We all know the U.S. isn’t old by geopolitical standards. All our European friends will laugh at our meager almost-250-year history! What history we do have mostly kicked off here, in New England – Boston being one of the major players on the road to independence.

There are a whole lot of things to do in Boston – a lot of which involve learning about the lead up to the American Revolution. Yes, this is (obviously) the place where the Boston Tea Party happened. Landmarks, iconic old buildings and a ton of museums are the usual order of the day in this famous city.

That’s the easy way to do it though. For something more off the beaten track, you’ll want some more unique things to do in Boston. And we’re here to help! Sit back, get comfy, and enjoy our list of the top things to do in Boston. We’ve done the hard work so you don’t have to, letting you find the more leftfield, local and cool spots dotted around the city.

Top Things to Do in Boston

1. Walk Boston’s Freedom Trails

Freedom Trails Walk

Probably one of the most popular things to do in Boston, the Freedom Trails are a way to learn about the history of the city.

Why “freedom”? Because Boston was basically the birthplace for the independence of the United States of America, back then a British colony. The Freedom Trail is an iconic way to discover this history of freedom.

Walk from Boston Common (the first public park in America, we’ll have you know!), past the Granary Burying Ground, which dates back to the 1630s, and pause for a moment of reflection at the site of the Boston Massacre outside the old statehouse. Don’t worry: this urban walking trail is easy to follow and takes about 90 mins to walk.

2. Relive the Boston Tea Party

Relive the Boston Tea Party
Photo: Lee Wright (Flickr)

The entire US East Coast is integral to the history of the great nation. A key part of America’s foray into independence was, of course, the Boston Tea Party. We’d tell you all about it, but… We think the Boston Tea Party Museum would probably be a better place for that.

An essential thing to do in Boston, it’s not just any old museum – this one’s actually mainly housed on an old ship (well, a replica of an 18th-century ship). Here you can learn all about that fateful day, 16th December 1773, the whole “no taxation without representation” thing, and the lead up to the American Revolution. You can even pour tea into the sea as an eternal !#*$ you to Britain.

Back Bay, Boston

Back Bay

Need a hostel in Boston? If you’re visiting Boston for the first time, there’s no better neighborhood than Back Bay. Centrally located and well connected, Back Bay is close to everything.

Places to visit:
  • Marvel at the world-famous, three-story stained-glass globe at The Mapparium
  • Browse the shops, bar and restaurants that line bustling Boylston Street
  • Watch the game and drink a few pints at The Pour House Bar and Grill

 For more Places to Stay, check out our full Boston Neighborhood Guide!

3. Experience the sights and sounds of Chinatown

Chinatown Boston

Like all good, big American cities, Boston has its very own Chinatown. And this one is the only major Chinatown left in the New England area. Dating back to the 1870s, when Chinese laborers from San Francisco to break a strike, the Chinatown has boomed instead of falling into decline like other Chinatowns in the region. It’s the city’s centre of Asian American culture with a TON of Chinese and Vietnamese restaurants to try out.

Come for the amazing Chinese food (particularly Fujianese cuisine), stay for the buzzy atmosphere after dark. Get off at the Chinatown stop on the MBTA Orange Line. Exploring this is one of the more unique things to do in Boston: especially during Chinese New Year!

4. Get schooled at Harvard

Get schooled at Harvard

Harvard University is one of the most famous universities in the world. Luckily for you, it’s in Boston and it’s not exactly closed off to the public. You can just… stroll around. Which makes for one of the more unique things to do in Boston, we’d say.

The Harvard Yard, for example, is one of the oldest parts of the university. It’s here where you’ll find a load of cool buildings, like Massachusetts Hall which dates back to 1720. You’ll even be able to spot the statue of the founder of the university, English clergyman John Harvard himself. There are a ton of old stories about the university, so (if you can) we’d recommend some sort of guide. Or read up beforehand.

5. Take a stroll around Boston Public Garden

Boston Public Garden

Back in Boston’s Financial District, if you’re feeling up for an outdoorsy thing to do in Boston, we’d say head on down to Boston Public Garden. Established back in 1837, this 24-acre green space has a fair few interesting sights and a lot of history, but the paths, flowerbeds and statues make it a picturesque place.

Some of that historical statue action includes George Washington, so make sure you get your best selfie face on – or do it the old school way and get a passerby to take a photo of you and the big man himself. Afterwards, head to the boating pond, complete with vintage swan boats made in 1877 (don’t worry, they still float).

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6. Shop for souvenirs at Quincy Market

Quincy Market

You’re in Boston. You don’t want to get souvenirs to take back home from some random little tourist shop, right? Of course you don’t. You want to get them from somewhere authentic.

For that, we’d head to Quincy Market – one of those unmissable things to do in Boston.

Why unmissable? Because it’s one of the largest markets in the US! There’s loads of stuff going on here, from interesting trinkets to those all-important souvenirs. And if you’re prone to getting hangry, don’t you worry: this is a prime lunchtime spot with a ton of vendors and food stalls to keep you well fuelled for your market meanderings.

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7. Have your fill of the tastiest food in town

Bostons North End

Speaking of food, Boston is pretty dang famous for its food. You would be doing the city a SERIOUS disservice if you weren’t to try out any of its top dishes.

Start off in Boston’s North End and eat your way south as you discover the city’s roots through your tastebuds. There’s plenty of Italian-American stuff, from fresh cannolis to pizza sandwiches. They’ve got a fair bit of seafood here too, being positioned on the New England coast: we’re talking clam chowder, oysters and the famous lobster rolls. You’ll even find baked beans and fish ‘n’ chips (hello Britain).

It’s a mountain of delights, making for one of the more non-touristy things to do in Boston. Tip: Leave room for Boston cream pie! If you have time, you could even take one of the many fantastic food tours in Boston!

8. Pretend you’re in a movie

L Tavern Street, Boston

Film buffs and movie nerds: listen up. Boston, being the iconic, historic city that it is, is naturally a pretty desirable filming location. Movies and TV shows galore have had the streets of this storied city as a backdrop.

For starters, a drink at the L Street Tavern (as seen in Good Will Hunting) is in order. Then you peep a lot of sights from Ally McBeal and Legally Blonde as well as The Departed. Head to Beacon Street Bridge for scenes from The Social Network and Whittenton Mills Complex to see bits from Shutter Island.

There’s LOADS more. You either know already, or you do some hefty research. Either way: it’s one of THE best things to do in Boston.

9. Take a trip to the iconic New England towns

New England towns

Boston is one of the major cities of the beautiful area that is New England. This region is known for its rugged coastline, endless suburbs and picturesque fishing villages. Exploring it using Boston as a base is very, very doable.

So we’re saying it’s one of the best day trips from Boston you could ever do. Especially if you like your destinations to be extra charming and historic. There’s Sandwich, for example, which is the oldest town in New England, dating back to 1637 – expect lots of old buildings (including a 1698 tavern!). Plymouth, where the United States basically was born, is well worth a visit. Cape Cod is also awesome. This whole region is awesome, actually. Definitely go.

10. See the home of the Boston Red Sox

Fenway Park

Even if you don’t know much about baseball at all, chances are you know the names of a few of the most famous teams. The Boston Red Sox will be one of those teams.

Dating back to 1906, it’s a pretty historic team with an iconic stadium: Fenway Park, one of America’s most well-loved ballparks. If you want to get into the proper details of how it all works, and with some history, you can visit the park itself on a guided tour. That’s cool. But to get the full experience, a game is highly recommended. One of the most essential things you could ever do in Boston. We’re 100% serious.

Unusual Things to Do in Boston

11. Get spooky in Salem


If you feel like getting out of the city and its skyscrapers for a minute, then for a great day trip from Boston we’d recommend heading out to Salem. Not just the name of Sabrina the Teenage Witch’s cat, Salem is an infamous village that was known for its pretty bad witch trials from 1692 to 1693. Learn all about it at the Salem Witch Museum, complete with exhibits and info as to why all that madness was going on.

For something that looks right out of a classic American horror film, visit the House of Seven Gables and the Witch House at Salem. When you’ve had enough of scaring the bejeezus out of yourself, head back to the noise of the city. Ahh – that’s better!

12. See the world at the Mapparium

Photo: Smart Destinations (Flickr)

You might be thinking, “What is a mapparium and why should I be going to one?” It’s a glass globe, but it’s more impressive than it sounds. One of the more unusual things to do in Boston, this thing really is huge. Spanning three stories and intersected by a glass staircase, the globe is made up of different panels that make up, you guessed it, the map of the world.

It’s an interesting way to see what is essentially… a map.

It’s pretty weird though because it’s from 1935 and all the country boundaries are wrong: think African colonies and the USSR. But what makes it even more of a weird thing to do is, being a perfect sphere, the echoes of people speaking are pretty wavy.

13. Discover the secret of Bodega

Secret of Bodega
Photo: Tom Rose (Flickr)

What is the secret of Bodega? Wouldn’t you like to know! … Ah, we feel bad. We’ll tell you. It’s one of the more unique things to do and that’s because it’s a super high-end streetwear store hidden in plain sight. Well, actually just hidden at the back of an everyday-looking bodega.

The bodega itself looks normal enough: shelves of household products and food. But at the back of the store, there’s a Snapple machine (stay with us) which actually doubles up as the door to the fashion shop itself. It’s all very sleek and cool and all the more interesting because finding it is like playing a real-life escape-the-room game.

Safety in Boston

The capital of Massachusetts, with its universities and student population, is generally a pretty safe city. Being a tourist you’re unlikely to encounter any serious crime anyway – most of it happens in outlying, inner-city neighbourhoods.

Of course, that doesn’t mean there’s no crime. As with most cities on Earth, keeping track of your belongings at night and especially in crowds around touristed areas is a smart idea. Pickpockets and thieves do exist.

But a good way to stop would-be pickpockets in their tracks is simply to wear a money belt (which we highly recommend); something like the very discreet Pacsafe Money Belt will work wonders.

It’s probably not a great idea to go wandering around secluded areas, like public parks, at night time. We would advise sticking to busier, well-lit areas after dark. It’s a common-sense thing, really.

That’s basically it. Just note that it can get pretty cold in Boston. If you’re arriving in winter, you’ll definitely want a scarf, hat, gloves – the whole shebang! Read our tips for traveling safely before you fly and always get travel insurance. Check out our roundup of the best travel insurance.

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Things to Do in Boston at Night

14. Have fun on a pub crawl

Historic Pub Crawl
Photo: Ben+Sam (Flickr)

With all that colonial and European heritage going on here, there are a ton of pubs in Boston. Like, we really mean a lot. Not so much British boozers either, but there are a fair few Irish pubs here. When the Irish immigrated to Boston it seems they brought their pubs with them and we’re fine with that.

The pubs in the Faneuil area of the Historic Downtown of Boston are where it’s at. Here you’ll find pubs like the mentally old Green Dragon Tavern (1654), The Bell In Hand Tavern (1795), and the Warren Tavern (1780). Basically, drinking your way around these pubs is one of the best things to do in Boston at night. No doubt about it.

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15. See a show at the historic Boch Center-Wang Theatre

Boch Center-Wang Theatre
Photo: Ksaziz (WikiCommons)

Originally opened in 1925, the Wang Theatre is pretty much an institution of Boston. Going there, even just to see the outside of it, is cool enough. But for one of the more cultured things to do in Boston at night, we’d highly recommend getting yourself a ticket to see one of the nightly performances at this storied venue.

The lobby interior is super stunning, complete with chandeliers and so much gilded gold-leafing that it almost feels like a palace. The theatre itself is beautiful. Basically, if you’re at all interested in musicals (and honestly, even if you’re not) you should experience this place. Get there early before the performance starts just to gawp at how cool the auditorium is. Definitely one of the cooler, more non-touristy things to do in Boston.

16. Watch a cool movie at Coolidge Corner

Coolidge Corner
Photo: Mad Ball (Flickr)

Looking for something to do in Boston at night that doesn’t necessarily involve drinking (and that isn’t a musical)? Well, you’ve come to the right place. Not only is Coolidge Corner a cool retro building dating back to the 1930s, but it puts on an awesome after dark movie series called Coolidge After Midnite (we especially like the spelling of “midnite”).

Every Friday and Saturday night the theatre shows everything from ’50s classics and cheesy ’90s movies to horror staples (eep!) and even cult 8mm films. And just about everything in between. In true Boston fashion, there are stodgy snacks and cinema favorites to gorge on.

Where to Stay in Boston

Looking for a specific place to stay? These are our highest recommendations for places to stay in Boston.

Best Hostel in Boston: HI Boston

Located in Downtown Boston, the HI Boston is the best hostel in the city. It is close to restaurants, shops, bars and clubs. Public transit is nearby and it is a short walk to the city’s top landmarks. This hostel has private rooms and bathrooms, and a common room with a pool table, TV and laundry facilities.

Best Airbnb in Boston: Studio in Prime Location

Spack dab in the heart of Back bay is this astonishing home that offers one of the most comfortable stays in the city. It’s definitely one of Boston’s best Airbnbs. On the lively street of Newberry, you have access to the most premier shopping in the city and the award-winning restaurants you’ve only seen on tv. Speaking of food, the kitchen is small but does have everything you need to cook a quick meal, but being in the popping neighborhood, you will most likely be enjoying all the cafes he neighborhood has to offer anyways.

Best Hotel in Boston: Hyatt Regency Boston

Our pick for the best hotel is the Hyatt Regency. Located in Chinatown, this four-star hotel boasts an incredible pool, an in-house restaurant and a stylish lounge bar. It has 502 modern and spacious rooms and a relaxing sauna. The Hyatt Regency is conveniently located for exploring Boston’s best neighbourhoods.

Check out Airbnbs in Massachusetts for even more Boston accommodation inspo.

Romantic Things to Do in Boston

17. Sip champagne on a yacht

Northern Lights

Champagne – check. Historic yacht – check. So, yep, it’s pretty much all aboard on this one for (possibly) the most romantic thing to do in Boston.

There are a number of boat-plus-drinking things you can do in the city, but our favourite one is the very cool 1920s commuter yacht, the Northern Lights, that departs from Rose Wharf. This boat is super cool and isn’t just one-on-one-on-one with you, your partner and the captain (awkward). It has a full crew and candlelit tables for full romantic ambience of other people clinking glasses and murmuring sweet nothings.

Gaze upon the city skyline and pat yourself on the back for booking such an awesome night for your S.O.

18. Wander around Beacon Hill

Beacon Hill

One of the most picturesque neighbourhoods of Boston, Beacon Hill is an amazing place to explore. Especially hand-in-hand with your other half. Another option is to explore the area with a local guide and get to know more about the historic charm.

Strolling the especially charming Acorn Street, with its cobblestones, rows of red-brick, overflowing flower boxes and gas lamps – or admiring the houses on Louiseburg Square – has got to be one of the best things to do for enamored couples. You’ll find yourself saying those stupid things like I’d love to live here: it’s one of the most desirable (and expensive) areas of the city. Good luck with that. Seriously though, this area is insanely beautiful and a highlight of our Boston Itinerary.

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19.  Browse the books (but be quiet) at Boston Public Library

Boston Public Library

If you like books, this is going to be one of THE best things to do in Boston. Period. It’s one of the largest libraries in the United States, with over 22 million books. 22 million! Just think how many words that would be. Insane.

Founded in 1848, it’s a beautiful building with murals, chandeliers and a reading room that’s to die for (well, almost): it’s got beautiful dark wood desks complete with those iconic green library lamps. If you can be discreet about it without annoying people, it’s probably one of the best Instagram spots in Boston. If you actually want to learn stuff, there’s a regular program of free talks and lectures that goes on here. Either way, exploring this place is one of the best free things to do in Boston.

20. Watch Shakespeare for free on Boston Common

Boston Common

For another very cool free thing to do in Boston, we’d recommend heading over to Boston Common on given day of the week (except Monday) from April till November. This is an idyllic summertime activity in Boston. Here’s where you’ll get the chance to catch a spot of Shakespeare, performed by many different companies in the park’s historic Parkman Bandstand.

What better thing to in Boston than watch A Midsummer Night’s Dream on a summer’s evening in the city’s oldest park – all for free! A very cool idea. You can make a reservation for a chair ($5) up to 5 hours before the performance starts. Otherwise, get a picnic blanket and snacks and claim a spot.

21. Visit the oldest bookshop in the USA

Brattle Book Shop
Photo: Olivier Bruchez (Flickr)

More free stuff to do in Boston for bookworms now as we whisk you to Brattle Book Shop. This family-owned bookstore is a veritable Aladdin’s cave of used books and, like many things in Boston, is the oldest one of its kind in all of America.

Partly inside, and partly located down an alley next door, there are so many books to sift through here that – if you really are a book fan – you could definitely spend a whole afternoon here. The shelves are completely stuffed with books. We reckon it’s easily one of the best things to do in downtown Boston. Very cool.

Top tip: Head to the top floor for rare first editions.

Books to Read in Boston

Here are some of my favorite books books to read in USA:

Walden – This transcendental masterpiece by Henry David Thoreau helped modern Americans rediscover nature and her beauty. Written outside of Boston at Walden Pond.

Mystic River – A murder shakes a traditional Bostonian family and causes the whole neighborhood to be turned upside down. It inspired the award-winning film of the same name.

Infinite Jest – An important novels of the 21st century (so far) explores the current nature of the American Dream through the antics of a screwed-up family. Equally funny as it is revelatory.

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    Best Things to Do in Boston with Kids

    22. Get your geek on at The Museum of Science

    The Museum of Science

    If you’re in the city with your family and you’re looking for the best things to do in Boston with kids, well, here’s one of them. The Museum of Science is a very cool place for you to explore. And, what’s more, if you get caught out with some inclement weather, it’s all good since it’s indoors (automatically one of the best things to do in Boston when it rains).

    Get spacey at Moons: World of Mystery, where you can journey through the solar system, or hit up the dinosaurs exhibit for those with 8-year-olds with an obsession with toothed and clawed prehistoric reptiles. Basically it’s loads of fun – and it’s got a cafe if you forget to bring those all-important snacks.

    23. Go whale-watching

    Go whale-watching

    Honestly, what could be more memorable than whale-watching? It’s incredible to see these huge marine mammals up close and personal, so if you’ve got older kids who can sit still for a while (or are entertained enough by being on a boat): go whale-watching!

    There are many different ways to do it, some of which involve simply looking really, really hard from the coastline itself, but the best way to spot the whales is to get you and your family on a boat to see them much closer. We’re talking humpbacks, finbacks and even white sided dolphins. A lot of the boats come complete with guides and experts who’ll be able to answer any questions on these amazing animals and their habitat.

    Other Unmissable Things to Do in Boston

    24. Have a few drinks in a local Boston brewery

    Local Boston brewery
    Or just inhale ALL the hops, like this guy.

    Boston may be famous for its many, many pubs. But in some ways, that’s old news. We mean, literally: that’s olden-days stuff, right? If you’re interested in knowing what’s going on in present-day Boston, you should get yourself to a craft brewery.

    At Nightshift Brewing you can get a taste of craft beers that have been made using habanero peppers and peppercorns in the brewing process (not as bad as it sounds), at Mystic Brewery you can sample French farmhouse-style ale, whilst at Down The Road Beer Co. they offer up a wide selection of differently brewed beers. Definitely one of the more hip things to do with your time in Boston.

    25. Enter a new world at the Class of 1959 Chapel

    If you were thinking Boston was all old buildings and you were hoping your Instagram feed could get some of that mid-century modern stuff that you really, really crave, don’t worry. We’ve got the goods.

    Case in point: the Class of 1959 Chapel. Located on the Harvard Campus but honestly nothing like the red-brick buildings of the famous university, this chapel is an architectural gem. It’s all glass and concrete and is overflowing with houseplants. It’s a chapel with a difference, creating a space away from the busy city to reflect – complete with sunken water garden and pyramid. Easily one of the best things to do in Boston by yourself. Well, just you… and your camera.

    No sneak peeks! But you can read about it here.

    26. Find the best Boston pizza in town

    Best Boston pizza

    Like pizza? No? Well, skip this one (and don’t talk to us again). If you do like pizza then read on, dear friends. It’s claimed variously that Boston is home to the best pizza in the whole damn USA. To be fair there is sizeable Italian community in Boston, so it doesn’t exactly come as a surprise.

    For one of the very best places to get pizza, head to Regina Pizzeria. Dating back to 1926 this awesome place still serves up slices to endless cues of hungry visitors. Another place is Santarpio’s, an old bakery turned pizzeria that does some amazing things with dough and tomato sauce. The 1960s Galleria Umberto is another over-the-counter favourite. Basically, getting your pizza on is one of the best foodie activities in Boston. 100%.

    27. See an old operating theatre

    Ether Dome
    Photo: M. Rogawski (WikiCommons)

    For one of the more… unusual things to do in Boston, we’re recommending a former operating theatre. Yes, you read right. It’s not weird, spooky, or housed in a derelict old building though. Located at the Massachusetts General Hospital, it’s called the Ether Dome and is one of those old-school theatres with the seats and a big glass dome in the roof. It’s free.

    It was a working operating theatre from 1821 to 1868 and is allegedly the place where the first demonstration of surgical anaesthesia as given (the guy they used it on apparently woke up and said he felt no pain). Weirdest thing: There’s now an Ancient Egyptian mummy here. Don’t ask us why, there just is. Deal with it.

    28. Take in the city from above

    Skywalk Observatory
    Watch that beautiful city glimmer!

    The tallest (and only) observatory in Boston, and the tallest in all of New England, the Skywalk Observatory isn’t a standalone building: it’s located on the 50th floor of the 228 metre tall Prudential Tower.

    Take yourself to this business-oriented building and ride the elevator to the 50th floor for some pretty amazing sights across the city. There’s also a restaurant on the 52nd floor for even better views if you’ve got the money for dinner there. With its 360 degree views and even an audio tour, seeing the skyline from above has got to be one of the coolest things to do in Boston. Warning: it’s not cheap.

    29. Spend the day eating in Maine

    Eat in Maine

    The rocky New England coastline is famed for its seafood so for one of the best day trips from Boston, take yourself on a little excursion to the neighbouring state of Maine. The food here is pretty amazing, making for another amazing trip for foodies.

    Maine accounts for about 90% of the United States’ lobster supply, almost all blueberries produced in the USA, and about 500,000 gallons of maple syrup. There’s dishes that involve clams, oysters, and a whole bunch of fish. For something truly tasty, the brewpub of Federal Jack’s serves up amazing food, often involving famed Maine potatoes. And for something homely, go on the hunt for a bean supper!

    30. Find out what a ‘Smoot’ is at Harvard Bridge

    Smoot Harvard Bridge
    Photo: Beyond My Ken (WikiCommons)

    A smoot, you say? We’re glad you asked. In 1958 a group of pranksters from MIT’s Lambda Chi fraternity took a freshman pledge in the form of Oliver R. Smoot to Harvard Bridge. They had him lay down at the start of the bridge, made a mark where his head was, then had him lay down again and repeated the process.  In this way, they measured the whole of the bridge in ‘smoots’ (5 foot 7 inches, in case you were wondering). The whole thing added up to 364.4 smoots and 1 ear.

    Oh the hilarity of fraternities. Anyway, visiting this landmark is one of the more unusual things to do in Boston and a must if you’re a fan of kooky measurements. Who isn’t?

    31. Walk down All Saints Way

    All Saints Way
    Photo: Anna Hanks (Flickr)

    For another unique thing to do in Boston, take yourself to All Saints Way. This interesting alleyway is basically a shrine to almost every single Catholic saint going and is the life work of Peter Baldassari. He decorates the place with seasonal decorations and a whole truckload of religious iconography.

    Sometimes it’s open, sometimes it’s closed. But even when it is closed, just seeing the entrance and the gateway with all its decorations is pretty impressive. If you’re lucky, the owner himself might give you a tour and tell you all about his creation. An amazing off-the-beaten-track thing to do in Boston, one that draws a steady drip of curious visitors, you’ll find this one in Battery Street in Boston’s North End.

    Day Trips from Boston

    Want to get out of the city? Visit one of these places near Boston for a chance to stretch your legs and experience some of New England’s best scenery.

    Cape Cod

    Cape Cod Boston

    The iconic Cape is Boston’s idea of a vacation. Famous for its endless beaches, charming towns, and historic lighthouses, Cape Cod has become the poster child for the New England coast. Lots of people travel to the Cape in the summer and spend an extended period of time here, either for work or play.


    Salem Boston

    This historical town was made famous by its gruesome Witch Trials. Anyone who has had any interest in New England history, or the occult for that matter, end up visiting this town. Contrary to its grim reputation, Salem is actually a fairly affluent place these days.

    Portland, Maine

    Portland Maine

    The charmingly unassuming Portland, Maine is a mere 2-hour drive away from Boston and makes for a great road trip. Spend the day exploring the rugged coastline between Massachusetts and Maine, hitting up as many beaches as you can. Arrive in Portland and then grab a fresh lobster at the Old Port with a nice hearty beer.

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    3 Day  Boston Itinerary

    The following is a sample 3-day itinerary for touring Boston. Most of the top destinations that were already mentioned in this Boston travel guide are covered in this section. 

    map of boston travel guide
    Locations are: 1. Fenway 2. Back Bay 3. Copley Square 4. Boston Commons 5. Beacon Hill 6. North End 7. Long Wharf 8. Chinatown/Leather District 9. South End 10. Dorchester 11. South Boston 12. South Boston Waterfront 13. Logan International 14. East Boston 15. Charlestown 16. MIT 17. Central Square 18. Harvard 19. Allston 20. Green Necklace. Map of Boston not to scale. 

    Day 1: Downtown Boston

    On the first day of our Boston travel guide, we’re going to spend the entire day walking from Fenway to North End. Along the way, we’re going to hit up all of the most eminent points of interest in Boston including, but not limited to, the Boston Commons and Quincy Market.

    Make sure you have a comfortable pair of shoes because it’s going to be a long day!

    Start by catching the T at Fenway Park, which is one of the most famous stadiums in the USA. (Bostonians treat it like a church.) Baseball rallies are held here regularly and most of the bars are packed, regardless if there’s a game in progress or not.

    Let’s depart from Fenway and head deeper into Downtown. Cross the Back Bay Fens and Fenway Garden Society and head for Boylston Street, which is one of the city’s main roadways.

    Walk about 20 minutes through the Back Bay district until you reach one of my favorite spots: Copley Square.

    This square hosts some of the most arresting buildings in Boston, including the Public Library, Trinity Church, and John Hancock Tower, all of which create a wonderful juxtaposition.

    Continue walking east and soon you’ll arrive at the Boston Commons – the largest and most important park in the city. The Commons is a very popular place to hang out in, no matter what time of the year. Going for a swan boat ride is somewhat customary in the Commons, if not a little touristy.

    Just north of the Commons is Beacon Hill, which is one of the most historically significant areas in Boston. Lined with brownstones, paved with cobblestones, and topped by the magnificent State House, Beacon Hill is like a time capsule from Colonial days.

    Let’s wrap up our day and make a beeline for North End for dinner. The North End is the old Italian quarter and is one of the coolest places to eat in Boston. Here, the pasta is piled high, the meatballs are fat, and the bakeries are just about endless. Thanks, Italy.

    downtown boston travel guide

    Day 2: Visiting Cambridge

    Though not technically a part of Boston, nearby Cambridge is still totally worth checking out thanks to its prestigious institutions. Most notably, Cambridge hosts two of the most important colleges in the world – Harvard and MIT.

    Let’s begin the second day of our Boston travel guide at Harvard.

    If you grabbed the T, the first place that you’ll see on campus is Harvard Yard. The Yard is the oldest part of the campus and has been the setting for many films. The Yard is a bucolic setting and will probably be overrun by scampering students.

    As you wander around the campus, you’ll notice that the architecture of Harvard is a gorgeous blend of several styles – Gothic, Classical, Revival – yet every building is still made from that quintessential red brick. Several of these buildings host noteworthy museums and most are open to the public. For me, a tour of the campus is reason enough to visit Cambridge.

    Let’s depart Harvard and visit a very different college: MIT (Massachusetts Institute of Technology). MIT is very different from Harvard, in both essence and appearance.

    Whereas Harvard excels in the arts and business, MIT is all about engineering and the sciences. MIT’s most notable building is the Great Dome – a fine example of neoclassicism. Aside from this triumphant building, there are lots of ultra-modern buildings on the MIT campus and these make for great foils to Harvard’s more traditional styles.

    As you leave MIT, you will be greeted by the Charles River and the Boston skyline in the distance. This shoreline has one of the best views of the city and is a great place to catch the sunset.

    If you’d like a nice quiet place to reminisce about the day, head to nearby Kendall Square Roof Garden, which is one of the best secret places in Boston.

    mit great dome cambridge boston travel guide

    Day 3: South and East Boston

    On the final day of our travel guide for Boston, we’re going to explore the edges of the city. We’ll drop by the infamously unabashed South Boston, revisit the outskirts of Downtown, and then finish at the tragically underappreciated East Boston.

    Let’s start in South Boston – home of Irish haunts and all things “wicked.” South Boston had a bad wrap for a lot of years, being the headquarters for much of the city’s organized crime, but it has really cleaned up its act in recent years.

    South Boston aka Southie is now one of the most desirable areas of the city.

    The most noticeable trait of South Boston is the Southie accent, which has served as the inspiration for just about every bad Boston impression. While the accent isn’t as strong these days, hearing some old Southie ask for a “qua-ffee regula” from Dunkin Donuts might really make your day. Eavesdrop on some local banter before the accent disappears altogether.

    Next, head up to the South Boston Waterfront. This district is undergoing a huge renaissance and is home to many of the city’s best museums. Here you’ll find excellent institutions like the Children’s Museum, Institute of Contemporary Art, and Tea Party Museum.

    Wrapping up South Boston, head across the channel and back into the Downtown area. You’ll first run into Chinatown/Leather District but head north to eventually arrive at the Long Wharf.

    The Long Wharf is home to many of the city’s most well-known attractions, including the Boston Aquarium and Quincy Market.

    From the wharf, you can catch a water taxi to East Boston and then walk to Lo Presti Park. With unbeatable views of the city and plenty of athletic facilities, there are few better things to do at night in Boston than hang out here.

    harbor and boat boston travel guide

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    FAQ on Things to Do in Boston

    Here are some quick answers to common questions about what to do and see in Boston.


    Boston is pretty much an amazing city. There’s all that history of American Independence, the colonial period before that, and that’s before you even start looking into just how culturally rich this city is. From some of the best pizza in America, thanks to its Italian community, to some awesome Irish pubs (thanks to the Irish, of course), food and drink is a great way to get around in Boston. But there’s more to it than that.

    There’s kooky characters, spooky tales, and even college hijinx that have made their impact on the city – one of the most beautiful, historic and actually interesting in all of the United States.

    Bye for now, but not forever!

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