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!
Why Trust Trip101?
✅ Over 50,000 articles reviewed and published by our experienced team
✅ Over 50 years of combined experience researching, writing and reviewing travel articles
✅ Over 40,000 hours spent on research and fact-checking from credible sources (last year’s data)
✅ Optimizing content from data-driven insights collected directly from users on our platform
✅ Focus on authentic and up-to-date information by collaborating with local guides, global travelers and other industry experts
✅ Long-standing partnerships with credible brands like Airbnb, Booking.com, Agoda, Expedia, GetYourGuide, Viator, RVShare and more
✅ Full disclosure on any partnerships or sponsored content
Trip101’s team of writers, editors, and content managers oversees the publication of all travel content, including destination guides, accommodation recommendations, and travel tips. They have extensive experience in the travel industry and no content, written or visual, gets published without a review. Many of our team’s work has also been featured in Travel+Leisure, National Today, The Indian Express, The Telegraph (India), Robb Report, The Adventure Handbook, Tripoto, Korea Tourism Organization, and Korean Ministry of Culture, Sports and Tourism. Some of them are also members of professional organizations like the Society of American Travel Writers and the International Travel Writers and Photographers Alliance.
Each member of the team follows Trip101's methodology and strict editorial guidelines to ensure accuracy, authenticity, and relevance.
1. Boston Hop-On Hop-Off Trolley Tour
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!
Book Tours : Boston Hop-On Hop-Off Trolley Tour with 14 Stops
2. Boston Ghosts and Gravestones Tour
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.
Book Tours : Boston Ghosts and Gravestones Trolley Tour
3. 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.
4. Boston Freedom Trail to Copley Square Walking Tour
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.
Boston Tour Guide
Naim Benmayor
As a Boston tour guide, I have the added experience of being a world traveler. For many years, I frequently visited Europe, Asia, and Latin America on business. During this time, I also organized tours of the USA, Europe and Asia for my business clients. I now bring this passion, excitement and expertise to the Boston area.By exploring the globe, I was exposed to various cultures, and this uniq... Read more
5. Boston Brewery Tour plus Lunch or Dinner
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.
6. Tour of Historic Fenway Park
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.
7. Boston Whale Watching Cruise
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!
Book Tours : Boston Whale Watching Cruise by High-Speed Catamaran
8. New England Aquarium
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.
Book Tours : New England Aquarium Admission Ticket in Boston
9. "Boston in One Day" Sightseeing Tour
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.
10. American History Tour: Cambridge, Lexington and Concord Day Trip from Boston
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.
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!
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
