Where to Enjoy the Cruising Life


Mystic Seaport in Connecticut make a great stop on a two or three day cruise.

So, you have your boat—excellent first step. Now, what to do with it? Make sure you’re prepared, know the rules of the sea and get out there!

But perhaps you’re stuck on where to go exactly. Luckily for you, Sag Harbor is the perfect launch point, with anywhere from half-day cruises to 2-week voyages within reach.

“This is a great place to live for boating,” longtime boatman Charlie Canavan said. “It’s better than anywhere I’ve seen in the world, where there’s so much to do without going too far. There are so many great locations for cruising.”

It is important to note that different boats travel at vastly different speeds, Jim Larocca said, so the following guide should be taken as just that. Know what is possible for your craft and adjust accordingly, he said.

And most of all, have fun!

A Half- or Full-Day Jaunt


If you’re craving a bit of culture, stop off for a visit to the Atlantis Aquarium, the Vail-Levitt Music Hall and the Suffolk Theater, Jim Larocca, an avid boater out of Sag Harbor, said. But for a meal or cocktail, Phil’s in Aquebogue, right near Lighthouse Marina, is the place to be, Mr. Canavan added.

Watch out for the fixed bridge in Riverhead, though, which has a limiting clearance of 25 feet. If you have a larger powerboat or sailboat, you’ll have to skip the docks and marinas here.

SALT on Shelter Island.

Shelter Island

This is a favorite among avid Sag Harbor boaters. West Harbor and Coecles Harbor are great anchorages for an afternoon of swimming and sunning aboard, Mr. Larocca said, and SALT restaurant comes highly recommended by Mr. Canavan. Head over to Dering Harbor for additional dining options and a walk around Shelter Island Heights, or the historic Chequit Inn for drinks, at least.

Shelter Island Yacht Club welcomes visiting day and overnight boats, Mr. Canavan noted.


Chockfull with history, lively dining, shops — especially antiques — and music on the docks, Greenport is a stellar day trip out of Sag Harbor, and a must for kids once they hop aboard the carousel.

Dock at Mitchel’s, Claudio’s or Barba Bianca and enjoy multiple stops in town, Mr. Canavan said. Orient By The Sea is a must for lunch or dinner, he said, as well as a convenient place to gas up.

Gardiner’s Island

Owned by the same family since 1635, this is a great place to anchor—preferably in the bay below the historic manor house, Mr. Larocca said—and soak up the historic vibe of the largest privately owned island in the United States.

A Little to the East, A Little to the West

To stay even more local, head east to Accabonac Harbor, Three Mile Harbor, Fort Pond Bay and Lake Montauk, or west to the Shinnecock Canal, which is a foodie’s haven — home to the Canal Café, Cowfish, Rhumba, Sunday’s and Oakland’s.

The Griswold Inn in Essex, Connecticut.

Take A Day, Or Three

Across the Long Island Sound

Head up the Connecticut River to Essex and the Griswold Inn, a very sociable gathering spot for boaters and landlubbers and nice walking about, though make sure you keep going a mile or so north of Essex to Hamburg Cove. It’s a must-see, Mr. Larocca said.

The Essex Yacht Club and neighboring marinas have accommodations for boats large and small, he said.

Fishers Island

This is one of those rare gems, accessible only by private boats and a ferry from Connecticut. Most of the island is private — very private — but West Harbor is accessible and the Fishers Island Yacht Club welcomes visiting boats, Mr. Larocca said. Walking around the west end is a great way to spend the day, he said, and Saturday nights at the Pequot Inn, which is the only saloon on the island, are memorable.

Noank, Mystic and Stonington, Connecticut, and Watch Hill, Rhode Island

These are all perfect for overnight stops, Mr. Larocca said.

Anchoring inside of Napatree Beach at Watch Hill is especially nice for swimming and walking, he said, and the historic Ocean House not far from there is gorgeous—and just a door or two beyond Taylor Swift’s (heavily guarded) summer house.

The Mystic Seaport is probably the most authentically restored village of its kind anywhere, Mr. Larocca noted, and check out Stonington for nice restaurants and beautiful homes. Dodson’s Shipyard offers the best moorings in the inner harbor and there is a huge anchorage in the outer harbor, he said.

Block Island

Prepare to see a lot of East Enders, as this is one of their favorite haunts. It’s a beautiful piece of real estate, Mr. Larocca said, with plenty of walking, bicycling, beaching and perambulating in town during the late afternoon and evening. Catch a film at the local movie theater and, the following morning, look out for a local family that sells bread and baked goods to all the boats moored in New Harbor.

The Newport lighthouse.

Newport, Rhode Island

You can spend a night, a week or a summer and love every minute in this very sociable city, Mr. Larocca said.

A sailing and boating mecca, the city is rich in history and architecture from colonial times through the golden age of mega-mansions, he said. Grab some great food and libations up and down Thames Street, and explore the city’s additional quarters. The city is home to the oldest synagogue in America and The Casino, an elegant grass-courted tennis venue from the late 19th century, and the Naval War College promises a big Navy presence, he said.

If nothing else, make sure you check out the Cliff Walk around Newport Neck, Mr. Larocca said. It’s a must.

The Perfect Trip for Three to Five Days

Cuttyhunk, Massachusetts

The southernmost of the mostly private Elizabeth Islands — running 14 miles from Cutty to Woods Hole in the north — Cuttyhunk has about 60 year-round residents, a small general store, an old fishing club where past U.S. presidents have hung out, a delightful little harbor and fabulous walking trails. It is also the site of an unsolved off-season murder dating back to 1984!

Most of the Elizabeth Islands are owned by the Forbes family, but boaters can stop at the beautiful Hadley Harbor — but not go ashore — or Tarpulin Cove, where you can go ashore to the old lighthouse site, but no farther.

Also, the oceanographic institute at Woods Hole welcomes visitors, but beware: it is a tricky harbor to get in and out of, and the tides and currents must be respected.

Take Five to Seven Days, Even Up to Two Weeks

Buzzards Bay and Cape Cod, Massachusetts

Make stops in New Bedford, Mattapoisett and Marion, or at the north end of Buzzards, boaters may choose to enter the Cape Cod Canal and head over to Cape Cod Bay.

There, you can see famous stops like the charming town of Wellfleet — which can be shallow and tricky, but well worth the effort — or Provincetown, which is a wide-open harbor with good depths, lots of moorings and easy access to the liveliest town on the Cape.

A couple days ashore in Cape Cod are probably a minimum for boaters who have journeyed all the way from Sag Harbor, Mr. Larocca said. Great ocean beaches are an easy walk from town, he said, and Provincetown is home to restaurants, music, clubs and possibly the latest nightlife anywhere on the Cape.

Downtown Provincetown, Massachusetts.

Martha’s Vineyard, Massachusetts

The alternative to the Cape Cod Canal and Provincetown is to slip out of Buzzards Bay at either Quicks Hole or Woods Hole, and into Vineyard Sound, Mr. Larocca said.

From there, you have your choice: the old fishing village of Menemsha, a beautiful and quiet place, or Vineyard Haven, a major ferry landing, as well as a real town, with a movie theater, the Vineyard Playhouse, the Black Dog Cafe and other fine restaurants. Transport is available to tour the island and sample the beaches and countryside.

Next north is Oak Bluffs, also a ferry stop, and a town with everything from an old summer prayer campground, to major “cottage” architecture given to bright Caribbean colors, to all kinds of shops, restaurants and arcades.

And finally, there is Edgartown — as well as Chappaquiddick Island, beyond — a pretty colonial town with beautiful architecture, especially the churches and public buildings. The south end of the bay opens to Katama, and some of the most unspoiled beaches in the northeast.

Nantucket, Massachusetts

Once the richest settlement of its kind in New England, and the whaling industry capital of the United States, Nantucket — with its cobblestone streets and brick mansions — simply captivates, its wonderful downtown on the harbor recently revitalized after undergoing major improvements in the last few decades.

It seems that half of the historic houses have become summer B&B’s, so if you’re looking for a night or two off the boat, you have your pick. But for the saltiest of visitors, the Jared Coffin Inn and the Club Car saloon downtown are legendary stops, Mr. Larocca said.

“This may seem obvious, but bear in mind that all trips require time to get home,” he added. “Here again, it depends on the boat, but it is fair to plan to take as long to get back to Sag Harbor as it took you to get to your furthest destination. Or, simply decide that the cruising life is for you and let the wind, weather and tide decide when it is time to be homeward bound.”

Share This!