With historic sites, charming neighborhoods, beautiful public parks, a variety of museums, and delicious dining options, there are plenty of things to do in Boston. It is one of those cities I could repeatedly visit and experience differently each trip. But, what should you do on your first visit?
That is exactly what I tried to figure out during my first trip to Boston.
The Massachusetts capital had been on my travel wishlist for years. Finally, I visited in March 2015. Although I was there for Women in Travel Summit (WITS), I planned to make the most of my limited time in Beantown.
Was I successful? I think so. Yet I barely scratched the surface of all the attractions I’d like to visit in Boston. And the foods I want to eat.
Whether you like art, history, food, craft beer, sports, or films, you could easily build a Boston trip itinerary around your interests. If you are like me, you probably want to experience everything. While that is logically not possible in a long weekend trip, you can certainly make a dent in your list of things to do in Boston and get a real feel for the city within a few days.
So, if you are visiting Boston for the first time, I’ve got five ideas for how to quickly acquaint yourself with the city.
First Of All, Take A Tour Of Boston!
When I’m visiting a new destination, my favorite way to get to know the area is by taking a tour. Walking tours sometimes require using public transportation, which allows travelers to learn how to navigate the local subway or bus system.
Walking tours are also ideal for photo opportunities. If you enjoy photography or just coming home from your travels with photos of beautiful scenery, you should look into taking a PhotoWalks tour. PhotoWalks offers guided photography tours of the waterfront, Freedom Trail, Beacon Hill and Back Bay neighborhoods, and Boston Public Garden. I’d love to do this on my next visit. I’m just not sure how I’d choose which tour to take!
While I love walking tours, don’t discount bus tours — like the Boston Hop-on Hop-off Trolley. Bus tours tend cover a broader area, giving you an idea how the city is laid out. Both walking and bus tours are often full of insightful notions and fun facts that only the locals seem to know.
Sightseeing tours are best if you are interested in seeing all the city’s sights in a short time frame. Boston Duck Tours, which traverse the city by land and the Charles River, came highly recommended to me by one of my cab drivers and the Boston local I was seated next to on my flight from Detroit to Boston Logan International Airport. Since the vehicle drives right into the river, I’d say a Duck Tour would be one of the most fun things to do in Boston with kids.
Unique And Unusual Tours In Boston
Are you a history buff? A foodie? A literary geek? A film aficionado? Into ghost stories or pub crawls? Then skip the generic sightseeing tour! Opt instead for a tour tailored to your interests. I took two tours specific to my interests during my first couple days in Boston. After the tours, I was confident I could get myself around the city by foot or the T. I also pinpointed the landmarks, neighborhoods, and attractions I wanted to explore further on my own.
Here are a few tours that sound pretty awesome and are currently available to book on Viator:
- Boston Ghosts and Gravestones Tour — As you hear tales of “lost souls” believed to be haunting the streets of this historic city, you’ll walk through two of the oldest burial grounds in Boston, including the Old Granary, where Paul Revere, Samuel Adams, John Hancock, and the five victims of the Boston Massacre are buried. Book your tour now!
- Boston Movie Mile Walking Tour — See famous movie and TV locations around Beacon Hill and Boston Common on a 1.5-hour tour. You’ll have a drink at the Cheers bar, where everybody knows your name, and see the famous park bench from Good Will Hunting. Don’t miss out — reserve your tour today!
- North End Pizza Tour — Learn a bit of North End history as you taste three slices of pizza — including one from Boston’s oldest pizzeria! Reserve your slice(s) by booking your tour now!
Foodie Tours Around Boston
My first tour — “Bittersweet Boston” — was offered to WITS 2015 attendees and was led by a Boston local. With our local guide leading us, our group rode the T to the end of the green line and walked with umbrellas in hand through the pouring rain to the Taza Chocolate factory and Bantam Cider.
The last stop was The Independent. It’s a local pub with an excellent selection of craft beers and deliciously potent cocktails. Several ladies on my tour liked the Man Moth, a mix of bourbon, Averna, cinnamon, honey and whiskey-barrel-aged bitters.
Although the Bittersweet Boston tour was a one-time event, you can find a number of other foodie tours in and around Boston.
Boston Movie & TV Location Tours
The second tour I took was a Boston TV & Movie Sites Tour with On Location Tours. Our bus tour took us past settings used in Good Will Hunting, The Departed, Ted, Field of Dreams, Mystic River, and The Town among many other movies. I hadn’t even realized how many films took place in Boston!
Eat At One Of Boston’s Oldest Restaurants
Boston is full of restaurants serving delicious dishes, but none have done that longer than America’s oldest restaurant — Union Oyster House, established in 1826. Jacob Wirth, the second oldest restaurant in Boston, has been serving sausage and beer (except during that silly prohibition era) since 1868.
I ate lunch at Jacob Wirth my last day in Boston, and it was the best decision I made during my visit. Of course, oysters are a New England staple, so many visitors opt to dine at Union Oyster House. If you like traditional German cuisine, without a doubt, you should also stop into Jacob Wirth for a wurst with sauerkraut and potato salad.
Visit A Museum
With more than 40 museums in the Greater Boston area, you are likely to find one that suits your interests.
Visiting Boston with kids?
Kids will have a hands-on experience at the Boston Children’s Museum and the Museum of Science. They can see penguins and Atlantic harbor seals at the New England Aquarium, and then go whale watching on a Boston Harbor cruise. At the Harvard Museum of Natural History, they may see an emu egg hatch. Kids can also construct a LEGO building to withstand an earthquake at LEGOLAND® Discovery Center Boston in Somerville.
Interested in history?
Visit the Boston Tea Party Ships and Museum to dump tea into the harbor like the colonists did. Then stop along the Freedom Trail at Paul Revere’s home, where the silversmith left for his infamous “Midnight Ride.” To see more Paul Revere silver and Revolutionary War relics, visit the Americas collection at the Museum of Fine Arts. Skip ahead to the 20th Century to view Oval Office decor and Kennedy family photos at the John F. Kennedy Presidential Library and Museum.
Want to view art?
No matter which era or medium you enjoy, I highly recommend visiting the Museum of Fine Arts. The museum has one of the largest collections in the United States with more than 450,000 works of art. If you enjoy modern art, the Institute of Contemporary Art has a unique permanent collection and rotating exhibits in a stunning waterfront building with floor to ceiling harbor views in Boston’s Seaport District. Art lovers will find even more at the Harvard Art Museums in Cambridge.
Dine In The North End
You absolutely must visit the North End while in Boston. Eat some pasta, drink some wine, get a cannoli and thank me later. Walk along Hanover and Salem streets, and you’ll find Italian eatery after Italian eatery. The restaurants all seem to post their menus outside, so you can just stop once one sounds appealing.
My friends and I ended up at L’Osteria, where I had a delicious lobster ravioli in creamy vodka sauce. If you are looking for an after-dinner treat, stop by Mike’s Pastry or Modern Pastry for cannoli. In fact, why not do a cannoli taste test by visiting both like my friends at Diapers On A Plane did!
Take A Scenic Stroll
Now that you’ve taken a tour, visited a museum and dined around Boston, you can wander. Boston is wonderful for wandering. It’s a fairly small “big city” at 48 square miles, so a 30-minute walk could take you past Back Bay rowhouses, ritzy Newbury Street shops, and Beacon Hill’s charming brick and cobblestone streets.
You could also stroll along the Charles River Esplanade or through Boston Public Garden and Boston Common. If you are walking through Boston Public Garden with children, be sure to find the “Make Way for Ducklings” statue near Charles and Beacon streets and take a ride on a Swan Boat.
Where To Stay In Boston
While visiting Boston, I stayed at the stylish Revere Hotel in Boston’s Bay Village. This modern boutique hotel is a short walk from Boston’s theatre district, Boston Common, Boston Public Garden, and Jacob Wirth for delicious German cuisine and beer. You can see how other travelers rated the Revere Hotel Boston Common, check room rates for your travel dates, and even book your room on TripAdvisor.
On my last night in Boston, I wanted to experience the city like a local, so I booked a Back Bay apartment through Airbnb. From my rowhouse apartment I walked to Trident Booksellers & Cafe for an afternoon latte and book browsing and then met up for drinks with a friend from high school at Back Bay Social Club. If you want to experience Boston like a local too, you can get $40 off your first Airbnb booking with my invitation link.
Save this post to Pinterest!
Disclosure: As a Women in Travel Summit attendee, I took the On Location Tours’ Boston TV & Movie Sites Tour for free and received a pretty rad swag bag. This post also contains some affiliate partner links. Booking a hotel or purchasing a product from one of these links — at no extra cost to you — helps to support this blog. I only share hotels and products I truly recommend and have or would stay at/use myself. As always, I strive to share accurate information and fair and honest opinions about my experience. I was not otherwise compensated for this post.