10 Things To Do Alone In Boston, Massachusetts - Updated 2022

things to do alone in Boston

Boston is one of America’s oldest, largest and most liveable cities, and each of these factors makes it a place worth holidaying in. It also features a wide range of accommodations, from Airbnb houseboats to hotels with rooftop bars. It’s a city you can truly get lost in, and have the most fun imaginable, thanks to its rich sport and food culture. Whether you want to experience Boston’s thriving Irish-American scene, take in a ballgame — the city has teams in the NFL, NHL, NBA, MLB and Major League Soccer — or experience one of the countless other options, it is right here for you. If you are a tourist who likes to travel in your own company, then you will be amazed by the wonderful tours that we have handpicked for solo travelers below. Read on to find out more!

1. Boston Hop-On Hop-Off Trolley Tour (from USD 50.0)

This thrilling experience takes you around the best places to visit in Boston, and offers you the chance to choose which ones you want to experience. Driving around Boston on a one-hour-and-45-minute loop, you can take the time to see the Tea Party Ships, the USS Constitution, and the bar that inspired the TV show Cheers, complete with the famous exterior. Stick to the timetable and you can pick the sights you want to see most - or you can stay on the bus a little longer and enjoy a serene progress around picturesque Boston!

Boston Hop-On Hop-Off Trolley Tour with 15 Stops

Duration: 1 hour 45 minutes

2180 reviews

2. Boston Ghosts and Gravestones Tour (from USD 46.0)

Swapping sightseeing for “frightseeing”, in the words of the organizers, this is a tour that will stand out for anyone with a love of the macabre. Among the high points, you will have the chance to see the final resting place of Cotton Mather, whose writings are felt to have been the greatest inspiration for the Salem Witch Trials. You will travel on the Trolley of the Doomed between two of Boston’s oldest burial sites, see the graves of prominent figures such as Paul Revere and Samuel Adams, and learn a little more about Jane Toppan and Albert “Boston Strangler” di Salvo, two of Boston’s most noted serial killers.

Boston Ghosts & Gravestones Night-Time Trolley Tour

Duration: 2 hours

639 reviews

3. Harvard: 70-minute "Hahvahd" Tour (from USD 19.5)

things to do alone in boston | harvard: 70-minute "hahvahd" tour

One of the world’s most noted universities, Harvard is an Ivy League school based in Cambridge, Massachusetts, and has a campus filled with history and magnificent red-brick buildings. The tour, lasting 70 minutes, will be led by a current Harvard student, making it an irreverent, funny look at this seat of learning through the eyes of someone who has made it their home. You won’t just have a few laughs, you are sure to learn a lot too. Perhaps not as much as the students themselves, but everyone will get something from the experience.

Harvard: 70-Minute Harvard Tour

Duration: 70 minute

894 reviews

4. Boston Freedom Trail to Copley Square Walking Tour (from USD 45.0)

You will need your walking shoes for this historic two-hour tour of numerous sites of Revolutionary War significance; rest assured, it will be worth the effort. There are numerous stops along the way on this morning hike that include Faneuil Hall, the Old State House, and the site on King Street, which is recognized as the place where the Boston Massacre unfolded. This latter occurrence was a major flashpoint in the war, and all the high and low moments of the city’s history will be brought to life by a knowledgeable and charismatic guide. You will see much of modern Boston too, including John Hancock Tower and other skyscrapers.

Walking Tour: Downtown Freedom Trail plus Beacon Hill to Copley Square/Back Bay

Duration: 2 hours

274 reviews

5. Boston Brewery Tour plus Lunch or Dinner (from USD 115.0)

This guided tour of the breweries of Boston is one that has proven very popular with visitors of the city. Visitors have the chance to sample up to eighteen different beers, from lager to stout and all points in between. Fortunately, round-trip transport is laid on! So, too, is food, with lunch or dinner being part of the tour depending on whether you take the early or late version. The tour is strongly recommended, with the guides showing an excellent sense of humor, as well as a powerful knowledge of the brewing process.

Boston Guided Brewery Tour with Tastings, plus Lunch or Dinner

Duration: 5 hours

210 reviews

6. Tour of Historic Fenway Park (from USD 33.0)

The home of one of America’s most-loved baseball teams, the Boston Red Sox, Fenway Park is one of the most immediately recognizable sports grounds in all of North America. It is also one of the things Boston is famous for. From the stadium’s roof deck, you can look out over the famous playing field and see the most famous fence in all of baseball, the 11-meter (36-feet) Green Monster. A trip around the Fenway Park Living Museum will be fascinating for any sports fan and may inspire you to come back and watch a match, or even sample a famous Fenway Frank hotdog if you visit between April and September.

Tour of Historic Fenway Park, America's Most Beloved Ballpark

Duration: 1 hour

850 reviews

7. Boston Whale Watching Cruise (from USD 71.0)

The aquatic wildlife off the coast of New England is majestic, and must be seen in the appropriate way to do it justice. On this whale watching tour of Boston’s coastline, you will get to travel in a high-speed catamaran and catch a glimpse of the most magnificent whales. However, these three-hour tours at the Stellwagen Bank National Marine Sanctuary allow you to get up close with not just whales, but also white-sided dolphins and porpoises. If you’re struggling to keep your sea legs, then retreat indoors to a climate-controlled indoor cabin where food and drinks are served!

Boston Whale Watching Cruise on a High-Speed Catamaran

Duration: 3 hours 30 minutes

1374 reviews

8. "Boston in One Day" Sightseeing Tour (from USD 89.0)

Of course, you can’t truly experience all of Boston in a single day - the city is 48 square miles (124 square kilometers) in size, so you are always going to run out of time. However, this tour condenses it all down into the essential Boston, and is a wonderful way to get to know the city. You can see the stunning suburbs of Lexington, Cambridge, and Concord, or shop in the Faneuil Hall marketplace, one of the city’s best shopping spots. You can also hear a bit about the history of the American Revolutionary War. You will do it all from the comfort of an air-conditioned coach and see all of the most beautiful scenery this remarkable city has to offer.

Boston in One Day Sightseeing Tour, with Lexington and Concord

Duration: 8 hours

795 reviews

9. American History Tour: Cambridge, Lexington and Concord Day Trip from Boston (from USD 66.0)

The neighboring towns of Cambridge, Lexington, and Concord are of huge importance to American history, and it was through these three famous neighborhoods that Paul Revere made his midnight ride in April 1775 to warn the colonial militia about the approach of British military forces. On this tour, you will follow the path he trekked, and witness historic landmarks such as Lexington Battle Green and Harvard Yard. You will also get to see the preserved old houses of pivotal Boston authors such as Ralph Waldo Emerson and Louisa May Alcott, who lived in the area.

U.S. History Tour from Boston: Cambridge, Lexington, Concord

Duration: 5 hours

304 reviews

10. New England Aquarium (from USD 32.0)

Staying with an aquatic wildlife theme, this indoor experience allows you to witness a more diverse range of creatures and witness IMAX movies that show you underwater creatures in the most amazing light. In the four-story Giant Ocean tank, you will see rare species such as tropical fishes, sharks, and a 550-pound (250-kilogram) sea turtle by the name of Myrtle. The aquarium is also home to a penguin exhibit, one of the most touching and exhilarating experiences you will have on your trip.

New England Aquarium Admission in Boston

Duration: 2 hours

10 reviews

You can take on Boston alone - and you may enjoy it even more!

Traveling on your own means you can go at your own pace and choose your own itinerary. That makes the experience of getting to know Boston all the more worthwhile, with attractions as wide and varied as aquarium tours and brewery trips. Don’t forget to check out the best dinner cruises and hiking spots while you’re here. Whenever you go, one thing is for sure - you will not run out of fascinating things to do in Boston!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Antonia Kelly is a freelance writer based in Leicester, UK and she enjoys European travel as well as road trips closer to home. Her favourite domestic destinations include Snowdonia and the Brecon...Read more

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