- Skip to right header navigation
- Skip to main content
- Skip to primary sidebar
MY WANDERLUSTY LIFE
#TimeBudgetTravel
The Only Boston Bucket List You Need: 65+ Best Uniquely Boston Experiences (w/ Pro Tips!)
Last Updated: January 12, 2024 // by Ashley Smith 18 Comments
Having lived in Boston for over a decade, I’ve been working on my own Boston bucket list for quite some time now. I can tell you firsthand there are so many unique Boston experiences you shouldn’t miss while you’re here!
Now, I live here but I’m not from here, which means I’m still able to see the city through the eyes of a tourist like yourself . But, I also have the lowdown on all the most unique Boston experiences you don’t hear about every day. ( And great tips on easy ways to save money on your trip to Boston !)
I often have friends and family visit me so I’m constantly checking off, adding onto, and refining my own Boston bucket list. So, from the blog of a local with the eyes of a tourist, I’ve created this Boston bucket list for you with 65+ of the best things to do and see in Beantown!* (in no particular order)
*No one calls it “Beantown.” Ever.
Table of Contents
1. Tour the Sam Adams Brewery
Something I’ve found to be on everyone’s Boston bucket list is a visit to the Sam Adams Brewery . Arguably the most famous beer out of Boston, Sam Adams offers free tours of its original Boston brewery that include free beer ! Plus, you get to keep the tasting glass as a souvenir! After your tour, hang out in their on-site taproom and beer garden. (Yes, they serve big Bavarian pretzels too.)
I’ve done this with every single person who has visited me over the past decade. I’m drowning in tasting glasses at this point, like most other Bostonians. Need to know: The tours are “free” but they do ask for a $2 donation to their selected local charity.
Boston bucket list pro tip:
If you’re not able to make it out to the original brewery in Jamaica Plain, stop by the shiny new Sam Adams Boston Taproom at Faneuil Hall. You can enjoy a long list of Sam Adams beers here, many of which are exclusive to this particular location! (No tours at this location though.)
2. Visit the Isabella Stewart Gardner Museum
One of the most beautiful and unique museums on your Boston bucket list is the Isabella Stewart Gardner Museum . Modeled after a 15th-century Venetian palace, this museum houses European, Asian, and American paintings, sculptures, tapestries, and much more.
The museum is a masterpiece in itself—all designed around a central courtyard filled with mosaics, flowers, greenery, fountains, and such. You’ll feel like you’re in Europe rather than Massachusetts.
The most interesting part about this museum though? Its role in one of the biggest mysteries in Boston history—the 1990 art heist that has yet to be solved. (You can still see the empty frames where the stolen paintings used to be.)
Want to learn more about the museum and this incredible mystery? Watch the 2021 Netflix series This Is a Robbery . It’s such a good primer for your visit.
Admission to the Isabella Stewart Gardner Museum is FREE if your name is “Isabella” or if it’s your birthday!
3. Visit the New England Aquarium
The massive New England Aquarium is one of the best in the country and definitely worthy of your Boston bucket list. The aquarium consists of tons of exhibits, all surrounding their Giant Ocean Tank—a four-story coral reef with hundreds of animals including the famous Myrtle the sea turtle. My favorite exhibit? The penguins and harbor seals, without a doubt!
Need to know:
Admission to the New England Aquarium is included in the Boston CityPASS . I am such a big fan of the CityPASS and I use them in every city they’re offered. They save you money, let you skip the line, and include other discounts. Definitely pick up a Boston CityPASS to save money and time on your Boston bucket list!
Pick up your Boston CityPASS here.
Also, the NEAQ is incredibly committed to marine animal conservation, education, scientific research, and more. I wouldn’t recommend this place if they weren’t one of the good guys. Follow this link to learn more about what you need to know about wildlife tourism .
If you can’t fit an aquarium visit into your schedule, you can still stop by and see the adorable harbor seals showing off in their outdoor habitat totally free.
4. Go whale watching
One of the great activities the New England Aquarium offers are fantastic whale watching tours —a must for any Boston bucket list. There is nothing cooler than watching humpback whales leaping out of the water right next to your boat.
Whale sightings are totally guaranteed since Boston is located near one of the world’s most active marine sanctuaries. They have marine biologists on board to teach you all kinds of cool stuff during the trip.
Plus, your trip on the whale watching boat will get you views of the beautiful Boston skyline you can’t get anywhere but from the water.
The Aquarium’s on-board naturalists not only teach you about marine life, they also photograph it as a means of documentation. As a bonus, they post their incredible photos and notes online after every tour so you can see “your” whales up close in ways you couldn’t capture on your phone.
Book your NEAQ whale watching trip here.
Many items on your Boston bucket list likely take place on the water. If you suffer from motion sickness as I once did, take a look at my post on the permanent motion sickness cure I found that cured me for good!
5. Throw tea into the harbor at the Boston Tea Party Museum
One of the most fun attractions on your Boston bucket list will be the Boston Tea Party Ships & Museum . I’ll admit I thought this was going to be a lame tourist trap when my out-of-town friends wanted to visit. However, I was more than impressed by this museum!
You’ll learn all about the events of the Boston Tea Party from live reenactors, get to tour the full-scale replica ship, take part in interactive exhibits, and… wait for it… throw chests of tea into Boston Harbor! High treason is so. much. fun.
Then , you get to visit the museum which is so cool but we have the potential for many spoilers here so I’ll just leave it at that. If you visit one historical museum in Boston, make it this one. Huzzah!
Get your Tea Party Museum tickets here.
The Boston Tea Party Museum and ship are ADA accessible. Wheelchairs and ASL interpreters are available upon request.
If you’re brave enough to visit Boston in December you can witness a full-on reenactment of the Boston Tea Party each year on December 16th. Complete with angry mobs of colonial women in the streets, a meeting at the Old South Meeting House to protest the tea tax, a fife & drum corps march through the city, and tons of tea being dumped into the harbor, all for your viewing pleasure. (Don’t miss it!)
6. Have a beer at Cheers
Yes, that Cheers! But also, not quite.
The hit 80s/90s sitcom Cheers was set at a bar in Boston that was inspired by a real Boston bar called the Bull & Finch Pub. Today, the bar is officially called Cheers and is open for food and drinks and for all your Cheers souvenir needs.
Cheers looks exactly like it does in the TV show… on the outside. The inside? Not so much. Having a beer at Cheers is a must on any Boston bucket list, but do know that the inside looks nothing like the bar you see on TV. This shocks everyone.
7. Take the Boston Old Town Trolley Tour
The Old Town Trolley tour of Boston is another one of those “touristy” things to do in Boston that totally surprised me.
I ended up on the Boston trolley tour when our July 4th Red Sox game got rained out. Soaking wet we jumped onto an Old Town Trolley tour and had the best time. Even as a resident I learned so many Boston fun facts and laughed my ass off.
The Trolley tour guides are so fun and you get to see so much of Boston in such a unique way. (I took the Old Town Trolley tour during my day in St. Augustine as well but it wasn’t nearly as fun and entertaining as the one in Boston.) I highly recommend adding this to your Boston bucket list!
You can take the full Boston tour, or enjoy the Boston Old Town Trolley’s hop-on hop-off capabilities ! Use the trolley as your transportation around town to many of the sites on this Boston bucket list, all with one affordable pass.
Book your Old Town Trolley tour here.
8. Explore the Boston Public Gardens
Just across the street from Cheers is the Boston Public Garden , established in 1837 as America’s first public botanical garden. If it’s a nice day out, this is a perfect place to spend it.
At the Boston Public Gardens you’ll find:
- Boston’s famous swan boats
- the bench from Good Will Hunting
- the Victorian bridge and lagoon
- monuments and fountains
- the also famous Make Way For Ducklings sculpture
- tons of floral arrangements and over 80 species of plants
- a large, beautiful park that’s perfect for picnics (I can say that because I’ve done that)
- and most likely a wedding party photo shoot or two happening. Actually, I can pretty much guarantee that.
9. Hang out in Boston Common
Just next door to the Public Garden is Boston Common and yes they’re different. While both are sprawling public parks, Boston Common (America’s first public park) is actually much older having been created in 1634.
The Common was once a grazing ground for cattle and the location of many-a public hanging and militia formation. Now, it’s mostly for people looking to hang out, play sports, run/walk/skate, and much more.
If you’re driving into Boston and need a decent place to park, the Boston Common Garage is where I always park because it’s clean, well-lit, and doesn’t cost a month’s salary to use.
10. Find famous graves at Granary Burying Ground
A block from Boston Common you’ll find Granary Burying Ground and the gravesites of many famous Bostonians like:
- John Hancock
- Paul Revere
- Samuel Adams
- Benjamin Franklin…’s parents
- the victims of the Boston Massacre
- Robert Treat Paine, also a signer of the Declaration of Independence, unfortunately not a doctor
- and many more.
Granary Burying Ground is a perfect example of the kind of interesting, centuries-old cemeteries you’ll find here in Boston. Be sure to read the headstones and check out the designs and artwork on them. It’s… unique.
On the weekends, volunteer history enthusiast Jimmy Cole will offer you an informational folder on the cemetery and those buried within. Insert a couple dollars into the folder (if you feel so inclined) and return it upon exiting.
11. Have a beer at the Beantown Pub
The Beantown Pub * is right across the street from Granary Burying Ground. Besides being a typical Boston pub, this is one of the few places you can find Sam Adams Brick Red on tap.
Brick Red is an Irish red ale that you can only find at a handful of bars in Boston… and nowhere else. So if you want to try an exclusive Boston beer, stop in here. Also, the food is pretty good.
*OK this is the only time you’ll see or hear the term ‘Beantown.’
However, the reason I’ve added it to your Boston bucket list is because of a special tradition. Because of this bar’s location, you can see the graves across the street. Therefore, the Beantown Pub is known for being the only place where you can “drink a cold Sam Adams while looking at a cold Sam Adams.” Callous, I know, but it’s tradition.
12. Get Boston Cream Pie from the place it originated
One block from the Beantown Pub is the Omni Parker House, a historic luxury hotel known for being the birthplace of Boston Cream Pie . If that’s not Boston bucket list worthy, I don’t know what is.
You can reserve yourself a fancy dinner here in Parker’s Restaurant (FYI: dress code) or you can simply stop into Parker’s Bar any time of day and order yourself a Boston cream pie.
The Omni Parker House Boston cream pie is smothered in shaved almonds. (Therefore, I, with my hostile almond allergy, merely watch as my friends and family consume them.) However, they did tell me that if you call ahead at least 24 hours, they’ll make you one without almonds.
13. Look for Charles Dickens’ ghost
The Omni Parker House Hotel is beautiful and old and… said to be one of the most haunted places in America. Back in the late 1800s, Charles Dickens actually called this hotel ‘home’ for a time. In his suite was a large mirror in front of which he would practice his readings for hours on end. That mirror now hangs in the hallway of the Omni Parker House Hotel.
They say if you look hard enough, you just might see Dickens as he practiced a ‘Christmas Carol;’ or that if you take your picture in the mirror you might see something eerie. Try it out for yourself. Read more about the Charles Dickens mirror here.
14. Take a ghost tour of haunted Boston
In a city as old as Boston, you know we’ve got some great ghost stories! Ghost tours of Boston are some of the most popular tours in town.
You get to explore some of the city’s hidden alleyways and burial grounds and learn the creepiest stories from Boston’s past. #truecrime Come to the dark side, we’ve got lobster rolls.
Book the Ghosts & Gravestones tour here. (It’s very popular!)
15. Visit the Boston Massacre Site
In front of the Old State House you’ll find a large round memorial plaque marking the location of the Boston Massacre. Remember hearing about that in school? Take this opportunity to actually learn what happened. (I personally didn’t know until I went there either.)
Fun fact : The Old State House was once the tallest building in the city. I mean, WOW. Look at her now.
16. Grab lunch at Quincy Market
If you should find yourself hungry anywhere in the vicinity of Faneuil Hall while checking off your Boston bucket list, head to Quincy Market . Opened as a public market back in 1826, Quincy Market now houses hundreds of food stalls of all varieties.
Quincy Market can get crowded and seating is limited. Instead, take your food down the street to the Greenway and enjoy it in a breezy, beautiful, uncrowded spot.
17. Visit Paul Revere’s House
Tucked back into Boston’s North End you’ll find Paul Revere’s House , built in 1680, now a small museum. This is where Paul Revere was living when he set out for his “midnight ride” to let everyone know “the British are coming!” (though he never actually said those words)
The Paul Revere House is now the oldest building in downtown Boston. A few bucks will get you inside where you can visit a couple of the rooms and learn a lot about this super interesting historical figure.
18. Tour the Old North Church
Naturally, next up on the Boston bucket list is a tour of the Old North Church . Well, that really only makes sense if you know a thing or two about Paul Revere already.
Long story short, Paul Revere was alerted to how the British were coming by the lanterns atop the Old North Church. “One if by land, two if by sea”—one lantern was to be lit if they were arriving by land, two lanterns if they were rowing over from across the Charles River.
The Old North Church today is a perfect example of a Colonial-era church, with its private boxes and lack of décor.
You can now visit the Church’s underground crypt on a guided tour on Fridays and Saturdays for $5. (Over 1,100 people were buried down there.)
19. Pay your respects at the Holocaust Memorial
The New England Holocaust Memorial is a big beautiful tribute to the 6 million Jews killed in the Holocaust. It’s located just off the Freedom Trail near Faneuil Hall and is bursting with symbolism.
The NEHM has just released new technology for your visit. At the memorial you can scan a QR code to activate a free nine-stop guided tour of the memorial that’s full of interesting information.
Discover more Boston World War II sites here. (Psst… I’m also a WWII historian!)
20. Hop aboard the USS Constitution
The USS Constitution (also known as Old Ironsides ) is a wooden-hulled, three-masted US Navy ship first launched in 1797. Today it’s the world’s oldest ship still afloat as it has never lost a battle.
You can climb aboard the ship and visit the USS Constitution Museum in the Charlestown Navy Yard. Hanging out on an 18th-century tall ship in Boston Harbor? Such a Boston bucket list item. (There’s also a World War II destroyer too if that’s more your speed.)
The USS Constitution fires its cannons every morning and every night as it has done for over 200 years. If you get the chance to experience this, get yourself to the ship! The boom is LOUD and definitely gives you an idea of what an 18th-century battle must have sounded like.
21. Climb to the top of the Bunker Hill Monument
The Battle of Bunker Hill was one of the first major battles of the Revolutionary War. It was also one of the most important because, even though the British won, it showed how strong the American militia was against such a powerful enemy.
Just five years later the construction of Bunker Hill Monument began. Today, you can climb to the top of the monument for awesome views of Boston, to learn about the battle from National Park rangers, and visit the Bunker Hill Museum, all for free.
The only way to the top of Bunker Hill Monument is via 294 stairs. There are no elevators. However, there are multiple 360° live cameras at the top so you can see the views.
Reward yourself for the climb with an ale at the nearby Warren Tavern . This historic tavern was built in 1780, has served George Washington, and was a favorite of Paul Revere. George Washington’s funeral speech was given here. You’ll really feel like you’ve stepped back in time.
22. Walk the Freedom Trail
Probably the most well-known “thing to do in Boston” for visitors is the Freedom Trail . The Freedom Trail, a literal marked path through the city, starts at Boston Common and ends at the Bunker Hill Monument, stopping at notable historical sites along the way, including (but not limited to) the last 12 items on this Boston bucket list.
If you have only one day in Boston and want to see the historical sites, walk the Freedom Trail. It’s totally free to do on your own though they do offer guided tours with period reenactors . (It is not uncommon to see a Minuteman just walking around Boston or a Redcoat sitting at a bar.)
I love the Freedom Trail and it’s another thing I’ve done about 20 times, with everyone who comes to visit. It’s a great introduction to Boston’s history and neighborhoods and it’s FREE.
Book your guided Freedom Trail tour here, or opt for this VIP version which includes a visit to the Old North Church steeple and Paul Revere’s home.
23. Check out the Boston Bricks
In a small alleyway not far off the Freedom Trail you’ll find the Boston Bricks, a unique art installation that also showcases Boston’s character and some of its biggest historical contributions. They are a total secret you’d never find if you weren’t looking for them!
Find the Boston Bricks: Winthrop Lane, between Arch and Otis Streets
24. Have dinner in the North End
If you have only one meal in Boston, make it a dinner in the North End, Boston’s Italian district. Often called “Little Italy” (by people who don’t live here), Boston’s North End is about as close to being in Italy as you can get here in the US.
Dinner in the North End should be high on your Boston bucket list and you really can’t go wrong at any restaurant here. My last dinner here was at Bacco and it was fabulous (and my last lunch was at Ristorante Lucia ). Other favorites include:
- La Famiglia Giorgio’s
- Antico Forno
- or just wander through the North End and browse menus as you go. Don’t be afraid to wander off Hanover Street.
Dinner in the North End can be expensive – check out this post on visiting Boston on a budget to see where you can shave some cash!
25. Pick a Pastry Shop
Now comes the hard part: picking your North End pastry shop. In the ongoing cannoli wars of the North End there are two major contenders:
- Mike’s Pastry
- Modern Pastry
…and the topic can be quite polarizing. Each is equally popular, though Mike’s is the most well-known. Both offer similar treats, but with their own take. Both will have lines down the block.
Personally, I’m on #TeamMike’s. But, I should mention that cannoli aren’t my go-to order. Many say the cannoli at Modern Pastry are better, and I can’t argue with that.
However, my go-to order and the one I absolutely recommend to you is a lobster tail—large, flaky pastry filled with delicious fluffy cream, all covered in powdered sugar. Following up a lobster roll with a lobster tail = big time Boston bucket list experience.
The lobster tail at Mike’s outperforms the one at Modern, no question. (The filling is fluffier. The filling at Modern is more custard-y.) But again, much of this is personal opinion–bring on the hate mail.
Both Mike’s and Modern are cash-only establishments. Do not wait in those long lines and try to pay with a credit card.
The pace at Mike’s is fast and frenetic and single file lines are virtually nonexistent once you enter the shop. It can be quite chaotic. Modern has a relatively more “orderly” system and you can even grab one of the few tables inside for table service.
Also, Modern Pastry is unique in that it also has a speakeasy-type bar hidden underneath it. Inside, to the right of the counters you’ll find a staircase that takes you to the Modern Underground (where you’ll also find the restrooms).
26. Take a North End food tour
Ok, so maybe you want to try a little bit of everything while here? In that case, take a small-group walking food tour of the North End.
You’ll get to explore this historic neighborhood while sampling fabulous Italian staples. Plus, you get to tour the Old North Church, see the Harbor, and all with a dedicated local guide. Get more details here:
Book your North End food tour here … or opt for the Ultimate Boston Food Tour : Freedom Trail & North End.
27. Attend St. Anthony’s Feast
If you visit at the end of August, check out St. Anthony’s Feast in the North End–New England’s largest Italian festival. This annual festival is such a fun way to explore Boston’s North End and enjoy all things Italian.
There’s music, parades, and parties, but perhaps the best part is the amazing food from the 100 street vendors. I even had the best lobster roll of my life here.
28. Stroll along the Boston Harborwalk
Winding its way from the North End to the Seaport district is the most popular strip of the Boston Harborwalk , a delightful trail along the harbor.
You’ll get to see all the beautiful yachts and sailboats and marine birds, visit the harbor seals at the aquarium, hang out in beautiful parks, have drinks and snacks at the fun harbor-side restaurants, and more. Prepare for fabulous Boston photo ops.
29. Fill up at Haymarket
The Haymarket is one of America’s oldest open air markets—nestled in between the North End and Faneuil Hall. You can find fresh, local fruits, vegetables, and seafood—both for taking home or enjoying right there.
It’s hustle, it’s bustle, and it’s a unique Boston experience worth checking out. Do not miss the oyster vendors—great oysters at a killer deal and much entertainment to boot! Need to know: The Haymarket only operates on Fridays and Saturdays. The earlier you go, the better. (But the later you go, the cheaper.)
30. Try your hand at candlepin bowling
Did you know bowling is different here in New England? Yes, the same bowling you’ve played your entire life. Here in Boston we have candlepin bowling and it’s quite different from what you’re used to!
- Small, coconut-sized balls with no holes
- Tall skinny pins
- You get three rolls per turn instead of two
- The pins don’t reset in between; you just roll again with all the pins you knocked down laying around
Now that I’ve lived here so long, I’ll totally fight you that candlepin is better. (It’s definitely more challenging though.) Try out candlepin bowling for yourself at Boston Bowl and see how you like it! They have “regular” bowling too and they’re open 24 hours. (Here are all the other places you can go candlepin bowling in Massachusetts .)
31. Check out the Boston Public Library
The Boston Public Library is one of the most beautiful spaces in equally beautiful Copley Square. You’re welcome to enter and walk through the space, no actual reading required.
The architecture alone is worth a visit, as well as the incredible frescos and artwork; the famous Bates Hall; the courtyard garden; and the café and tea room.
If the Boston Public Library is high up on your Boston bucket list, you might be interested in one of their free guided tours where you can learn about the library’s history and architecture, its famous artworks, and interesting details you wouldn’t learn otherwise.
32. Attend a Red Sox game
No Boston bucket list would be complete without a game at historic Fenway Park, home to the Boston Red Sox.
Whether you’re a big sports fan or not, a Red Sox game is such a great way to experience so much of what Boston is about. It’s loud and fast, exciting from start to finish, the outside vendors are non-stop entertaining, and you’ll have such a great time.
33. Tour Fenway Park
If the Sox are out of town or you visit off-season, don’t worry! Another popular Boston Bucket List activity are the guided Fenway Park tours , which you can do all year long, in every kind of weather. My friends have all loved their Fenway tours!
Book your guided Fenway Park tour here.
34. Check out all the other Boston sports
Being the ridiculously serious sports town Boston is, your Boston bucket list shouldn’t stop at baseball. Depending on when you visit, you can also take in a:
- Boston Celtics NBA basketball game
- Boston Bruins NHL hockey game
- New England Patriots NFL football game (about 45 minutes outside the city but accessible from downtown via the Commuter Rail)
- New England Revolution MLS soccer game (also at Gillette Stadium in Foxboro)
35. Go kayaking on the Charles River
The Charles River is such a huge piece of Boston—you’ll have your eyes on it almost everywhere you go—and seeing the city from the water is such a cool Boston bucket list experience.
On warm summer days the river is one of the most popular places to be in Boston. You can kayak, canoe, or paddleboard, see Harvard and the Boston skyline from the water, all in an easy-to-paddle section of the river.
You can even take guided kayaking tours with different areas of focus: Boston Harbor, skyline and sunset tours, and more! Check out Paddle Boston for more information.
36. Tour the Harvard campus
Many visitors to Boston have a visit to the Harvard campus on their Boston bucket list. The Harvard area is both beautiful and world famous and well worth a tour of your own. (Yes, you’ll get to visit Hahvahd Yahd.)
These super popular informational and entertaining Harvard campus tours are led by current Harvard students and will take you to many of the school’s most notable and historic sites. Pick up a sweatshirt while you’re there then feel free to explore the area on your own afterwards.
Book your Harvard campus tour here.
37. Have a drink at the Miracle of Science
Looking for more nerdtastic ways to spend some time in Cambridge? Leave Harvard and hit up MIT! Stop by the Miracle of Science for food, drinks, and geeks.
Order from their periodic table menu, sit at bona fide lab benches on lab stools, and take shots out of graduated cylinders.
38. Walk the Black Heritage Trail
The Black Heritage Trail is a 1.6-mile walking tour through Boston’s Beacon Hill neighborhood that explores the most important sites of the area’s African American history. The National Park Service offers free, 90-minute guided tours.
You’ll visit 14 sites that include: former homes, schools, businesses, churches, the African Meeting House, several stations of the Underground Railroad, and the Museum of African American History.
39. Check out Acorn Street
Historic Acorn Street is just one small alleyway in Boston’s Beacon Hill neighborhood but it’s known as one of the most photographed streets in America.
Paved with river stones, lined with million-dollar red brick townhouses, and accented by American flags and green ivy, Acorn Street is iconic Boston. It sits right in the center of downtown Boston but feels a world (and centuries) away.
Residents are fine with you stopping by to take a quick photo or two, but do not by any means set up a full-on Instagram photo shoot. Don’t sit on their stoops, invade their privacy, or touch anything . Please always Instagram respectfully!
40. Stroll Newbury Street
Located in Boston’s Back Bay neighborhood, Newbury Street is the area’s popular shopping district. You’ll find high-end shops, restaurants and wine bars, beautiful historic brownstones, and more.
Whether or not you’re into shopping when you travel, Newbury Street is still a great place to stroll on a nice day in Boston. Grab a drink at one of the outdoor patios, marvel at the historic architecture, or just wander. (I personally love checking out what all the residents have done with their tiny little garden plots.)
41. Have a drink at one of the USA’s oldest taverns
The Bell in Hand Tavern opened in 1795 and has been one of the most famous Boston alehouses ever since. Conveniently located just off the Freedom Trail and Faneuil Hall, you can pop in for a drink and some chowder and feel like you’re back in the 18 th century (as you will many times while checking off your Boston bucket list).
42. Take a sunset dinner cruise
I’m a big fan of harbor cruises, and getting out on the water is a must for your Boston bucket list. You get to enjoy great food, see the city’s skyline from the water, dance, drink, play games, and more!
I’ve been on a couple of these Boston dinner cruises and they are such a unique, fun time. (They also have lunch cruises !)
Book your sunset dinner cruise here.
43. Ferry out to the Boston Harbor Islands
Boston’s waterfront location means there are endless opportunities to get out on the water—and one of the coolest ways to spend a summer day here is by taking the ferry out to the Boston Harbor Islands .
Choose an island and you can explore miles of walking trails, check out old forts, spend the day on the beach or in the many parks, go camping, explore tide pools, and much more. All within view of the Boston skyline.
44. Take a day trip to Salem
Arguably one of the most popular day trips from Boston is up to Salem, Massachusetts. Known for its witches and other spooky things, Salem is such a fun addition to your Boston bucket list.
There are tons of witch-centric things to see here like the Salem Witch Museum (great for learning about the Salem Witch Trials), the haunted history tour , the Salem Witch House, and the chance to visit to all the Hocus Pocus filming locations .
But there’s much more to Salem like the House of the Seven Gables, the Salem Maritime National Historic Site, and my favorite, Notch Brewery.
Don’t miss the Salem in a Day from Boston tour : The Legacy of Witches, which includes roundtrip transportation to and from Boston.
Salem is about 45 minutes north of Boston but you don’t need a car to get there–you can take the high-speed ferry from Boston to Salem in the same amount of time. Many of my visiting friends have done this and they all loved it. Plus, as I’ve said tons of times, getting out on the water in Boston is a must!
Get your Salem ferry tickets here.
45. Visit the Museum of Fine Arts
If you love art museums, definitely put the Museum of Fine Arts on your Boston bucket list—it’s one of the top 50 most visited museums in the whole world.
Here in this huge, beautiful museum you can check out paintings from such famous names Monet, Van Gogh, Rembrandt, Goya, Renoir, and more. You can see Egyptian artifacts and artworks from Asia, Africa, the Americas, Europe, and the Ancient World.
46. Check out the Mapparium
One of the more unusual spots on this Boston bucket list is the Mapparium at the Mary Baker Eddy Library. Step inside a 3-story, stained glass globe and enjoy a 3D perspective of the world in 1935. The experience also involves narration, music, and LED lights.
47. Check out the awesome downtown beer gardens
Boston only has a short window of great weather so in the summer the city absolutely comes alive—and that includes the appearance of summer pop-up beer gardens and those at the downtown taprooms. Get your drink on in some beautiful locations, hear live music, and more!
The best downtown Boston beer gardens:
- Trillium Fort Point with rooftop terrace
- Night Shift Brewing at Lovejoy Wharf , also with great food and views!
- Harpoon Brewery in the Seaport
- Sam Adam Boston Taproom at Faneuil Hall
- Trillium Garden on the Greenway – summer pop-up
- Cisco in the Seaport – summer pop-up
- Night Shift Owl’s Nest on the Esplanade – summer pop-up
48. Eat a lobster roll
One of the most popular meal items in Boston and a must for your Boston bucket list—the lobster roll. But don’t get your lobster roll just anywhere.
My 3 favorite spots to get a lobster roll in Boston: (All located in the Seaport)
- James Hook & Co.
- Yankee Lobster
- Barking Crab
There are two ways to get your lobster roll:
- Cold with mayo (kind of a lobster salad deal, all mixed together, served cold)
- Hot with butter (just lobster meat on a roll, with a side of hot butter for dunking or dumping)
Make sure to specify which one you want when you order or you might be surprised by what you get. Major pro tip here: get it hot w/butter.
49. Have dinner at Legal Sea Foods
Legal Sea Foods is a locally-based restaurant chain popular with visitors and locals alike. The food here is always great and they have locations all over Boston.
Legal Harborside in the Seaport has a roof deck for seafood + sunsets. There are even locations in the Boston airport if you missed one during your visit!
50. Get yourself a lobster at the Barking Crab
Have eating lobster the old fashioned way on your Boston bucket list? In that case, stop by the Barking Crab , also in the Seaport (notice a theme here?). This iconic Boston eatery is such a fun place to spend a night—floating on the harbor enjoying some fantastic food in open-air.
The menu here is exactly what you have in mind when you think of New England seafood. You will not be disappointed. Don’t forget to wear the bib!
51. Have drinks on a rooftop
The city of Boston is not short on fabulous rooftops (some of my favorite places to hang out!). Enjoy a brew with a view at many sky-high locations around the city including:
- Lookout Rooftop and Bar (Seaport)
- Rooftop@Revere (Back Bay)
- Over the Charles (Cambridge)
- Deck12 at Yotel Boston (Seaport)
- The Lexington (Cambridge)
- Sam Adams Boston Taproom so you can people watch in Faneuil Hall
52. Ride the Codzilla
The Codzilla is a high-speed thrill ride on a boat around Boston Harbor that I have never done because it sounds terrifying. However, the Codzilla is pretty popular and I know at a least a few people who would totally be into it. If speed + getting wet is your jam, check out the Codzilla!
Get your Codzilla tickets here.
53. Attend the St. Patrick’s Day parade
I think it goes without saying that if you visit Boston over St. Patrick’s Day, attending this wild parade is a must for your Boston bucket list!
Boston’s Irish culture is world famous and the St. Patrick’s Day Parade in Southie is unlike any other you’ll ever experience. Be sure to pack lots of green and get ready to partayyy.
54. Cheer on the runners at the Boston Marathon
Another world famous event, the Boston Marathon is the world’s oldest annual marathon. It takes place in April and is a legit state holiday here. People get work off to come and cheer on the runners… and so should you.
The best part? You’ve got a whole 26 miles of options when it comes to where to watch it! The closer you get to the finish line, the more crowded it gets.
If you’re not visiting on Marathon Monday you can still check out the painted finish line and the two memorials to the victims of the Boston Marathon bombings in 2013.
55. Spend July 4 th in the city where it all began
It shouldn’t surprise you that July 4 th in Boston is HUGE, and kinda has been for, like, centuries. There are massive parties, music performances (notably the Boston Pops), fireworks displays, and the whole city vibe is electric.
The biggest party of the summer typically takes place on the Esplanade, right on the Charles River. (In 2021 it was elsewhere because, well, you know why.)
56. Take a day trip to Lexington & Concord
So yes, the Revolutionary War started right here in Eastern Massachusetts. The first battle—and the shot heard ‘round the world —happened 16 miles northwest of the city in the towns of Concord and Lexington. Here, you can visit Minute Man National Historic Park and see where it all started.
Better yet, visit on July 4 th weekend to participate in fun reenactments and the annual reading of the Declaration of Independence. Or, visit on Patriot’s Day (also known as Marathon Monday) to watch a reenactment of the first battle of the Revolution in real time. (Costumed reenactors on horseback, this is not a drill!)
Also located in Concord: Walden Pond, from Henry David Thoreau’s Walden .
57. Ride the T – America’s oldest subway system
Throughout the city and beyond we have our local subway system called the T . You can get just about anywhere on this Boston bucket list via the T.
But the reason I’ve included it in this list is because the T is actually the oldest subway system in the United States that’s still in use. (Opened in 1897) So that’s something!
58. Stay at the Liberty Hotel
The Liberty Hotel is a higher-end hotel located in historic Beacon Hill… that used to be the Charles Street jail. It’s what I call “prison posh.” If you’re looking for a unique place to stay for your Boston bucket list, book a stay at the Liberty Hotel .
This place is so interesting and offers some of the best hotel views of the skyline and the Charles River. Plus, they have six on-theme restaurants and bars (all with authentic prison-ish detail) like:
- Clink. – fancy seafood restaurant
- Alibi – cocktail bar set in the jail’s former “drunk tank”
- Liberty Bar – popular bar scene
- Catwalk – hangout spot on the original jail catwalk (for hotel guests only)
Book your Liberty Hotel stay here. And check out my guide to picking the perfect hotel every time !
59. Enjoy dim sum in Chinatown
Boston’s Chinatown is bursting with amazing food, but the one Boston bucket list experience you need to have here is Sunday dim sum at Hei La Moon .
Try an endless number of delicious items here in this massive, fast-paced venue. If you’ve never tried dim sum at all, you’re in for one hell of an experience. If you’re a seasoned dim-sum-er, you’ll absolutely love the eats here!
Follow your meal with a walk around this cool neighborhood, pick up some bubble tea and some goodies from one of the local bakeries. Here in late January or early February? Definitely don’t miss the Chinatown Lunar New Year celebration!
60. Hang out at Castle Island
On Castle Island in South Boston you can walk the 2-mile Harborwalk, hang out on the beaches, explore historic Fort Independence, and watch airplanes take off and land at nearby Logan airport.
Castle Island is actually a peninsula, so checking out the area won’t actually require a boat. It’s a nice break from the busier city scene and not too far from the Seaport.
61. Eat fried clams and ice cream
I get it—if you’re not from here, combining fried clams and ice cream may sound seriously weird. But I’m telling you, it works!
You’ll see fried clams all over the Boston area and you should definitely try them. Follow that up with a local scoop and you have yourself a quintessential Boston bucket list summer meal. If you’re out at Castle Island, stop by Sullivan’s , a local favorite, for both (and more).
When ordering fried clams, always go with clam bellies, not clam strips. (Clam strips are so thin you’re basically just eating breading.)
62. Visit your favorite Boston filming locations
One of my favorite things to do when I travel is find myself in the same spots that I’ve seen on TV and in movies. And if you’re the same, you’re going to love Boston!
So many shows and movies have been made here in Boston—you can’t swing a cannoli without hitting a recognizable location. You can even take a guided Boston movie tour of such filming locations.
- Good Hill Hunting
- The Departed
- The Social Network
- Legally Blonde
- Mystic River
- And so, so, so many others.
See how many you can find or seek out your favorites! There’s a good chance anywhere you go in the city was featured on film.
Book your Boston movie tour here.
63. Spend a day in Provincetown on the Cape
Let me be clear here: there is no such thing as a “day trip to Cape Cod”… with a couple of exceptions, like this one. The Cape is far and long and traffic to head down the Cape in the summer is the stuff of nightmares. A day trip to the Cape is absolutely not feasible, so get that out of your head now. (Unless you book this Cape Cod day trip by boat !)
HOWEVER, there is one exception—a day trip to Provincetown via the high-speed ferry from Boston. You can go from downtown Boston to Provincetown in just 90 minutes (rather than the 2-5 hours it would take by car, depending on the day and time of year you visit.)
Provincetown is on the very tip of the Cape (the knuckles of the fist, if you will) and is every bit the quaint little Cape beach town you’re hoping for. If you’re looking to add a “day trip to Cape Cod” to your Boston bucket list, check out the Provincetown Fast Ferry for schedules and rates.
And when you’re there, take the Historic Provincetown Walking Tour : Harbor Tales & Heritage
64. Explore Plymouth
Plymouth, famous for Pilgrims and the Mayflower, makes a great day trip from Boston. If you’ve got a car , Plymouth is just a short drive, but if you don’t you can take an easy tour for the day!
In Plymouth you can visit the historic sites of the Plimoth Patuxet Museums (formerly Plymouth Plantation), see Plymouth Rock, tour the Mayflower ship, and more.
This Plymouth day tour includes your own personal guide, admission to all the sites, a stop in Quincy, free hotel pick up and drop off, and complimentary snacks and water. Check out the details below!
Book your Plymouth day trip here.
65. Pick and choose from Boston’s long list of museums
I listed my favorites in this post and the few I feel really deserve space on your Boston bucket list, but I don’t really know your personal preferences, now do I?
In fact, Boston has a long list of incredible museums of all types–art, history, culture, science, and even the JFK Presidential Library. If you find yourself in the city on an especially cold or rainy day, check out this list of Boston museums .
More resources for your Boston bucket list
- Hotels : Find great places to stay in Boston here on Booking.com (but Hotels.com and Expedia usually have good deals too).
- Rental cars : Check out the best Boston rental car deals here.
- Travel planning : Pick up a Boston or New England guidebook for the rest of your visit. And this USA customs and culture guide if you’re coming from across the Pond.
- Like this post? Have questions? Reach out on Instagram .
What are the main things on your Boston bucket list? Let me know in the comments below! Have fun in Beantown! (Just never call it Beantown.)
Save this info, pin this image:
About Ashley Smith
Ashley is a historian and Oktoberfest expert & tour guide. She has traveled to 39 countries and specializes in quick trips throughout Europe and the Americas that prioritize hiking adventures, museums of all kinds, cultural experiences, and jam-packed itineraries. She hails from Memphis, TN and currently lives in Boston with her husband and two feline sidekicks.
Subscribe to MWL
Get my 2024 Oktoberfest Party Planning Checklist here!
Free 2024 Oktoberfest Packing Checklist
Get my 2023 Oktoberfest Packing List here!
Want more Oktoberfest ?
Belize Packing List
Iceland packing list, get my 2024 hotel booking checklist here.
Subscribe to MWL!
Tmb packing list 2024, morocco packing list 2024, 2024 oahu bucket list.