Boston, MA

The Boston area coastline has so much to offer. From Martha’s Vineyard to Gloucester, coastal Massachusetts is a world renowned mecca for boaters of all kinds. Here are a few of our favorites just to give you a taste of what this area has to offer.



Lovells Island

A great swimming spot, Lovells Island, is sought after for its privacy. Of course, privacy also means no supervision, so be smart when swimming (especially on the ocean side). The ferry comes in and out during the summer. If you take your own boat you’ll have to anchor off shore, which shouldn’t be a problem since you’re going swimming anyway!

Harbor Islands

Boston Harbor is home to a National Park comprised of 34 islands and peninsulas. This is probably the best thing about boating in Boston. All but three islands are open to the public and many are only reachable by private boat. Many of the islands islands, such as Lovell, Peddocks and Grape, are great for overnight camping. You can drop anchor, find a secluded beach, and spend the day far from the traffic and crowds. Stop off at Bumkin Island to see the historic ruins or sail past Fort Warren on Georges Island, or visit Boston Harbor Light, the oldest lighthouse in the US. Not to mention the Harbor Islands are a premiere spot for sport fishing. Anglers here catch Stripers, Cod, Bluefish, and Flounder.

The Charles River

As long as you don’t have particularly large boat the Charles River is a blast to explore and a great place to see some of Boston’s history from a new perspective. You can go from the sights of downtown Boston (where there is free dockage along the river) and only just three miles up river it feels so remote you can believe there’s a city behind you. It’s worth seeing even for the experience of getting into the Charles from the harbor. You enter through the Charles River Dam and proceed through the historic locks (make sure you have a working horn to signal the locks to open). If you have a trailered boat you can launch at the Little Mystic Channel in Charlestown for quick access to the river.

World's End

In Hingham, about 10 nautical miles from Boston Harbor, is World’s End. On the east side of the island, through a little channel, you'll find a beautiful protected cove. This is a phenomenal place to barbecue, sunbath and spend the day in the gorgeous shallows protected by the peninsula of Nantasket Beach. It can be a quite a busy place on a weekends too; you’ll see all sorts of types spending a day afloat. Be sure to dock up at the Sea Dog Brew Pub in Hull on your way down or back for a drink and a bite. It's a fun spot overlooking the marina. The dockhands will make a reservation for you via radio after helping you tie up.


Cuttyhunk, the south western most part of the Elizabeth Islands, feels like the remote corner of Massachusetts that it is. The harbor in Cuttyhunk Pond is protected by sandbars that make for amazing beaches. In the summer the Harbor Raw Bar Boat will deliver oysters, clams, shrimp, chowder, and other delicacies right to your boat in the harbor, pond and marina from 5:15-7:30 pm. To order use channel 72 or go to the Fish dock. This destination dates back to the 17th century as a big game fishing mecca, but it’s now equally attractive for sailors and weekend cruisers. Although the harbor can, at times, be crowded, the island is really known as a quite, beautiful, and isolated spot to do some serious relaxation.

Cape Cod

The Cape has a spectacular number of places to explore. We love Chatham, located out on the south eastern reach of the peninsula. Whether you’re launching a fishing boat from Stage Harbor or sailing in from away, this place will knock your socks off. There’s the flat calm waters of the harbor and the Mill pond, then out past the lighthouse you havr great breeze for sailing. Local fishing here is fantastic, and stretches of white sandy beaches will keep you coming back. We also love Hadley Harbor, widely known as one of the best protected and most beautiful places to anchor in the area. It’s a stunning place to spend and afternoon picnicking and swimming or for an overnight. The surrounding islands are all beautiful, and you can spot the Forbes Mansion nearby!

Georges Island

A jumping-off point for some of the other islands, Georges Island, is home of Fort Warren, a Civil War fort with majestic archways that makes for a scenic walk. The island has a visitor center, ranger tours, gift shop and a place to eat. There are approximately 25 moorings available on a first come first serve basis.


Waterfront dining is not as prominent as you’d think in the city of Boston, so the few that accommodate “dock and dine” services are worth stopping by. Barking Crab in South Boston on the Fort Point Channel is a local seafood shack. If you’re docking at the restaurant it is recommended to call ahead (docks are first come, first serve). Also, your boat needs to be able to clear the North Avenue bridge, which is seven feet high. Don’t forget to watch the tide changes or you’ll be stuck at Barking Crab for longer than expected… but is that really a bad thing?

“The City on the Hill”

Boston is home to the Boston Harbor, an important port in any American history book because it was the location of the Boston Tea Party in the 17th century. Today, while much of the history of the Boston Harbor is still intact, so are many other amenities that tourists from around the country seek to find in Beantown and hitting the water on Boston boat rentals is a visitor’s dream.

Whale Watching

The Gerry E. Studds Stellwagen Bank National Marine Sanctuary is part of the Massachusetts Bay and a prime location for whale watching. It is common to see humpback, fin, minke, northern right and pilot whale, as well as Atlantic white-sided dolphin. Spring and summer are the best times for whale watching. Take your boat out to the bank and keep your fingers crossed for a “whale show.”


The best swimming in East Boston is at Constitution Beach. There are lifeguards and picnic areas and admission is free. For a more private experience, we recommend Lovells Island.

Boston Summertime

As is with many places that have harsh winters, Boston comes alive in the summer and the surrounding bodies of water become an important part of the culture and daily lives of Bostonians and visitors. If you’re not yet planning a summer vacation to the area, you will be – trust us.

Spectacle Island

Less than five miles from downtown Boston is Spectacle Island, a 114-acre island ideal for Boston boat rentals. The island offers panoramic views of the harbor and skyline. There is a marina on the island that allows you to ride over, dock up and spend the day checking out the evolution of the island. After you dock be on the lookout for the green visitor signs for information about all the island amenities.

Bumpkin Island

If long strolls on the beach sounds like your ideal Saturday afternoon then move Bumpkin Island to the top of your must-see list. A quiet camping destination, the island offers trials of wildflowers and shell beaches that make for the perfect afternoon walk. If you’re bringing your own boat, there are about 25 moorings available on a first come first serve basis.