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With historical 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 on 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, and I finally visited in March 2015 for the Women in Travel Summit (WITS).
Although I was there for 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 during 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. In fact, I rode the T on my first Boston tour!
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 take a photography tour.
On Viator, you’ll find guided photography tours of the Freedom Trail and the Beacon Hill and Back Bay neighborhoods. I’d love to do this on my next visit. I’m just not sure how I’d choose which tour to take!
Though I love walking tours, I also suggest considering bus tours — such as the Boston Hop-on Hop-off Trolley. Bus tours tend to cover a broader area, giving you an idea of 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.
Of course, sightseeing tours are best if you are interested in seeing all of Boston’s top sights in a short time frame. Boston Duck Tours, which traverses 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 few 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:
- 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 Copp’s Hill Burying Ground, where Cotton Mather, known for his involvement in the Salem witch trials, is buried. Book your tour now!
- Boston Movie Mile Tour — See famous movie and TV locations around Boston on a 1.5-hour walking tour! You’ll have a drink at the original Cheers bar, stroll through Boston Public Garden to see the famous benches from Good Will Hunting and Ted, and discover more movie and TV connections in Boston. Don’t miss out — reserve your tour today!
- Boston’s North End Pizza and History Walking Tour — Learn a bit of North End and Freedom Trail history as you taste three slices of pizza and a Modern Pastry cannolo! Reserve your slice(s) by booking your tour now!
Foodie Tours Around Boston
My first tour in 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 the women-owned Bantam Cider.
Our last stop was The Independent, a local pub with an excellent selection of craft beers and deliciously potent cocktails. Several women 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 several other foodie tours in and around Boston.
More Foodie Tours In Boston
- Sip of Boston Brewery Tour –– Taste up to 12 different beers on this tour of Boston’s thriving beer scene with visits to some of the city’s most iconic breweries. This tour will likely sell out, so book now to reserve your space!
- North End Secret Food Tour –– Explore the flavors of Boston’s Little Italy with brick-oven pizza, fresh pasta, classic Sicilian cannoli, and more at six stops as you walk a trail dating back to the American Revolution! This food walking tour will also likely sell out, so make your reservation now!
- Boston Underground Donut Tour — It may be known for Dunkin Donuts, but Boston has a broader doughnut scene worth exploring (and tasting). On this tour, you’ll sample Boston’s finest doughnuts as you walk through Boston’s Financial District, Boston Public Market, and Little Italy. Like all the foodie tours I’ve recommended in Boston, this one also quickly sells out. Grab your ticket(s) now for this tasty tour!
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!
On Locations Tours also offers the 1.5-hour Boston Movie Mile Walking Tour and a three-hour private tour with your own driver/guide. The private tour covers many of the filming locations I visited on my tour.
Eat One Of Boston’s Classic Dishes (Or Desserts)
Once you have toured the city, you’ll have worked up an appetite. Luckily, Boston is full of restaurants serving delicious dishes.
And, none has done that longer than America’s oldest restaurant. At Union Oyster House, established in 1826, you’ll find freshly shucked oysters and the New England Clam Chowder for which this iconic Boston restaurant is known. As a favorite of the Kennedy family, JFK was known to privately dine upstairs. If you dine here, don’t miss the booth dedicated to the 35th president!
Of course, being situated along the Atlantic Ocean, Boston is known for its seafood. So, you probably want to know where to find the best lobster roll, right? The good folks at Thrillist compiled this handy list of the best lobster rolls in Boston. Happy lobstah eating, friends!
However, lobster rolls, oysters, and clam chowder aren’t the only famous Bostonian foods. Among other signature Boston dishes are Boston Cream Pie, which originated at the Parker House Hotel, and the baked beans for which Boston earned its nickname “Beantown.”
During my trip, I made it my mission to try a true New England Clam Chowder and a Boston Cream Pie. I knocked them both off my list when dining at Legal Sea Foods, a Boston-based seafood restaurant chain. Next time, I’m hunting down lobster rolls, pizza, and cannoli! How about you?
Visit A Museum
Visiting the Museum of Fine Arts, Boston was a highlight of my Boston trip. Seriously, I could have spent an entire day moseying between galleries. I just couldn’t get enough of the Van Gogh, Monet, and Degas artwork. And with more than 40 museums in the Greater Boston area, you are likely to find one that also suits your interests.
Best Boston Museums for 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 with experts from the Whale Center of New England. At the Harvard Museum of Natural History, they can learn about animals from around the world, or visit live animals at the Franklin Park Zoo. In nearby Somerville, future engineers can construct a LEGO building to withstand an earthquake at LEGOLAND® Discovery Center Boston.
Pro Tip: If you plan to visit the New England Aquarium, Boston CityPASS® could save 47% off your admission. The pass also covers admission to three other Boston attractions including the Museum of Science and two attractions of your choice from the following: Harvard Museum of Natural History, Franklin Park Zoo, or a harbor cruise.
Boston’s Best Historic Sites and Museums for History Buffs
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. Afterward, skip ahead to the 20th Century to view Oval Office decor and Kennedy family photos at the John F. Kennedy Presidential Library and Museum.
Art Museums in Boston
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 contemporary 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, finish with 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 the family travel bloggers 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, find the “Make Way for Ducklings” statue near Charles and Beacon streets and ride on a Swan Boat.
Where To Stay In Boston
While visiting Boston, I stayed at the stylish Revere Hotel Boston Common. This boutique hotel in Boston’s Bay Village neighborhood has had a makeover since my stay. It’s in a convenient location for travelers hoping to stay only a short walk from Boston’s theatre district, Boston Common, and Boston Public Garden.
On TripAdvisor, you can see how other travelers rated the Revere Hotel Boston Common. Like what you see? Check availability and book your stay now!
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.
Find lodging for your upcoming Boston trip using the map below!
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Save the image below to your Boston travel board on Pinterest!
Photo credits: Boston Public Garden (© SeanPavonePhoto/Adobe Stock), Acorn Street (© lunamarina/Adobe Stock)
Kassie- The Fly Away Life
I’m from Boston and I love love love seeing my city from an outsiders perspective. You uncovered things I haven’t been to like Jacob Wirth. I will have to check that out next time that I am home 🙂
I am from Pennsylvania. Both of our daughters have lived in Boston so I have learned to know the city. By far – one of my favorites stops is the Boston Public Library at the Copley green line stop. It’s so beautiful! My three favorite tours are – The PhotoWalks tour with Saba (the best) – The Harvard tour – and the Civil War tour. My husband always recommends the Harpoon beer tour. There are many good choices to get ice cream but Toscanini’s is worth the visit. (the redline & get off at Central Square)
There is so much to do in Boston, Kim, and I love all of your suggestions here. I must visit again! Also, I agree with your husband about the Harpoon brewery tour. It’s a fun tour, and you have to get a pretzel in the beer hall!
I definitely need to put Boston on my list of cities to visit. With my love of history I find from your post that there is a lot thar would interest me…so much so that I think I will need to visit more than once to take it all in. Looking into various tours offered is an especially good suggestion as a place to start taking in the sites. Your pics are amazing!
This is a great list. There is so much to do in Boston, you need to make sure to have enough time when you are there as depending on your own interests you will have days and days of things to do and this is just the start!
Yes, that is so very true. This list is just to dip your toes into the Charles River. If you are going for a week or a return visit, you can really delve into all that Boston offers, which is a whole lot!
I would totally want to visit Cheers. Did you eat there?
I didn’t go inside the Cheers bar, but some of my friends went in for a beer. It’s right across from Boston Common, so it’s very easy to find.
I need to visit. I was actually born there and have been a few times, since we still have close relatives there, but I have only been back to the city rarely. I did go back in 2013 to visit a friend when I was there for my cousins wedding but we only had dinner and didn’t get to explore as much as I would want to.
Next time you visit the Boston area, I’d be happy to give you my full recommendations. The short list is visiting the Museum of Fine Arts, strolling through Boston Public Garden, and eating dinner and a cannoli in the North End.
This looks like so much fun! The hubs and I haven’t visited Boston yet, but everything looks awesome (minus their baseball team…#Yankees4Life). I love doing all the historic sightseeing tours so this is right up my alley! I will have to pin this for future reference.
If you like history tours, Boston definitely is worth visiting. The city is full of historic sights!