How to Spend Four Days in Boston

As one of the most historic cities in the United States, Boston has a lot of interesting things to do. It’s not as large as New York or Chicago, and it often feels more like a giant town than a city. I think that’s a plus, because Boston offers all the benefits of a big metropolis without the intensity and fast pace of New York.

Boston isn’t a city to rush through. Unlike many other destinations, people who visit Boston tend not to do it in a day or two. It’s as if they already know this is a relaxed city that deserves a bit more time. I think you can get a very good feel and overview of Boston during a four-day visit. Here’s an itinerary that will allow you to see the best of what Boston has to offer:

Day 1
Freedom Trail
Boston's Freedom Trail sign is fits in nicely
The Freedom trail is a 2.5-mile walk through historic Boston. It takes you through all the major sites and monuments. To see all the sites on the trail, expect it to take up most of your day. Given all the walking that’s involved, I would make this the only activity of the day. You’ll want to take your time and see all the sites. After all, Boston has a very long history. It may be “super touristy,” but it does an amazing job of presenting the history of one of America’s oldest cities.

Lunch in Faneuil Hall
– Quincy market in Faneuil Hall is the best place to stop and eat lunch on the Freedom Trail. There are about two dozen different places to eat. You can get just about anything here from Greek to sushi to sandwiches and much more Since you’re in Boston, try the clam chowder, a local New England specialty.

Day 2
Boston Commons
Boston Commons is a great place to spend the day in the summer
Start your day in Boston Commons, a giant park that sees plenty of people on warm summer days. There are lots of different paths to take, including to the Frog Pond, where kids and adults can cool off. During the winter, there’s skating on the pond. Boston Commons is also a great place to go people watching.

Boston Public Gardens
A great place to spend a nice spring day is at Boston's Public Gardens
After your early-morning walk, head across the street to the public gardens. You can take a swan tour through the pond in the middle of the gardens or you can simply stroll around and see some pretty flowers.

Walk around the Back Bay – The end of the park meets Boston’s back bay, our version of New York’s SoHo and West Village. This is where Boston’s elite and wealthy live and nearby Newbury Street is our Madison Avenue, with lots of expensive shopping. The pretty brownstones and tree-lined streets make for a peaceful, leisurely stroll. Stop at the park on Commonwealth Ave to sit and watch the people and cars go by.

Lunch on Boylston – Move towards Boylston Street and eat lunch out on the patio of one of its many restaurants. If you want to spend a bit more money, eat on Newbury Street. Stephanie’s is good for both food and emptying your wallet. Snappy Sushi has great lunch specials, and Kashmir has delicious (and spicy) Indian food.

Copley Square and Trinity Church – Copley Square is a great little park where you can buy discount theater tickets, listen to musicians, and gaze up at the Hancock Tower. You can also go into Boston’s Trinity Church, which is one of Boston’s oldest and most beautiful churches.

Charles River
You can spend the day sailing and swimming in Boston's Sharles River
Double back towards the Charles River and walk the riverfront. If it’s summer time, you might be able to catch a free show at the Boston Hatch Shell or go sailing on the river. If not, it’s still a nice walk along the river where you’ll encounter runners, kids playing, and people playing sports.

Museum of Science
– At the end of the riverfront is the Museum of Science. If you aren’t too tired, check out the museum and the Omni Theater inside. Though many of the exhibits are for kids, it’s still one of the best museums in the country. Their outer space exhibit is outstanding.

Day 3
Visit the Aquarium – Boston’s aquarium is one of the better ones I’ve been to. It’s really well done, the fish aren’t all cluttered into a few small tanks, and there’s a lot of information about how to protect the oceans.

Explore the North End
The historic Italian north end of Boston, Massachusetts
The historic North End is the heart of Boston’s Italian community. You’ll hear just as much Italian as you will the Boston accent. In the morning, you’ll see little Italian grandmas shopping while the grandpas have their morning espresso. It’s almost like being in Italy. You’ll find the best gelato outside of Italy here.

Head Up to the Prudential Tower – Once you’re out of the North End, head back towards Copley to see the Prudential Tower. You can go up the tower and get a bird’s-eye view of the city.

Arnold Arboretum
Beautiful leaves falling at the Arnold Arboretum in Boston
Over 260 acres of free public space are open from sunrise to sunset. There are running trails, gardens, open lawns, and tons of flowers from all over the world. Relax among the plants and take a step back from the fast pace of the city. This place is much quieter than the Public Gardens and offers a wider variety of plant life. They also have a great bonsai tree collection.

See a Game – Boston is a sports town. Throughout the year, you’ll find sports teams playing. Bostonians are die-hard about their teams, so you’re sure to witness some intense feelings when you go. If you really want a Boston sports experience, go to a Red Sox’s game. If you can’t get in, hang out around the bars near Fenway. Just never, ever, ever root for the Yankees!

Day 4
Take a Free Tour of Harvard
The Harvard University campus in Cambridge is a great place to spend the day
Founded in 1636, Harvard is the oldest university in America. Head to its home in Cambridge (Harvard Square train stop, red line) and join a free tour. Learn about the university’s history, architecture, programs, and myths. When you’re finished, wander around and experience Harvard Square’s eclectic offerings. There are a lot of good street musicians to listen to. (Tracy Chapman got her start here.)

Hang out in Harvard Square
Harvard Square is the place to be at night in Boston
See the mix of life in Harvard Square. Walk around, stroll into used bookstores and coffee shops and watch artists, vagabonds, locals, and college students mingle. There are some cool little shops in “The Garage.”

Take the Sam Adams Brewery Tour – After four days of sightseeing, you deserve a beer or five. Sam Adams Brewery offers free tours of its brewery. Sam Adams is a major brewer in Boston and locals drink it widely and frequently. Tours start mid-afternoon and depart every 45 minutes. You get a few free samples along the way. If you’re under 21, don’t worry. You can still go, you just can’t drink.

Boston’s a great city, and I’m not just saying that because I grew up there. I’ve never encountered a person who hasn’t liked it. Come to Boston and find out what a great city it is. This four-day itinerary will give you a good overview of the city at a nice, relaxing pace. You’ll be moving around a lot, though, so make sure you get an unlimited “T” pass (train pass). If you have more time, you can squeeze in some other activities. But why rush such a beautiful place?

For more information on the United States, visit my country and city guides to US travel.

  1. I was able to visit the Harvard campus once during a trip to Boston. I was actually surprised that there are a lot of interesting sights to see there.

  2. Wendy

    I went to grad school in Boston and this is a great run down of the best to see and do. An insider tip: It’s actually called the Boston Common. Nothing will single you out as a tourist faster than calling it the Commons… or wearing a Yankees hat.



  4. This is a great list! I especially love to window shop on Newbury Street after a stroll through the Public Gardens. A Freedom Trail pub crawl is on my to-do list this summer/fall.

  5. As someone whose been living in the Boston area for a long time, I think that if it felt less familiar to me it would be a fascinating city to walk through. It seems to have an interesting blend of old and new in its architecture and neighborhoods. You can be in a small, quaint, hilly neighborhood like Beacon Hill, then turn a corner and be on a busy street with lots of shops and cars. It seems like every time you cross a main road into a different neighborhood its a different world.

  6. Maja

    I would recommend you budget at least 1/2 a day for the Museum of Science. It’s amazing at any age (I never get tired of the musical steps!!!) and between the exhibits, the Omni Theater, and the Planetarium, you have tons to see!

    I would also recommend a walk down Mass Ave (Massachusetts Avenue) starting around the Mass Ave T stop (Orange Line) to Harvard Square. It’s about 3 miles but it takes you from Boston to Cambridge, past MIT and through Central Square (an experience on its own), including crossing the river. It may not be a typical tourist path but it will give you some sense of Boston/Cambridge. You can also just take the 1 bus (which takes the same route) if you don’t feel like walking!

  7. Carmen

    This is awesome! Thanks Matt! Will do and see as much as we can. We’re here for a short 4 day stop from our trip to Iceland.

  8. Carlos

    Really great info! The pictures and the suggested tours make the travel plans even more interesting. Very well framed in different ways to ensure that we´ll have good quality time!
    I make my comments when I come back!

  9. Hey Matt, I really enjoyed your forum at the HI-USA National Gathering today. I’m really interested to see that you’re from Boston, but notice it’s been a while since you posted about Boston (which is understandable, since you started off here), but I wanted to be sure to make sure you knew about new HI-Boston Hostel, which opened in 2012. This award-winning Hostel has been built to LEED Gold standards, and hosts more than 50,000 guests/year. I hope you get the chance to stop by and check us out —

  10. I am wondering where I should stay to enjoy your itinerary at the top? I have two kids and I’m thinking this may be a wonderful trip to take over March break? Thank you for writing such a great post!!!

    So helpful!!!

  11. Also if you have extra time, I would recommend visiting the various ethnic neighborhoods for some great food, and the various venues for live music, especially in Cambridge

  12. As someone who visits Boston regularly (my sister lives there) this list is spot on. I’d also recommend the Boston Museum of Fine Art if you’re into that kind of thing.

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