Boston, Massachusetts is a coastal city that truly has it all, from fascinating history and lush green spaces to incredible food, shopping, and sports. Every neighborhood has its own personality and charm, making it one of our favorite cities to explore. Whether you’re diving into American history, catching a game, or indulging in fresh seafood, Boston is a city you will definitely want on your travel bucket list.
But what makes Boston really special is the way old and new blend together into a pretty walkable city. You’ve got centuries-old buildings and streets right next to cutting-edge tech and some of the best universities in the world. And interspersed by plenty of water and green space to balance the urban setting.
It’s also maybe the best sports city of the last two decades, but I (Jake) grew up around here, so I might be a little biased.
So let’s dive into the best things to do in Boston, MA.
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Map Of The Boston Area
Use this helpful map of the Boston area to find all the best attractions in one place. And to help plan your perfect trip.
Go City Pass
Real quick, before we get into this epic list, we wanted to mention the Go City Pass.
It’s a flat-rate exploration pass that gets you discounted access to some of the best attractions in the area. Many of which we list below.
You can either choose the 1-day all-you-can-explore pass, or a multi-attraction pass to complete at your leisure over 30 days.
And the GoCity Pass also includes access to some attractions in nearby Salem, Massachusetts. Check our travel guide for Salem to learn more about the infamous home of the Witch Trials and the epicenter of Halloween and all things spooky.
The Freedom Trail
The Freedom Trail is Boston’s most historic site that stretches 2.5 miles through the city. Together, these sites are the most complete and well-preserved landmarks of the American Revolution.
For the most complete experience, I recommend joining a guided tour, with knowledgeable guides who can really bring the stories of the past to life.
Or you can do it self-guided, spending as much or as little time as you like at each site. And thankfully, you can follow a red brick path through the city to all of these sites. Because Boston’s street layout is notoriously lacking a unifying pattern.
Using something like Alltrails can help you stay on track and provide a little extra background about each site.
Or another option is to purchase an audio tour, which gives a little more flexibility to see the sites on your own schedule.
There really is no right or wrong place to begin the trail, but if you want to complete it from end to end, it’s best to begin at the Boston Commons in Downtown, or at Bunker Hill in Charlestown. You can experience a good amount of it in just a couple of hours. But to really do everything, it’s probably best to break it into 2 or 3 days, while mixing in some other attractions along the way.
Most sites include at least some informational placards about their significance. While others allow entry or have dedicated museums. (Admission fees may apply)
Some of our favorite sites on the trail are the USS Constitution, the Old North Church, the Paul Revere House, the King’s Chapel Burying Ground, and Boston Common.
But here’s a complete list of all the sites on the Freedom Trail:
- Boston Common
- Massachusetts State House
- Park Street Church
- Granary Burying Ground
- King’s Chapel and King’s Chapel Burying Ground
- Boston Latin School Site/Statue of Benjamin Franklin
- Old Corner Bookstore
- Old South Meeting House
- Old State House
- Boston Massacre Site
- Faneuil Hall
- Paul Revere House
- Old North Church
- Copp’s Hill Burying Ground
- USS Constitution
- Bunker Hill Monument
And another one that’s not on the Freedom Trail, that you might be interested in, is the Boston Tea Party Museum.
Book A Small Group Freedom Trail Guided Tour
Go On A Boat Tour
The city of Boston is surrounded by water, with several rivers winding inland and the Atlantic Ocean to the east. So going on a boat tour is a great way to experience the sights of Boston.
Some of the most popular tours are the Duck Boat Tours, Harbor Sunset Cruise, and Whale Watching.
The Duck Boats are amphibious vehicles that are iconic to Boston. The tours offer a perfect blend of land and sea. And they also make good parade floats anytime we win a Championship.
Boston Harbor City Cruises operates a variety of different tours. We went on the Harbor Sunset Cruise. And enjoyed a colorful and glowing sunset over the city. And the tour guide kept us entertained with stories and interesting facts about the area.
Did you know that about 3/4s of all the land Boston sits on is man-made? Present-day Boston is almost unrecognizable from the original peninsula surrounded by tidal flats.
Book A Sunset Cruise With Boston Harbor City Cruises
The North End Neighborhood
This is definitely our favorite neighborhood in all of Boston. Nowhere else proves my point better about different neighborhoods having their own distinct feel. This area is sometimes referred to as “Little Italy”, because the North End is famous for rich Italian-American heritage, short brick buildings, and some of the most famous historic sites on the Freedom Trail, like the Old North Church, Paul Revere’s House, and Copp Hill Burial Ground.
Unlike other parts of the city with skyscrapers, the steeple of the Old North Church still stands high above the other buildings. Preserving the legacy of the steeple used to warn of British Troops, “One if by land, Two if by sea”.
It’s fun to wander the narrow streets of the North End, which has a sort of European vibe. You practically can’t throw a rock here without hitting an excellent Italian restaurant. If you are looking for the really upscale ones, Carmelina’s and Giacomo’s are consistently ranked highly.
But one we love that’s a little more affordable is La Famiglia Giorgio. Excellent flavors and generous portions.
The other cuisine that the north end is famous for are the pastry shops. Mike’s Pastry, Modern Bakery, and Bova’s serve a mouthwatering variety of pastries and other specialties, like cannolis, Boston cream donuts, calzones, arancini, and more.
Mike’s Pastry is the most famous one. But be warned, it’s cash only and the lines here can get crazy. But dang, were these cannolis massive and delicious. And the cheesecake was incredible too.
Oh and don’t even think of driving a car into the North End. Between the confusing and narrow one-way streets and the lack of parking, I promise you, you’re better off going in on foot. Or at least getting dropped off.
Join a North End Food Tour
The View Boston
Emily and I are suckers for a good view, and The View Boston certainly delivers on that name. At the top of the Prudential Tower, Boston’s second-tallest building, The View provides an unparalleled sightseeing experience. But of course, we recommend visiting on a clear day, or sunset is also a nice time to visit.
A speedy elevator whisks you up to the 52nd floor, opening up to 360 views of Boston. From the Charles River, to Fenway Park, to the Boston Harbor and beyond. It’s fun to try to pick out landmarks that you know, or learn about some new ones.
And atop the building you can enjoy some drinks and apps from the Stratus Bar. Or a sit-down meal at the Beacon Bistro.
And they also have several interactive media exhibits to learn about Boston’s most iconic neighborhoods and attractions. Even helping you to craft your own itinerary.
Tickets to The View range from entry-only tickets for $34 for adults to various food and drink packages between $45 to $125.
Book Tickets For The View Boston
Go To A Red Sox Game
Built in 1912, Fenway Park is the oldest MLB stadium, and one of the nation’s most beloved ballparks. Crammed right into the city, left field is famously cut short by the Green Monster, a giant wall pinned right along Lansdowne street.
The energy in the city before games is just so fun. We love to pop into some nearby bars to pregame with other fans.
Bukowski Tavern is a local, little hole-in-the-wall bar that’s our favorite place to start.
And then when you’re ready to get into the madness, the Bleacher Bar is literally right under the stadium, with a window looking out onto the field. It’s usually pretty crammed in here, but worth checking out at least once.
And as long as they’re not playing the Yankees, tickets to see the Red Sox are surprisingly affordable. We scooped some up in right field for less than $20 each.
Or they also offer various tours of the Stadium if you can’t fit in a game.
Book A Fenway Park Tour
Get Some Seafood
When you’re in New England, you gotta try some local seafood. Many iconic seafood dishes, literally known around the world can be found right here. From plump lobster rolls and creamy New England clam chowder, to succulent mussels, and the always polarizing raw oysters.
Fresh Seafood comes in daily right off the boats in the Seaport District, Boston’s newest hip neighborhood. But you can find seafood restaurants all over the city.
One of our favorite casual seafood spots is The Barking Crab. It sits in this colorful dockside tent with nice views of the city. You can get all the classic pub-style seafood classics here.
If you’re looking for something more upscale, Row 34 is an industrial and hip seafood spot, famous for their extensive raw oyster bar.
Some other popular ones, are Row 34, Union Oyster House, and Legal Seafoods.
Book A Boston Seafood Tour: Behind The Scenes
Fan Pier Park
Fan Pier Park offers one of the best views of the Boston skyline. If you grab a fresh lobster roll from The Barking Crab, this scenic spot is just around the corner. You might pass by it on a harbor or boat tour, but there’s something about the chain-link fence and waterfront backdrop that makes it one of those quintessential Boston photo spots.
Charles River Esplanade
Our favorite green space in Boston is the Charles River Esplanade. The River snakes its way inland, flanked by the Back Bay neighborhood on one side and Cambridge on the other. And all along the river, there are parks with walking and biking paths, playgrounds, and more.
It’s a nice place to stroll along the river and take in the sights. On the north bank, you get great views of the Boston skyline over the river, and pass by two prestigious universities, MIT and Harvard.
And it’s scenic to watch all the boats from the collegiate crew and sailing teams.
We rented bikes with Urban Adventours because it was one of the options included in the Go City Pass.
Or Blubikes is a popular bike-share program that offers e-bikes for rent all around the city.
The Museum Of Science
This is Boston’s most exciting and interactive museum. While somewhat geared more towards kids, there’s plenty of stuff that appeals to adults too.
With exhibits from all disciplines of science, from biology and chemistry to astronomy and engineering, you’ll find many things that stoke your sense of curiosity and wonder.
The museum also has 3 exciting movie theaters. From a 5-story domed IMAX theater to the multi-sensory 4D theater. All movie showings require an additional fee and a reservation.
The New England Aquarium
The New England Aquarium is an awesome stop for marine lovers. With exhibits from all around the world. From piranhas of the Amazon Rainforest to playful penguins and vibrant Indo-Pacific coral reefs, there’s plenty to explore here.
One of the most notable features is the Giant Ocean Tank, that a four-story cylindrical coral reef tank. It holds nearly 200,000 gallons of water and houses sea turtles, sharks, rays, eels, barracudas, plus many reef fish. Visitors can circle the tank along a spiraling walkway, catching new perspectives from different viewing decks.
Don’t miss the Shark and Ray Touch Tank, where you can gently interact with these graceful creatures up close.
One super unique attraction is seeing Myrtle, a green sea turtle, who has been at the Aquarium since 1970.
Quincy Market
Quincy Market is one of Boston’s original market buildings, turned buzzy modern food hall. It’s located right next to Fanueil Hall, one of the stops on the Freedom Trail.
Just stroll through the market and discover something tasty to eat. From local classics to cuisines from all over the world.
You can dine inside, or take the food outside to the pedestrian-friendly outdoor mall.
There is always some action around here, with street performers to entertain you while you chow down.
But just be warned, Quincy Market can get wildly crowded on weekends. Like so, shoulder to shoulder, you can barely walk. So try to come at off-peak times if you can.
Visit Some Breweries or Pubs
Boston is famous for having an excellent collection of pubs and breweries. And, specifically, there are lots of Irish Pubs, with nearly a quarter of Boston residents claiming some Irish heritage.
Some of our favorite Irish Pubs are The Black Rose, The Green Dragon, and Durty Nelly’s. But there are many many more.
And there’s a variety of nice breweries to check out as well.
Of course the most famous Boston brewery is Sam Adams. Their brewery is a bit outside Boston proper in a neighborhood in Jamaica Plain, and is a popular for tours. But their downtown taproom near Quincy Market makes for a more convenient place to try their beers right downtown. And they brew much more than just the flagship Boston Lager, so everyone will find something to enjoy.
Probably the next biggest brewery in Boston, and my favorite, is Harpoon, located in the Seaport District. Harpoon offers an awesome $5 tour that includes free tastings. And also have a beer garden and outdoor patio to enjoy some beers and light food.
There are quite a few other good breweries with tasting rooms in and around the city. A couple that we really like are Trillium, Lord Hobo, Cisco, and Tree House.
JFK Library & Museum
For history buffs, you should definitely check out the JFK Library and Museum. The Library’s mission is to preserve and provide access to historical materials about JFK and his era. You can find displays of artifacts, documents, photos, recordings, and memorabilia from JFK’s life, presidency, and legacy.
It costs $20 for adults, $16 for seniors, $10 for college students, and free for youth (17 years and under) and UMass students.
Tour the Boston State House
One free thing to do in the city is tour the Boston State House. It houses the state legislature and the offices of the Governor. Tours are offered weekdays, from 9:00 am – 5:00 pm by docents. You can learn about the architecture, construction and view beautiful murals within the building.
Swan Boats in Boston Common
Something that’s kinda iconic in Boston are the Swan Boats in Boston Common. Boat tours were offered as early as 1877 and it’s still operated by the same family that started the tours. You can grab tickets right at the dock, and each boat can fit up to 12 passengers. It costs $4.75 per person and runs about mid-April until early September.
Explore Castle Island
Castle Island is a 22-acre park in South Boston. It was originally its own island, but since 1928, land reclamation and causeways have connected it to the mainland. Since the 1600s, this site has been continuously fortified. It played important roles during the Revolutionary War, both World Wars, and more. Today, you can visit Fort Independence here, the 8th fort constructed on this site.
Explore Beacon Hill
Beacon Hill is one of Boston’s oldest and most historic neighborhoods. You can find it just north of the Boston Common. The name “Beacon Hill” comes from a signal beacon that once stood on the hill, used to warn of invasion or danger. Acorn Street is the most picturesque spot, with its original cobblestone road squeezed between old brick buildings.
Museum Of Fine Arts
The Museum of Fine Arts in Boston is one of the most impressive art museums in the country, home to nearly half a million works that span everything from ancient Egyptian artifacts to modern masterpieces. While many exhibits are part of the museum’s permanent collection, there are also rotating special exhibitions that bring in new artists and themes throughout the year.
General admission is $30 for adults, $14 for youth (ages 7–17), and free for children under 6. If you’re visiting on a budget, don’t miss the museum’s $5 admission nights on the third Thursday of each month.
Tour or Show At Wang Theater
The Wang Theater is a beautiful and historic performing arts theater. It has one of the largest stages in the country. You can watch many different shows from broadway, dance, comedy, concerts, holiday spectacles, etc. Check out their events page to see if a show is taking place along your visit.
Explore Chinatown
Chinatown is one of Boston’s oldest neighborhoods. It’s a vibrant cultural, commercial, and residential hub, especially for Asian immigrant communities. Food is the major draw here, as they offer just about every Asian cuisine. And they celebrate many popular Asian festivals as well. Just exploring the area is unique and a fun way to experience a different culture in the city of Boston.
The Q (restaurant)
While there are so many tasty and authentic restaurants to try in Chinatown, you gotta check out The Q restaurant for some amazing Asian-American fusion cuisine. Their Mongolian Hot Pot is a must-try. It’s a classic northern Chinese dish that is served in flavorful broth, where you can add any ingredients you want to it. It’s known for having fast and friendly service.
Bell In Hand Tavern
The Bell in Hand Tavern is America’s oldest tavern that has been in continuous operation. It was established in 1795 by Jimmy Wilson, who was the town crier (“a person employed to make public announcements in the streets or marketplace of a town”). But the building it lies in now, was not it’s original location, it’s actually changed establishments a few different times.
Galleria Umberto (Pizza North End)
If you’re looking for best, no-frills pizzeria in Boston, then for sure stop into Galleria Umberto. It’s known for it’s Sicilian-style pizza slices. It’s cash-only and can sell out on busier days. It actually received a James Beard award in 2018, for being one of “America’s Classics”.
Where To Stay In Boston
Of course Boston being in a city, there are tons of great places to stay. Here are some of our personal recommendations. Or use the map below to search various places for your perfect location.
- Boston Harbor Hotel – 5 Star, waterfront hotel, very upscale, walkable to waterfront attractions
- The Revolution Hotel – Good budget option, basic rooms (some with shared bathroom), good location to many major attractions
- The Dagny Boston – Stylish hotel near the waterfront, great location, mid-tier price
- Boston Marriott Long Wharf – Excellent location, higher-end price point, walkable to tons of great activities, on waterfront
- The Godfrey Hotel Boston – Stylish hotel, close to best attractions, good value room
- Found Hotel Boston Common – Hostel style, best budget and most affordable option, very walkable or quick uber to great attractions
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