Boston is the largest city in Massachusetts, boasting a bustling city life and rich history. It is beautiful, walkable and is thriving with arts, culture and theater.
Boston has so much to offer for travelers and locals alike.
Simply taking a long walk through its picturesque streets and lovely green spaces is the perfect way to spend a whole day.
1. Walk the Freedom Trail
The Freedom trail is made up of red bricks leading you around the city.
It starts at the Government Center, which is within walking distance of North Station.
This is free. Simply follow the red brick road and read about history as you go.
When you start at Government Center, be sure to check out the Holocaust memorial, which is also free.
It is a beautiful walkway dedicated to the victims of the Holocaust.
Look closely and see millions of numbers etched in the glass structures; these represent that forced tattoo numbers given to the victims.
There are six glass towers. This number represents the 6 million Jewish victims who died during this dark time in history.
They also represent the 6 candles on the menorah and the 6 main death camps in Nazi Germany at the time.
This is a powerful monument. Take your time and observe the details.
The Freedom Trail will take you to 16 historically relevant locations.
This is a great way to see the city while absorbing the unique history at the same time.More Info (click to expand)
2. Eat lobster and clam chowder
Clam chowder is a wonderfully rich soup made with fish, cream and spices. This is a staple of New England cuisine.
Notice how many restaurants and pubs offer this up on the menu. It is a comfort food perfected in this location.
Indulge and enjoy the textures and tastes.
Boston is also known for its wonderful lobster.
If you are from Europe, you may notice on menus that the best lobster comes from Maine.
Lucky for you, here in Boston it is much less expensive than in Europe and of course it is freshly caught!
“Lobstah on a Roll” is the place to eat an oversized lobster roll. The lobster roll is a beloved meal of locals.
Lobster is a sweet and delicate taste and when combined with mayonnaise and other spices, it is the perfect topping to large bread rolls.
You can also order a whole lobster and eat it this way.
t is messy and requires specific tools to get into each part of the lobster meat.
This method of eating lobster is available at the many seafood restaurants found in Boston.
I recommend trying both the chowder and lobster on your Boston getaway!More Info (click to expand)
3. View the city from the Prudential Center
The Prudential Center is a lovely building towering over the city.
You can see it in the distance from many locations around the city.
It is known for showcasing an incredible view from the top.
It is called the Skywalk observatory. Marvel at 360-degree views of this sprawling city.
Notice how unorganized the streets are unlike other major cities.
Boston developed as a city without true city planning.
You won’t see grids or an organized traffic system.
Rather, you will see winding streets, many one-way driving areas and a very unique perspective on the city.
This is the best view you can get.More Info (click to expand)
4. Tour Fenway Park
If you are in this neighborhood, I highly recommend checking out the Fenway area, which is where the famous Fenway Park is found. Tours of the historical park are available, should you choose to see where the beloved Red Sox call their home stadium.
This stadium has a special place in history. Built in 1912, it is the oldest stadium in the USA for the Major League.
In 1993, Fenway opened its doors for public tours.
Today it is one of the most popular destinations in Boston for tourists.
If you happen to be in Boston during the season you can try and buy tickets.
Seeing a game at Fenway is a unique and memorable experience.
The Bleacher Bar in the Fenway area is a watering hole where you can observe center field.
If you can’t score tickets to a game, this is the closest thing to being in the stadium.
Enjoy the energy and atmosphere of this lovely part of Boston.More Info (click to expand)
5. See a show in the Theater District
The artsy Boston Theater District dates back to 1793 when the first theater was built and opened.
The Red Coats occupied the city back in the Colonial days. Theater was a means of entertainment for the soldiers.
By 1900, this district boasted 31 theaters.
Movies that were shown changed depending on the times.
The Depression and the invention of the TV were two examples of the theater industry in Boston declining. Through the peaks and valleys of society, growth, technological advancements and the ever-shifting interests of the public, this fascinating district of Boston has seen it all.
Thanks to the University of Suffolk’s Modern Theater building project, a wonderful restoration took place for an old landmark.
The project focused on renovating the Modern Theater, using its original sign with a technologically savvy twist.
Found on Washington Street, this is now a 184-seat performance space.
Thanks to students at Suffolk sharing the space with their residence hall, the Theater District has been reinvigorated.
Take a stroll down history in this lively district.
There are always plenty of shows offered, should you decide to sit back, relax and enjoy the magic of performance.More Info (click to expand)
6. Eat in Little Italy
Did you know that the North End is built on landfill?
Set on a peninsula and facing the sea, the North End has undergone projects to extend this area further.
Settlers from all over Italy immigrated to this part of Boston.
As you wander through the streets, there are layers of Italian culture through the food, coffee shops and summer festivities.
The Patron Saints of the regions of Italy are celebrated in these festivals, preserving the heritage of the locals.
The North End is considered Boston’s first neighborhood. It has a much different vibe than the rest of Boston and it is separated from Boston city proper.
There is a positive sense of community in this neighborhood, which has attracted young professionals to find apartments here.
The location is a gateway to the whole city. You can easily access Boston from this wonderful location.
Copp’s Burying Ground is the second oldest cemetery in Boston, found right here in the North End.
Old North Church is Boston’s oldest church. It was built in the 1720’s and holds a special place in Boston history.
The high steeple is how Paul Revere was warned that the British were coming via the sea. Be sure to check out this church and cemetery while you explore the North End.
Eating in the North End is a must.
Whether you want to grab a wonderful sandwich or have a proper sit down meal, the food is authentic and delicious.
There is something for every budget and craving. Feel like you are wandering the streets of Italy in this authentic neighborhood!More Info (click to expand)
7. Check out South Boston
South Boston is nestled on the ocean and has a vast history.
You can hop on a bus from the downtown area, which will drop you off right in “Southie,” as the locals call this neighborhood.
Have you seen the movie “The Departed”?
Much of that film was set here in South Boston, where legends and stories of the Irish mob still live.
South Boston has been revamped over the years, as developers have taken advantage of its seaside location.
It is recommended to seek out the old Southie for a more unique experience.
The old school taverns and diners are mixed in with chic restaurants and pubs. You can surely spot the difference between the old and the new.
South Boston has a strong Irish-American heritage. At certain bars, you can hear the Irish accents of locals enjoying a pint.
L Street Tavern is a watering hole frequented by locals that has stood the test of time and gentrification.
Made famous by the movie “Good Will Hunting,” it had a small makeover, however it still has its local appeal. Enjoy the Boston accents and a lovely beer as you sit in this cozy space.
Boston Seaport is an area known for its thriving art culture.
Ever-changing art installations color this lovely area.
Simply walking around and enjoying the art and the vibe is a wonderful way to spend a few hours.
Lucky’s Lounge in the Seaport area is a fabulous place for a yummy meal or an old school cocktail.
If you are in the mood for some live music, check out their weekly live music offerings.More Info (click to expand)
8. Drink beer at one of the oldest pubs in the USA
The Green Dragon, found right in Boston’s historic area on Marshall Street, dates back to 1654.
Paul Revere and John Hancock frequented this pub.
In addition, the plans for the Lexington and Concord invasion could be overheard right here in this historic space.
These plans culminated in the famous ride of Paul Revere.
From Tuesday-Sunday, enjoy live music each night in this vibrant pub.
The Green Dragon offers a lunch and dinner menu and a large selection of drinks.
Although this pub marks a vital part of history, it has stayed relevant through the tests of time.
Boston has a rich history, but as a large college town, it caters to university students and young professionals.
This pub is a representation of Boston in its authenticity as a city.
As a college town and a town of great historic meaning, Boston intertwines a youthful spirit with an old soul.
See for yourself what The Green Dragon embodies for this unique city!More Info (click to expand)
9. Hop on a Duck Boat Tour
There is a reason why the Duck Boat Tours are such a favorite amongst tourists and locals.
Combining both land and water, the Duck Boat Tour offers history, beautiful views of the city and the opportunity to partake in a ride on an unusual piece of machinery.
Replicating the World War II amphibious DUKW vehicles, the Duck Tours navigate land and the nearby water, offering guests a combined tour experience.
The professional tour guides will take you through the history of Boston as you gaze out of the duck boat for spectacular city views.
The vibe is fun loving and playful, as you quack your way through the tour.
There are a few departure locations throughout the city, making it easy to hop on and enjoy!More Info (click to expand)
10. Check out the Skinny House
This rare gem located at 44 Hull Street in the North End is not mentioned in many travel guides, but it is a fascinating addition to your travels.
This narrow 4-story house is around 3 meters at its widest point and about 2 meters at its narrowest.
Despite its 4 levels, there are only 5 doors located in this house.
Built shortly after the American Civil War, the house was created out of spite in a family feud.
After their father died, two brothers inherited land.
One brother was off during his service in the military and the other brother took advantage of their inheritance by creating a large home.
The brother serving in the military returned home to a tiny piece of his inheritance, a piece so small his brother was confident he couldn’t build a home in such small quarters.
The narrow house was built anyway and it blocked the view and sunlight of his brother’s large home.
This is just one story of the legends surrounding the Skinny House.
We may never know for sure what happened here or why such a narrow home was created.
Enjoy this eclectic piece of history that is often overlooked by tourists and locals.More Info (click to expand)
11. Enjoy the 24-hour diner
The USA has a fabulous diner culture not to be missed on your trip.
An iconic symbol for American optimism, diners have a special place in the hearts of North Americans.
Commonly known as lunch cars in the 1920’s, they almost looked like motor homes in their exterior.
Many diners were narrow and small, allowing owners to pay smaller fees for land.
Some of the earliest diners were created out of converted rail cars, giving them an authentic appearance and dining experience.
Classic diners typically have siding made of stainless steel and a retro style interior.
South Street Diner is open 24-hours and boasts a delicious menu and great service. This is the ultimate people-watching destination, especially during the wee hours of the night.
South Street Diner attracts college students, business professionals, movie stars, late work employees grabbing a bite to eat after their shifts and rock bands needing to fuel up after a night of music.
The diner was built in 1947 for the purpose of supporting local factory workers.
Throughout time, the diner has become a Boston staple and a buzzing hot spot at all hours.
It has won various awards and was even featured in Rolling Stone Magazine.
You will have a memorable experience as well as a tasty American meal at South Street Diner.
No trip to Boston is complete without partaking in this all-night, energetic and enigmatic hot spot.More Info (click to expand)
12. Walk around Chinatown
Did you know that Chinatown in Boston is the only historical Chinatown in all of New England?
Built on top of landfill, Chinatown in the 1840’s was a less desirable place to settle, as there were many construction projects in the area.
The area therefore became an affordable place for immigrants to settle.
Chinese laundries started becoming popular around the 1870’s and the first restaurant in this area called Hong Far Low opened. As the need for construction grew, Chinese laborers were brought here in the 1880’s.
Fast forward to the 1950’s and Chinatown was booming.
Although the extensive construction projects in this area drove many families out of their homes, the population continued to increase.
Later in the 19th century, garment manufacturing became a staple of this area, thus creating Boston’s historic garment district.
Chinatown is the pulse of Asian-American life in New England. Around 70% of the population here is from an Asian background.
This culturally rich part of Boston hosts Asian festivals, restaurants and markets. It is a vibrant part of Boston, which also offers much in the way of residential life.
Local and regional transportation is available as well as two Chinese-owned bus companies, offering transport to the Chinese residents in this district.
Although this area is perfect for a stroll on your own, there are tours available for those of you looking for professional guides and/or more knowledge about the culture and history.More Info (click to expand)
13. Explore Cambridge
Boston is a university hub with more than 138,000 students residing in the city. Cambridge is home to the most prestigious institutions in both Boston and in the world.
Harvard has a stunning campus and lovely architecture.
The student-led tours of Harvard are award winning and informative, but if you feel like taking a stroll on your own, you won’t be disappointed by the USA’s oldest learning institution, which was founded in 1636.
The Massachusetts Institute of Technology is also found here in Cambridge. Ranked in the QS rankings as the world’s number 1 university for 2019-2020, MIT is worth exploring.
The campus is one of the most beautiful and technologically advanced in the USA.
On this campus you will find world-class architecture created by world famous architects from around the globe.
There is a buzz and energy found at university campuses; see for yourself what it feels like to walk around such a prestigious institution.
In addition to the universities, Cambridge is the home of some landmarks for you to admire on your adventure.
Harvard square is an incubator for ideas, knowledge and books. It has a rich history as a gathering spot for poets, teachers, booksellers, students, authors and creative types. Coffee houses, music, public art, yummy eateries and a variety of shops are all found here.
The first published American poet, Anne Bradstreet resided in Harvard Square.
In addition, the first printing press set up business here and this area of Boston was a place for authors to gather.
Harvard square was the first planned English-speaking town in North America.
The connections to early society are found in every corner here. As you walk the streets, take a deeper look, as many streets that were constructed in 1631 are still in use. You are literally walking on history!
Your mind has been nurtured thus far in Cambridge. Time to relax your sprit and move your body!
Grab a city bike or keep walking as you discover the Charles River Bike Path. The path is stunning with the river in view and luscious green surrounding you. This is also a convenient way to enjoy nature, as you are still in the city.
If you are interested in taking a deeper dive into Cambridge, its history and its famous landmarks, check out the Free Tours By Foot walking tour.More Info (click to expand)
14. Discover the history of Charlestown
This tiny piece of Boston is lovely, packed with history and easy to find.
Leaving the North End, simply take the Freedom Trail over the bridge and here you are!
Have you ever seen the movie “The Town”? This is filmed right here! Although this is a small area of the city, Charlestown’s waterfront location locked its role in Boston history.
Charlestown formerly had a “townie” vibe, however it is now home to many upper mobile young professionals. While this has changed its atmosphere, the locals are still around and there to greet you with a smile.
The Bunker Hill Monument was built as a way to commemorate the Battle of Bunker Hill, which was one of the first large scale battles between the British and Patriots during the American Revolutionary War.
Another reason to climb up and view this monument is the sprawling 360-degree city views of Boston!
There are plenty of green spaces as well, should you need a rest.
The USS Constitution is also a must-see in Charlestown. As the oldest commissioned warship still afloat in the world, “Old Ironsides” resides at the Charlestown Navy Yard.
Having defeated many British warships in the War of 1812, the boat received its nickname “Ironsides.” This was the result of British cannon shots bouncing off its iron exterior.
Now a National Park, the Charlestown Navy Yard is the home of this famous ship and greets countless visitors.
While Charlestown is noted for its historical monuments and lovely water front location, this area features underrated shopping.
Here you can admire vintage furniture, local artist shops and cute stores selling unique items.
The oldest tavern in Massachusetts called Warren Tavern is also found here!
Sip on a refreshing beer in the same place that Paul Revere and George Washington wet their whistles.
Enjoy their mouth-watering menu items as you take a break from sight seeing.More Info (click to expand)
15. Walk through Newbury Street
You are now entering the land of the 19th century brownstones!
This famous street is a tree-lined iconic place in Boston found in the Back Bay.
Its name derives from the Puritan victory in 1643.
The street was created during land filling in the 19th century and is one of the earliest roads.
By the 1920’s, Newbury Street became a hot spot for the upper class society, showcasing elegant clothing stores as well as formal dress and luxury goods.
The opening of the original Newbury Comics in the 1970’s boosted this street as a trendy shopping hub.
Throughout the 1970’s and 90’s, art galleries flourished as well as hip gallery hoppers. Its close proximity to the Berklee College of Music fosters a vibrant music scene.
In the early 2000’s, Virgin Records erected, creating more music buzz on Newbury Street.
Keep your eyes peeled for the lovely architecture and pop-up shops.
This sought after space in Boston is a fabulous location for pop-up stores, showcasing on trend retail spaces.
These are temporary, thus they are ever changing within the Newbury Street landscape.
Although this street is known for luxury and is considered one of the most expensive streets in the world, there is an eclectic mix of Bohemian stores as well.
Furthermore, Newbury Street offers restaurants, coffee shops and cafes to match your budget.More Info (click to expand)
16. Visit Boston Common
No trip to Boston is complete without visiting the oldest park in Boston and the oldest public park in the USA.
Conveniently located, Boston Common is adjacent to the main streets in Boston, thus providing the perfect place to take a lunch break, enjoy a peaceful walk or simply enjoy the scenery.
This 50-acre park was founded in 1634 and has been used for military training and executions.
After the Civil War, Boston Common developed into a tree-lined, lush park.
Although the park is not fenced in, it has an off-leash dog program for dogs. Expect to see furry friends roaming around free and off-leash!
The Frog Pond is where the magic happens here regardless of the season.
In the summer, your kids can enjoy a spray pool to cool off as well as a carousel sure to provide jovial entertainment!
June-August features free yoga at the pond, should you be visiting at this time and feeling as though you need a workout on your trip.
Indulge at the Frog Pond Café for yummy drinks, snacks and meals.
There are also various food trucks parking here; you have the luxury of choice when it comes to your lunch or dinner in Boston Common.
Berklee College of Music students offer free lunch time piano performances, adding a special treat to your time here.
If you are visiting during the winter months, brush up your skating skills, as the Frog Pond turns into an ice skating rink!
Not far from Boston Common is the Boston Public Garden, America’s first botanical garden.
Marvel at untold stories of the Public Garden as you glide on swan boats. The free 60-minute tour is fascinating and fun.
Nearby is Beacon Hill, which is a maze of tiny, stunning streets lined with brownstones and trees. Get lost in history and beauty in this area of Boston.More Info (click to expand)
17. Check out the Free museums
Boston is bursting with museums in every field and area you can imagine.
What you may not know is that there are plenty of fantastic museums you can visit that are free or offer admission for a very affordable price.
The USS Constitution, which was mentioned earlier. The museum of the historic ship is completely free.
Looking for a museum that is kid friendly, interactive and affordable?
Check out the Boston Children’s Museum. Although there isn’t free admission everyday, on Friday nights from 5-9pm, you can purchase a ticket for $1. What could be more magical for your kids than going to a child-centered museum at night?
Boston was home to one of the first metropolitan water systems. Learn all about this fascinating history at the Waterworks Museum. Enjoy the array of exhibitions for free Wednesday-Sunday.
Boston University Art Galleries is great for those of you seeking a creative outlet. This museum offers different galleries during the course of the year free of charge. The hours for the galleries are in line with the Boston University calendar and have limited time frames over the summer. The availability is Tuesday-Sunday.
History buffs look no further than the Bunker Hill Museum. Free entrance and a dose of Boston history are provided for guests. The museum focuses on the history of the United States through displays and exhibitions. The Bunker Hill Museum is open daily from 10am-5pm.
The Boston Fire Museum is a museum most likely overlooked by tourists and locals. It has a collection of some of the oldest devices used in fire fighting. There are also fire engines housed here dating back as far as 1793. This is an especially great place for children, as most kids love firefighters. Note that the Boston Fire Museum is only open on Friday and Saturday from 5-8pm.
Curious about the history of medicine in the USA? The Warren Anatomical Museum showcases over 15,000 artifacts all relating to the history of medicine. Some of these fascinating pieces are from as far back as 1810. This museum is open from 9am-5pm Monday-Friday.More Info (click to expand)
18. Walk the Greenway
The Greenway is a modern park carving through Boston.
The best way to describe this space is an urban oasis in the middle of the city. It is beautiful and cleverly designed as well.
It was created after the famous “Big Dig” project, as the tunnel system created below the city left space for new projects.
Connecting Boston’s most vibrant and oldest neighborhoods as well as the waterfront, the Greenway is a place to gather, foster community and take a break from the concrete jungle.
This green space is so much more than a place to relax and enjoy a nice stroll.
There is a public art program, which has made the Greenway a premier destination for showcasing public works of art in the city.
The exhibitions are free, thought provoking and temporary.
Artists have a fantastic opportunity to contribute their work to this innovative space. There are many different exhibits for your viewing pleasure.
Let’s not forget food!
Food trucks are a staple here and offer international treats like tacos and curry.
There are also beer and wine gardens where you can sit outside and enjoy yummy beverages while taking in the sights and sounds of the Greenway.
The Greenway Carousel is a great way to connect with your inner child. Another way for you to have fun and play in the summer months is with the 7 water attractions on offer.
You won’t find any chemicals in the plants and landscapes here!
This is one of the few public parks in the region that is fully managed organically.
With sustainability and healthy ecosystems at the forefront of the plants and landscapes here, the Greenway prides itself on not causing harm to the environment.
There is even the Greenway Beehives! This is an area fenced off from the public where Italian honeybees live and spread pollen to keep the flowers looking beautiful.
Fusing beauty with a social conscious, the Armenian Heritage Park on the Greenway is a celebration of immigration.
The design engages visitors to join together on common ground, commemorating the immigrant experience.More Info (click to expand)
19. Listen to authentic Irish music
Although cities all over the globe are packed with Irish pubs, Boston has the unique advantage of having a strong and rich Irish history.
Boston has 100’s of Irish pubs at your disposal.
Visiting one of the many establishments is not only a great time, but it embodies a piece of Bostonian history.
A great way to spend an evening in Boston is to cozy up at one of the many Irish pubs here, order some delightful comfort food and listen to authentic Irish music.
As there are so many, to choose from, I have narrowed down suggestions during your stay.
The Black Rose offers music 7 nights a week and has been running for 40 years. Enjoy the classic atmosphere and feel good vibe right in Faneuil Hall.
Emmets Irish Pub and Restaurant found in Beacon Hill is considered one of the most authentic Irish pubs in Boston. Serving traditional Irish fare in a lovely atmosphere, you will leave full and happy.
The Burren is an Irish pub founded by Irish musicians. Located in vibrant Somerville, this pub takes you back in time with its vibe and music. Expect some spectacular Irish music sessions here!
The Druid, located in Cambridge, is housed in the oldest wooden mercantile building in Cambridge. The atmosphere is hard to describe, therefore you must go see this gem for yourself! Traditional Irish music sessions are hosted on Saturdays and Sundays.
Flann O’Briens on Mission hill boasts a stellar Irish breakfast, should you need a mouth-watering meal to fuel your day. Although this is not a place to see live music, it is an Irish pub noted for its authentic Irish breakfast.
Found in the chic South End of Boston, J. J. Foley’s has been operating for 100 years and is the oldest family run Irish pub in town. This is also not offering live music, however it deserves to be on this list for its long-standing mark in Boston history.
Mr. Dooley’s Tavern is a fabulous watering hole located in the heart of the financial district. The relaxed attitude is refreshing and calming. Live music is offered 7 nights a week, promoting bands from Boston and Ireland. Although there is scheduled music, there is always a chance that a “Sessuin” may start up at any moment, adding to the authentic Irish pub feeling.More Info (click to expand)
20. Eat Boston Cream Pie
The official dessert of Massachusetts is the Boston Cream Pie.
Don’t take my word for it; try this delectable treat for yourself.
There are lovely flavors all combined in this decadent dessert.
Traditionally it is a yellow cake filled with custard or cream and then topped with chocolate glaze. It will melt in your mouth.
During the 1800’s, Bostonians enjoyed a dessert called the “American pudding-cake pie.” At the Omni Parker House, which was formerly known as Boston’s Parker House, this was a dessert served to guests.
The first chocolate mill opened in a suburb of Boston called Dorchester, thus Boston had plenty of access to chocolate.
The Parker House’s chef Anezin at the time decided to try a little experiment with the beloved cream pie. He drizzled chocolate icing onto the sponge cake that was filled with custard.
It was formerly called the “Parker House Chocolate Cream Pie” and was later renamed the “Boston Cream Pie.”
Although many bakeries and hotels will offer this slice of Bostonian history on a plate, if you are interested in tasting this classic treat where it all started, head over to the Omni Parker House and see what all the fuss is about! Maybe this will become one of your favorite desserts.More Info (click to expand)
What are your thoughts about Boston? Do you have any questions or anything cool still to add on? We love to discuss travel so go ahead and fire away, there are no wrong comments!
Also, please let us know how your trip went and what was the most exciting part about it.