The ideal way to explore New England in the summer is by boat. You can explore beautiful harbors and towns yet escape the crowds that often flock to these areas during the warmer months. Escape the crowds and heat whenever you feel like it by setting off for an isolated anchorage, where you can live in peace.
Must See New England Places
There are hundreds of towns and harbors to choose from, but for a start, here are a few must-see ports of call that exude what New England summers are all about.
Newport, Rhode Island
The world-famous yachting destination. Some know her as the city that hosted the America’s Cup, while others know her as a protected harbor with plenty of nightlife and delicious provisioning. Newport is a great jumping-off point for cruising to Block Island, the Elizabeth Islands, Martha’s Vineyard, and Nantucket. All these places are just a day’s sail away, and depending on the point of wind, you can make sure that the sail (or motor) is comfortable for everyone on board.
Newport is a great city to walk around and take in the history of the place. From the Loeb Visitor Center, where you can learn about the day-to-day living of one of the older Jewish communities in the U.S., to watch the sunset over Newport harbor at The Lobster Bar, there is plenty to do and see for all ages. And, of course, there are the Newport Mansions. Rosecliff and Marble House are definite must-sees, while the Cliff Walk is a great way to exercise and take in the mansions on one side and the surf on the other.
Great Salt Pond is the main harbor here and is fully protected on all sides. It is pretty shallow in parts, so caution and a good guide are necessary if navigating this on your own. There are moorings, slips, and a 75-acre anchorage available. Ashore, visiting The Oar and Payne’s Dock is a must. There is nothing that tastes of summer quite like a rum punch while sitting outside, looking out at the harbor.
Although it is a bit of a trek, you can walk into town. Another option is taxis, generally standing along the docks, which is a quick and painless ride into town. There, you will find quaint shops, a couple of decent places to eat and drink, and the famous (or infamous, depending on who you talk to) Ballard’s, which serves food, drinks, and plenty of sights to behold. Many people come over for the day on the ferries from Montauk, New London, Newport, Point Judith, and Fall River and party it up on the beachfront of Ballard’s.
There are beaches in every direction on the island, so if you want to surf, kayak, or have a tranquil swim, there are plenty of options.
Cuttyhunk Island, The Elisabeth Islands, MA
You will shift gears on the New England coast when you anchor off Cuttyhunk. With a year-round population of around 50 people, this island provides a nearly 360-degree protected harbor with tons of beachfront. The Elisabeth islands offer miles of protected waters to explore, whether by dinghy or sail/motorboat.
There isn’t any nightlife in Cuttyhunk, but the town is fun and easy to walk around. You can always pop into the Cuttyhunk Historical Society to learn about the island’s unique history dating back to the 1600s when Bartholomew Gosnold first visited.
Vineyard Haven and Oak Bluffs, Martha’s Vineyard
Vineyard Haven has a lovely, protected harbor to pull into on your way around the island. The Black Dog Tavern is a great restaurant, offering brunch, wine tastings, and weekday dinner specials. The Gannon & Benjamin Marine Railway is a cool boatyard to check out, and it is world-famous for classic boat building and restoration.
Oak Bluffs is just around the corner from Vineyard Haven and is an easy drive or boat trip. Steamship Authority ferries arriving from Woods Hole regularly enter and exit both Vineyard Haven and Oak Bluffs, so be sure to stay vigilant when crossing their routes.
Oak Bluffs is famous for its cute Gingerbread cottages, similar in style and coloring to those found on Caribbean islands. Martha’s Vineyard has a rich African American history, and Oak Bluffs was once a vacation mecca for African Americans during racial segregation. The African American Heritage Trail of Martha’s Vineyard offers tours of the island and of Oak Bluffs, which provide insight into this history.
The Flying Horses Carousel in Oak Bluffs is one of the country’s oldest functioning carousels and is not to be missed if you have children in tow. You can rent the whole carousel for birthday parties during April, May, September, and October (after regular carousel hours). Make sure to try and grab the brass ring as you go around!
Edgartown, Martha’s Vineyard
Edgartown is larger than Oak Bluffs and Vineyard Haven, with many more restaurants and shops. It is a great place to rent a bike and spin around the nearby beaches, including Katama and South Beach.
There are moorings available in the harbor as well as an anchorage. This place can get filled up quickly in the summer, especially on the weekends.
No one can talk about cruising the New England coast without making mention of Nantucket. There are moorings, and anchoring is also allowed in certain areas, and there is, of course, dockage available too.
The island is ideal for biking around, considering how flat it is. Sankaty Head, Great Point, and Brand Point Lighthouses are great, and there are also plenty of beaches like Madaket and Dionis.
The Company of the Cauldron is a fantastic restaurant. The French-trained Chef Joseph Keller has worked in some of the best restaurants in the country. The cuisine is primarily American in taste but with French nuances. Make sure to make a reservation! CRU is also a great restaurant located right on the wharf front. Oysters and all other seafood are a must-try here.