Weekend in Boston: The Perfect 2 Day Itinerary

Even with just 2 days in Boston, you can cover some serious ground and get a good feel for the city. Read on for a detailed itinerary for how to make the most out of a weekend stay in the Massachusetts capital.

Few cities in the United States hold more historical importance than Boston. To say that a lot of important history has unfolded here is a vast understatement.

When spending a weekend in Boston, you’ll get an insight into the city’s storied past through its countless landmarks.

In addition to getting a history lesson, you can take in the beautiful scenery of Boston in its parks and along its waterfront. Between the Charles River, Boston Harbor, and the Atlantic Ocean, around a quarter of Boston’s area is actually water.

With two days in Boston, your tastebuds are in for a treat when you indulge in the city’s famous seafood. Get excited for some mouthwatering clam chowder and lobster rolls (locally known as chowda and lobsta).

There are plenty of other options here as well, from rooting for the home team at historic Fenway Park to visiting the library of one of the country’s most beloved presidents.

Boston is home to world-class museums and you can also tour some of the best universities in the world. 

Here’s my itinerary for spending the perfect weekend in Boston.

Day 1 in Boston

For the first day, we’ll focus on checking off many of the city’s historical attractions.

Along the way, there will be several opportunities to enjoy some window shopping, grab a bite to eat, discover hidden gems, and relax with a beverage of your choice.


Speaking of beverages… I don’t know about you, but I’m pretty useless before I’ve had a cup of coffee. Start off at a local cafe before a big day of exploring. A few convenient options include Thinking Cup and Tatte Bakery & Cafe.

I chose these cafes due to their proximity to our first stop of the day — Boston Common. It’s been around since 1634, making it the oldest city park in the United States.

A nice stroll in the park is a great way to start off your weekend in Boston. Check out the beautiful Boston Public Garden or relax by the Frog Pond for a bit before hitting the Freedom Trail.

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weekend in Boston

This 2.5-mile Freedom Trail takes you to 16 different historical attractions across the city. It starts at Boston Common and passes by landmarks such as the King’s Chapel and Bunker Hill.

A great way to experience this important piece of American history is by taking a Freedom Trail walking tour. Those who prefer a DIY approach can click here for a PDF map to make your own walking tour.

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You can get an audio narration and a live GPS on your smartphone for just a few bucks if you just click here.

Many of the sights along the Freedom Trail are totally free to visit, but a few of them require an entrance ticket, such as the Old State House Museum and Paul Revere’s house.

It’s worth considering the Go Boston pass if you want to visit ticketed sights. They have a few different options and the savings are great if you plan to do a lot of sightseeing.

If you enjoy more of a personalized outing, check out the offerings on Airbnb experiences. There are several highly-rated tours with locals that will make a nice addition to your 2 days in Boston itinerary.


However you choose to visit the Freedom Trail, the perfect stopping point is Faneuil Hall.

Once upon a time, this was a meeting place for revolutionaries. That’s why it’s referred to as the “Cradle of Liberty” for its role in the independence movement.

These days, Faneuil Hall is a large marketplace full of different merchants along with several restaurants and bars.

There’s no time like the present to try some of the city’s famous seafood at places like Wicked Lobsta and Boston Chowda. Go ahead and work on your Boston accent while you’re at it.

For a full list of all the options at Faneuil Hall, head over to their website.

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There’s plenty of shopping to be done here as well if you’re looking to take home a souvenir. Don’t leave before taking in some of the amazing street performances that go on throughout the day out front. 

From here you have a few different options. Those moving along on the Freedom Trail can head to Paul Revere’s house, the USS Constitution and finally Bunker Hill. If you’re motivated, it’s definitely possible to tackle the whole trail in just one day.

For those who aren’t quite as passionate about history, you can head over to Boston Harbor instead. One really fun option down here is hopping on a duck tour. 

quincymarket Weekend in Boston: The Perfect 2 Day Itinerary
weekend in Boston

This has nothing to do with the birds that quack but rather with the amphibious vehicle of the same name. On these tours, you’ll cruise around by land and sea to take in the views of Boston.

Just click here to learn more about this highly-rated, super fun tour and book your tickets.


For those who finished up the Freedom Trail, you can just spend the rest of your evening over there in Bunker Hill/Charlestown. Options include the legendary Warren Tavern as well as the Brewer’s Fork beer garden. 

Speaking of beer, did you know that beer actually played a large role in the history of Boston and the country as a whole?

It was right here in Boston’s taverns that revolutionaries like Sam Adams and Paul Revere gathered to share ideas over a few frosty mugs of beer. 

Hop on this historic pub crawl to visit some of the city’s oldest taverns. Each one dates back to the 1800s and some are even older.

In addition to sharing stories, your guide will also recommend some beers that you can only get in Boston. Tours run at either 3 or 7 PM.

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Beer lovers may want to consider adding a tour of the legendary Samuel Adams brewery to their itinerary. It’s one of the most famous beers in the country and you can jump on a tour between 11-5 on Saturdays. Head to their website to see the options and book your spot.

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weekend in Boston

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Day 2 in Boston

With just 2 days in Boston, you’re going to have to make some choices.

Unfortunately, you can’t see it all in just one weekend! That’s why I’ll present you with a few options for how to spend day two. What you do will depend mostly on the time of year you visit and your interests.


Ease into another big day of exploring Boston with a leisurely brunch. Peregrine in the Whitney Hotel is an excellent choice, as is The Emory. Call ahead to make a reservation to avoid disappointment and long waits. 

After a big meal and perhaps a little bit of the bubbly, you have some choices to make. If you want to continue the history lesson we started yesterday, you can check out the Boston Tea Party Ships & Museum.

Here you have the chance to relive one of the most important events in the country’s history by dumping boxes of tea overboard in protest. Tickets cost around $30 and you can click here to book them online in advance. 

Another option for history buffs is the JFK Presidential Library. Learn all about the life of the 35th President of the United States and Boston native through interactive exhibits that include a vast collection of personal documents. Tickets cost $14 and can be booked on their website.

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weekend in Boston

The Boston area is home to some of the most prestigious universities in the world, including MIT, the University of Massachusetts, and Harvard. Two of which are named in the top 3 universities in the world — making them top attractions in Boston

You can explore the Harvard campus on a walking tour led by students. There’s the option to tack on a visit to the Museum of Natural History as well if you’re so inclined. 

It’s also possible to make your own tour of Harvard. Just click here to download a free map along with an accompanying audio tour.


In the afternoon, it’s time to head to the Back Bay area of the city which is home to trendy Newbury Street.

Full of historic brownstones, this scenic street has tons of boutique shops, cafes, restaurants, and bars to choose from. Click here for a rundown of all the various options.

One place you should definitely check out is Newbury Comics. Here you’ll find a vast collection of pop culture memorabilia, from comic books to vinyl records.

Even if there isn’t a game going on, it’s well worth it to make the short trip over to Fenway Park. Home to the storied Boston Red Sox baseball team, this is the oldest ballpark in the country.

Built over a century ago, Fenway is known as “America’s most beloved ballpark.” It’s definitely a special place to visit, and you can do so on an hour-long guided tour. These go on sale 30 days in advance and are available on a first-come, first-serve basis.

Of course, it’s preferable to visit Fenway Park for an actual ballgame. As one of the smallest parks with one of the most successful teams in recent memory, tickets are not easy to come by.

If you’re planning a weekend in Boston and the Sox are in town, it’s best to secure your tickets well in advance.

It’s well worth splurging on good seats to see a game in this legendary ballpark. Grab some peanuts and Cracker Jacks and root, root, root for the home team.

Should you strike out on getting tickets or if there isn’t a game, another option over here is the Back Bay Fens park. Enjoy a peaceful stroll through a World War II-era community garden and a rose garden. There’s also a WWII Memorial and a Japanese Bell here.

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weekend in Boston

I realize that not everyone is interested in seeing a baseball stadium whether there’s a game or not.

If you get beautiful summer weather on your 2 days in Boston, you may want to spend your afternoon at Castle Hill. It’s home to the historic Fort Independence, which is only open in the summer. There are free tours led by volunteers between noon and 3:30.

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You can also just kick back and relax at the scenic Pleasure Bay Beach. I bet you weren’t expecting a little beach getaway in the middle of your Boston weekend trip!

Another fun option for a weekend afternoon is this VIP brewery & beer tasting tour. It includes stopping at 4 different breweries to sample some tasty craft beers, as well as a hearty lunch or dinner.

You’ll get to sample some of the finest suds in the city and enjoy a beautiful buzz for the rest of your day.

If you didn’t take the Sam Adams tour on day one and still want to visit a big brewery, Harpoon is located right near the harbor and also runs tours until 5:30 on Sundays. You can also just visit the taproom for some food and a few cold ones.


It’s been a pretty wild two days in Boston so far.

You’ve covered a ton of ground in a short time and finished up a whirlwind tour of the city. That’s why it’s time to do whatever your heart desires on your last night in town.

As an avid live music fan, my personal recommendation would be to head to a show. Boston has a thriving music scene with venues of all shapes and sizes. I always check Jambase to see who’s playing in a city when I travel.

Perhaps you just want to chill out and have a drink. It’s right there in the name at Drink – a hip bar that’s “dedicated entirely to the craft of the cocktail.”

They’re so confident in their drink mixing abilities here that they don’t even have a menu. Drinks are created especially for your taste with the freshest ingredients. 

Your weekend in Boston can also come full circle if you head over to 21st Amendment. If you’re not well-versed in US history, the 21st amendment repealed the 18th one, officially ending the prohibition of alcohol.

They have a trivia night on Sundays, which is a fun way to end the Boston weekend.

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weekend in Boston

Weekend in Boston for Foodies (top 5 experiences)

I’m going to add a whole section here for a foodie’s weekend trip to Boston. There are some really fun, highly rated, and affordable food and drink experiences that you can enjoy in the afternoon, or evening.  

1. Politically Incorrect Food Tour – eat your way through Boston’s North End (Little Italy), with a true local — born and raised. Discover the authentic spots (no tourist traps) in the north end, and enjoy lots of food, stories, and laughs. Find out more here.

2. North End Little Italy Food Tour – another Italian tour run by a born and raised local! The difference between this tour and the one above is the spots you’ll stop at. If you’re into cheese, pizza, meats, and pastries, this one is for you. Learn more here.

3. Underground Donut Tour – not only will you sample interesting (and tasty) donuts, but you’ll be walking and learning about the history of Boston from the local guide. Learn more here.

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4. Lobster Roll and Mobster Stroll – feast on a tasty lobster roll, chips and a drink before joining a walking tour to learn about Boston’s crime history. Including the walking tour and lobster roll, it’s about a 3.5-hour experience. Find out more here

5. Dumpling Making Party – this is more of a cooking class and eating experience! Join restauranteurs and founders of the Joyce Chen Dumpling Festival and learn how to make tasty dumplings in a fun environment. Tapas, tea and snacks are included…and dumplings. Learn more here.

Insider’s Tips for a Weekend in Boston

I hope you have an awesome time in Boston with the help of this itinerary. I’m sure you’ll have an even better one if you follow these tips as well:

Skip the winter – This itinerary is best suited for the warmer months. It would not be nearly as enjoyable in the often bitter cold Boston winter. 

Book early for summer – Summer in Boston is great. There’s no doubt about that. Sox games, beach days, outdoor concerts, beer gardens, and more. You’re not the only one with the bright idea to spend a summer weekend in Boston, though, so book early.

Check the calendar – There are lots of big events going on in Boston throughout the year. It’s best to check the calendar to see what’s going on. If you end up there the weekend of a playoff game or a big music festival, it might be a little chaotic trying to pull off this itinerary.

Talk to the locals – This applies everywhere you travel, but I feel like I need to make it a point here. I only spent a weekend in Boston but had several great conversations with locals. They’re enthusiastic about sharing advice and recommendations for their city, plus you get to hear the awesome Boston accent. 

Go to a game – I know not everyone is interested in sports, but this city is incredibly passionate about its teams. This is especially true of the Red Sox. Do your best to make it to a game, or at least crowd into a local sports bar if you can’t snag tickets. 

Getting to Boston

Those traveling to Boston by plane will arrive at Logan International Airport (BOS). This is a major hub with direct flights to all corners of the globe.

It’s located in East Boston just a few miles from downtown. You have a few different options for how to get there. The most economical and environmentally friendly is taking the T. 

Logan Airport aerial view Weekend in Boston: The Perfect 2 Day Itinerary
weekend in Boston

Taking the T (MBTA)

The “T” is short for the MBTA (Massachusetts Bay Transportation Authority) and refers to the city’s efficient public transportation system. There’s a way to use the T no matter where you’re staying in Boston.

If you’re staying downtown, the Silver Line bus route will take you to South Station. Best of all, it’s totally free! Those staying in other areas can use a free transfer to the Red Line as well.

It’s also possible to take the Blue Line subway, but you have to get a shuttle just to get to the station and then buy a ticket for $2.75. My vote goes for the free bus ride.

For a detailed look at all the options, head to the MBTA website.

By Taxi

Taxis are readily available as well but there’s no flat-rate option and there are some unscrupulous drivers about. If you insist on taking one, just make sure they use the meter and you can follow the route on your phone. Expect to pay around $20-25 for downtown.


Rideshare apps like Uber and Lyft both work from Logan as well. Note that there’s a $3.25 airport fee added to any trips to or from the airport.

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By Train and Bus

Boston is also easily reached via train or bus. In general, it’s easy to move up and down the East Coast and this is especially true between the big cities.

Amtrak has several routes passing through Boston. You can easily travel to or from Boston by train from NYC, Philadelphia, and Washington DC.

There are also several companies running bus routes, including Greyhound, BoltBus, and Megabus. I only have experience with the latter in Boston but it was fine and cheap. Book early and you can save a lot on your tickets.

Where to Stay With 2 Days in Boston

In the interest of convenience and comfort, it’s best to stay downtown on a Boston weekend trip. Doing so ensures you spend less time in transit between the airport, which is key for such a short trip to the city.

By staying downtown, you can easily use the free airport bus and probably just walk to your accommodation. I don’t know about you, but I want to spend more time exploring and less time in traffic. Boston in 2 days is doable, just make sure you choose accommodation in a good location. 

Staying downtown also puts you right in the middle of all the action. You’re right there near the Freedom Trail and the Waterfront, which is where you’ll be spending most of your time.

From here, it’s also easy to access places like Harvard and Fenway Park via public transportation. There are plenty of great options for places to shop, eat, drink, and stay here as well. 

Here are a few different options for where to stay in downtown Boston:

Budget: HI Boston (Hostelling International)
Mid-Range: Omni Parker House
Luxury: Four Seasons Boston

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weekend in Boston

If you want those harbor views and don’t mind paying a premium for them, you can search for hotels on the Waterfront as well. Back Bay is also a fun area to stay in for its proximity to Newbury Street and Fenway. 

I always do an Airbnb search of cities as well and there are some pretty solid options in Boston, especially if you don’t mind a room in a shared space. Click here to search for the best Airbnb options in Boston.

Enjoy Your Weekend Trip To Boston

While 2 days in Boston isn’t really enough time to get under the skin of the city, it’s certainly a nice introduction.

I’m sure you’ll have the same thought that I did, and that is “I’ll just have to come back and do it again!” There’s plenty to see and do here to warrant several return trips to this iconic American city.

I personally had an absolute blast with my weekend in Boston, soaking up the history on the Freedom Trail, digging into a big ole’ bowl of clam chowda, and cheering for the Sox (which was tough as a Tigers fan, believe me), and more.

Should you come back from your trip to the city with any excellent recommendations of your own, please drop a comment below and let us know. I hope you enjoyed this 2 days Boston itinerary.

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