moorings.

WHAT TO DO

Spend a tranquil day on one of the three main beaches: Church’s, Barges or Channel, or embark on a fishing journey across the bay. The sandy shores are ideal for beachcombing sea glass and hidden treasures. To learn about history and culture, head to the local museum at the Cuttyhunk Historical Society.

Restaurant Recommendations: Cuttyhunk Picnic Co., Cuttyhunk Shellfish Farms, Cuttyhunk Island Market

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Leg 4: Cuttyhunk to Martha’s Vineyard, MA

Estimated Mileage: 15 NM

Martha’s Vineyard is known for its history, fabulous shops, delightful pubs and Atlantic shoreline breezes. Learn about rich history and culture through exhibits, artifacts and interactive displays at the Martha’s Vineyard Museum.

WHERE TO DOCK

Vineyard Haven Marina

This facility provides deep-water moorings and dockage accommodating vessels up to 200 feet, plus staff will arrange shoreside accommodations such as dining reservations, island tours and transportation.

WHAT TO DO

Martha’s Vineyard has beautiful beaches including Moshup Beach in Aquinnah, Wasque Point, on Chappaquiddick Island. Standing since 1817, visit the historic East Chop Lighthouses for picturesque views. Shop the town’s unique boutiques, art galleries and restaurants or experience live theater, workshops and events like “Monday Nights at the Movies” at Martha’s Vineyard Playhouse.

Restaurant Recommendations: Garde East, Beach Road, Salvatore’s, The Black Dog Tavern

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Leg 5: Martha’s Vineyard to Nantucket, MA

Estimated Mileage: 25 NM

Nantucket is noted for its dune-backed beaches and stunning shingled buildings. Steepled churches, designer boutiques and phenomenal eateries line the cobblestone streets and old wharves. Attractions include the Nantucket Whaling Museum, the Old Mill and Sankaty Head Lighthouse.

WHERE TO DOCK

Nantucket Boat Basin

This pet-friendly facility accommodates boats up to 200 feet and offers lodging in charming cottages, plus fuel dock service, slip-side cable TV and complimentary pump-out, as well as 18 baths and showers located throughout the site’s three wharves.

WHAT TO DO

Nantucket boasts more than 80 miles of pristine coastline with beaches including Children’s, Jetties, Surfside, Madaket, Dionis and Cisco. Grab a bicycle to cruise the island or rent a 4x4 SUV for an off-road adventure along 16 miles of sand roads and beach at Coskata-Coatue Wildlife Refuge. Enjoy shellfishing for mussels and blue claw crabs or join a whale-watching tour to see magnificent marine life in their natural habitat.

Restaurant Recommendations: Slip 14 and Bar Yoshi on Old South Wharf, Straight Wharf Restaurant, Cisco Brewers and Triple Eight Distillery at Nantucket Vineyard