Family-Friendly Boat Outings in Boston, MA

Family-Friendly Boating Activities in Boston, MA

Written by Boatsetter Team
April 1, 2021

Last Updated on November 28, 2022 by Boatsetter Team

Boston Harbor is one of the oldest and most important in America. There’s no better way to see than from the deck of a boat. Exploring the bays, rivers, or inlets nearby is a great way to see Massachusetts’ capital city from a new angle. 

Boston is famous for many attractions, like Fenway Park or the Boston Marathon, for land-bound visitors. But the natural beauty visible from the city’s many waterways is perhaps one of the best and least talked about attractions. The estuary environment provides a home for various wildlife and creates a unique boating opportunity. 

Seeing Boston By Boat

The easiest way to explore Boston Harbor if you’re visiting or don’t own a boat is through a peer-to-peer app like Boatsetter, which lets users experience all the fun of sailing without the hassle of boat ownership. Using this P2P option also lets you choose from a variety of boat styles and the option to sail under the guidance of a local caption who can show you the best of Boston Harbor.

Planning a boat trip to Boston can be challenging if you’ve never been there before. Even native Bostonians have lots to discover out on the water. Check out some of the following ideas when you’re charting your adventure.

Best Boating Activities for Boston

  1. Cruise Through Downtown Boston

Spend the day sailing down the Charles River and get a view of some of the most iconic buildings in the city. The Esplanade should be on your list, alongside the MIT campus and the waterfront once you get into the harbor. 

The Charles stretches for 80 miles in total, so you can take your time enjoying the sights. Anglers can cast their lures for crappie, perch, catfish, carp, and the odd striped bass. Take a sport yacht like the C-Lark II and ask the captain to drop you off in the center of Boston to continue exploring on land when night falls. 

  1. Castle Island, Pleasure Bay, and Carson Beach

There are three places for newcomers to the Boston Harbor to go fishing, sunbathe, and swim very close to the city. Castle Island is home to Fort Independence, an old defensive structure that dates back to the 17th century. 

Further south, you’ll find Pleasure Bay and Carson Beach. Visit by boat to avoid crowds and ensure you have a swimming spot all to yourself. A 35 Sport Cuddy is the perfect cost-effective way to visit all three places and take in some sun and sightseeing all at once.

  1. Go Fishing In Quincy

Boston Harbor has tons of different targets for anglers of every skill level. Striped bass, scup, bluefish, tautog, weakfish, mackerel, bluefin and yellowfin tuna, bonito, cod, and more are available here. Chasing these targets out of Quincy allows you to explore the harbor islands and gt away from the fishing crowds. 

We recommend a 28-foot contender and plenty of plugs, flies, and live bait to haul in some fish. Sail to The Graves for great fishing and Boston’s tallest lighthouse or the Brewsters throughout the summer and catch a new personal best. 

  1. Set Sail for Nantasket Beach

Head out to the far end of Boston Harbor in style above a classic sailboat like a Custom Dubois to see as much of the harbor islands as possible and luxuriate in the sun while you do. Once you get there, you’ll have a wonderful view of a clear beach that you won’t believe is so close to one of the northeast’s biggest cities. 

Alternatively, you could explore Hingham Bay. There are plenty of parks around so you can get some great sightseeing in. Go in the summer for warm weather or try to catch the leaves changing in autumn. 

  1. Personal Lighthouse Tour

Boston is home to three important and stunning lighthouses. Boston Light is the first one in the country, while Graves Light and Long Island Light share the same northeastern maritime charm. You might be able to find lighthouse tours around the city, but if you want a luxurious voyage, try making your private tour onboardLuxury Motor Yacht

You can see the natural beauty of Boston Harbor while enjoying drinks, a meal, or swimming breaks on your schedule. If you’re going to sail around the harbor, there’s no better way to do it. It’s a unique boating destination that has much more to offer than you might be expecting. 


Browse by experience

Explore articles