Weekend in Boston: The ideal 2 Day schedule


even with just 2 days in Boston, you can cover some major ground and get a good feel for the city. read on for a comprehensive schedule for how to make the most out of a weekend stay in the Massachusetts capital.

Few cities in the united states hold much more historical significance than Boston. To say that a lot of essential history has unfolded here is a large understatement!

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

In addition to getting a history lesson, you can take in the stunning 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 well-known seafood. get thrilled 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 going to the library of one of the country’s many beloved presidents. Boston is home to world-class museums and you can also trip some of the best universities in the world. 

Here’s my schedule for spending the ideal weekend in Boston! 

Day 1 in Boston
Day 2 in Boston
Insider’s suggestions for a weekend in Boston
Getting to Boston
Where to stay With 2 Days in Boston
Enjoy Your weekend trip To Boston

Day 1 in Boston

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

Along the way, there will be several opportunities to delight in some window shopping, get a bite to eat, discover hidden gems, and unwind 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 because 1634, making it the oldest city park in the United States.

A good stroll in the park is a terrific way to start off your weekend in Boston. check out the stunning Boston Public garden or unwind by the Frog Pond for a bit before hitting the freedom Trail.

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 terrific way to experience this essential piece of American history is by taking a freedom trail walking tour. Those who choose a diy method can click here for a PDF map to make your own walking tour.

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 completely totally free to visit. 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 check out ticketed sights. They have a few different options and the savings are terrific if you plan to do a lot of sightseeing.

If you delight in much more of a customized outing, check out the offerings on Airbnb experiences. There are several highly-rated trips with locals that will make a good addition to your 2 days in Boston itinerary. 


However you choose to check out the freedom Trail, the ideal 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 well-known 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.

There’s plenty of shopping to be done here as well if you’re wanting to take home a souvenir. Don’t leave before taking in some of the fantastic 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 certainly possible to tackle the whole trailin 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. 

This has nothing to finish with the birds that quack but rather with the amphibious car 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 much more about this highly rated trip and book your tickets.

Another option is this informative sightseeing cruise. You’ll spend an hour and a half going around the inner and outer harbor while learning much more about the city’s history. 


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 best 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 check out 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. trips run at either 3 or 7 PM. 

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

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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 check out and your interests.


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

After a big meal and possibly 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 essential events in the country’s history by disposing boxes of tea overboard in protest. Tickets cost $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 large collection of personal documents. Tickets cost $14 and can be booked on their website.

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 trip led by students. There’s the option to tack on a check out to the museum of natural history as well if you’re so inclined. 

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


A terrific option for kicking off an afternoon in Boston is a trip up to the Skywalk Observatory. From the 50th floor you’ll get some epic views of the city. Tickets are $21 if you purchase separately and it’s also included in the Go Boston Card.

It’s located in the Back Bay area of the city, which is home to trendy Newbury Street.

Full of historic brownstones, this beautiful 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 ought to certainly check out is Newbury Comics. here you’ll find a large 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 theshort 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 many beloved ballpark.” It’s certainly a special place to visit, and you can do so on an hour-long guided tour. These go on sale 30 days in advancement and are available on a first-come, first-serve basis.

Of course, it’s more suitable to check out 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 protected your tickets well in advance.

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

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

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

If you get stunning 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 totally free trips led by volunteers between midday and 3:30.

You can also just kick back and unwind at the beautiful pleasure Bay Beach. I bet you weren’t expecting a little beach trip 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 delight in a stunning buzz for the rest of your day.

If you didn’t take the Sam Adams trip on day one and still want to check out a big brewery, Harpoon is located best near the harbor and also runs trips until 5:30 on Sundays. You can also just check out 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 trip of the city. That’s why it’s time to do whatever your heart desires on your last night in town.

Of course, I’m not going to leave you hanging with no recommendations! A terrific way to spend your final evening in Boston is by taking a sunset cruise around the harbor. 

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 best 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.

Insider’s suggestions for a weekend in Boston

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

Skip the winter season – Th

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