Weekend in Boston: The Perfect 2 Day Itinerary for 2023

Even with just 2 days in Boston, you can imbricate some serious ground and get a good finger 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 places in the United States hold increasingly historical importance than Boston. When spending a weekend in Boston, you’ll get an insight into the city’s storied past through its myriad landmarks.

During my first action-packed visit, besides getting a history lesson, I made sure to enjoy the trappy scenery of Boston in its parks and withal its waterfront. Add in a unique and succulent cuisine, and I once have a long list of things to do for my next trip to Boston.

The Perfect Weekend in Boston

Read on for how to spend a fun-filled 2 days in Boston. Besides history and food, there are plenty of other options as well, from rooting for the home team at historic Fenway Park to visiting the library of one of the country’s most minion presidents.

Boston is moreover home to world-class museums and you can moreover tour some of the weightier universities in the world. And of course, 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).

Day 1 in Boston

One Day in Boston: Itinerary & Where to Go in 24 Hours

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

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


Speaking of beverages… I don’t know well-nigh you, but I’m pretty useless surpassing I’ve had a cup of coffee. Fortunately I had no trouble finding lots of unconfined local cafes in Boston. Two user-friendly options are 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 virtually since 1634, making it the oldest municipality park in the United States.

A nice stroll in the park is a unconfined way to start off your weekend in Boston. Trammels out the trappy Boston Public Garden or relax by the Frog Pond for a bit surpassing hitting the Freedom Trail.

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

A unconfined way to wits this important piece of American history is by taking a Freedom Trail walking tour. Those who prefer a DIY tideway 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 withal the Freedom Trail are totally self-ruling to visit, but a few of them require an archway 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 variegated options and the savings are unconfined if you plan to do a lot of sightseeing.


However you segregate to visit the Freedom Trail, the perfect stopping point is Faneuil Hall. I consider it a must-do in Boston and it was one of my favorite places to spend a slow afternoon.

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 variegated merchants withal 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 superiority and work on your Boston vocalizing while you’re at it.

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

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

From here you have a few variegated options. Those moving withal on the Freedom Trail can throne 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 well-nigh history, you can throne over to Boston Harbor instead. One really fun option lanugo here is hopping on a duck tour. 

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 trip virtually by land and sea to take in the views of Boston.

Just click here to learn increasingly well-nigh this highly-rated, super fun tour and typesetting 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. 

I hit them both in the same day, and they offered a nice taste of the historic side of Boston’s nightlife. Plus the beer was first-rate.

Speaking of beer, did you know that beer unquestionably 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 when to the 1800s and some are plane older.

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

Beer lovers may want to consider subtracting 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. Throne to their website to see the options and typesetting your spot.

Day 2 in Boston

How to best spend 24 hours in Boston - Places to See - Expat Explore

With just 2 days in Boston, you’re going to have to make some choices. During my first visit to Boston, it was on the second morning that I really had to consider how to weightier spend my time.

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 flipside big day of exploring Boston with a leisurely brunch. Peregrine in the Whitney Hotel is an spanking-new choice, as is The Emory. Call superiority to make a reservation to stave thwarting 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 protract the history lesson we started yesterday, you can trammels out the Boston Tea Party Ships & Museum.

I’ll never forget how much fun it was to relive one of the most important events in the country’s history by dumping boxes of tea overboard in protest. Tickets forfeit virtually $30 and you can click here to typesetting them online in advance. 

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

The Boston zone is home to some of the most prestigious universities in the world, including MIT, the University of Massachusetts, and Harvard. Two 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 moreover possible to make your own tour of Harvard. Just click here to download a self-ruling map withal with an twin audio tour.


In the afternoon, it’s time to throne to the When Bay zone of the city, which is home to trendy Newbury Street.

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

I expressly enjoyed some wide-stretching browsing in Newbury Comics. Here you’ll find a vast hodgepodge 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 minion 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 whop and are misogynist on a first-come, first-serve basis.

Of course, it’s preferable to visit Fenway Park for an very ballgame. Because it’s one of the smallest parks with one of the most successful teams in recent memory, tickets aren’t easy to come by.

If you’re planning a weekend in Boston and the Sox are in town, it’s weightier 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, flipside option over here is the Back Bay Fens park. Enjoy a peaceful stroll through a World War II-era polity garden and a rose garden. There’s moreover 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 trappy summer weather on your 2 days in Boston, you may want to spend your afternoon at Castle Island. It’s home to the historic Fort Independence, which is only unshut in the summer. There are self-ruling tours led by volunteers between noon and 3:30.

You can moreover just kick when and relax at the scenic Pleasure Bay Beach. I bet you weren’t expecting a little waterfront getaway in the middle of your Boston weekend trip! I fell in love with the place during the afternoon I spent relaxing in the sand.

Another fun option for a weekend afternoon is this VIP brewery & beer tasting tour. It includes stopping at 4 variegated 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 municipality and enjoy a trappy whoosh 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 moreover runs tours until 5:30 on Sundays. You can moreover just visit the taproom for some supplies and a few unprepossessed 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 voracious live music fan, my personal recommendation would be to throne to a show. Boston has a thriving music scene with venues of all shapes and sizes. I unchangingly trammels Jambase to see who’s playing in a municipality when I travel.

Perhaps you just want to nippy 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 skills here that they don’t plane have a menu. Drinks are created expressly for your taste with the freshest ingredients. 

Your weekend in Boston can moreover come full whirligig if you throne over to 21st Amendment. If you’re not well-versed in US history, the 21st summons 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.

Weekend in Boston for Foodies (top 5 experiences)

Weekend in Boston for Foodies

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

1. North End Walking Supplies Tour – Eat your way through Boston’s North End (Little Italy) and discover pure spots to eat. Sample meats and cheese in the oldest Italian Salumeria in Boston, visit an Italian bakery, and more. Find out increasingly here.

2. North End Little Italy Pizza Tour – A pizza-forward tour that you won’t want to miss! If you’re into sampling some of the weightier pizzas the North End has to offer, this one is for you. Learn increasingly here.

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

4. Seafood and History Walking Tour – Feast on a tasty lobster roll, clam chowder, fresh oysters, jumbo shrimp, and more. Enjoy the supplies while walking virtually Boston with your guide and learning the history of the city. It’s well-nigh a 2.5-hour experience. Find out increasingly here.

5. Brewery Tour with Lunch – On this fun brewery tour, you’ll visit cider houses, breweries, and distilleries, while sampling drinks at all of them. Lunch or dinner is included (depending on which time of day you book) as well as transportation. Learn increasingly here.

Insider’s Tips for a Weekend in Boston

Tips for a Weekend in Boston

I hope you have an superstitious time in Boston with the help of this itinerary. I’m sure you’ll have an plane largest one if you follow these tips as well, all of which served me well on my mythological visit to Boston:

Skip the winter – This itinerary is weightier suited for the warmer months. It won’t be nearly as enjoyable in the often stormy unprepossessed Boston winter. 

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

Check the calendar – There are lots of big events going on in Boston throughout the year. It’s weightier to trammels the timetable 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 upturned trying to pull off this itinerary.

Talk to the locals – This applies everywhere you travel, but I finger like I need to make it a point here. I only spent a weekend in Boston but had several unconfined conversations with locals. They’re enthusiastic well-nigh sharing translating and recommendations for their city, and plus you get to hear the superstitious Boston accent. 

Go to a game – I know not everyone is interested in sports, but this municipality is incredibly passionate well-nigh its teams. This is expressly true of the Red Sox. Do your weightier to make it to a game, or at least prod into a local sports bar if you can’t snag tickets. 

Getting Virtually Boston

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

It’s located in East Boston just a few miles from downtown. You have a few variegated options for how to get there.

Private Charter Bus

GoGo Charters in Boston is a visitor that offers a fun and practical way to get virtually the city. If you’re visiting Boston with a group of people, why not rent your own minibus, or full-sized bus to take you around?!

Whether you’re traveling to Boston for a stagette or stag party, a corporate event, a family reunion, or just a fun getaway with a group of friends, having a bus is a unique mode of transportation.

See all the sights in Boston in style, and don’t worry well-nigh drinking or driving when you throne out for the night. Check out GoGo Charters and get a self-ruling quote.

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. Weightier of all, it’s totally free! Those staying in other areas can use a self-ruling transfer to the Red Line as well.

It’s moreover 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 self-ruling bus ride.

For a detailed squint at all the options, throne to the MBTA website.

By Taxi

Taxis are readily misogynist 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 virtually $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 widow to any trips to or from the airport. 

By Train and Bus

Boston is moreover hands reached via train or bus. In general, it’s easy to move up and lanugo the East Coast and this is expressly true between the big cities.

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

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

Where to Stay With 2 Days in Boston

Boston In 2 Days: Your Perfect Weekend Itinerary In 2024

In the interest of convenience and comfort, it’s weightier 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 hands use the self-ruling airport bus and probably just walk to your accommodation. I don’t know well-nigh you, but I want to spend increasingly time exploring and less time in traffic. Boston in 2 days is doable, just make sure you segregate walk-up in a good location. 

Staying downtown moreover 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 moreover easy to wangle places like Harvard and Fenway Park via public transportation. There are plenty of unconfined options for places to shop, eat, drink, and stay here as well. I stayed downtown during my visit there, and I strongly recommend you do to.

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

  • Budget: HI Boston (Hostelling International)
  • Mid-Range: Omni Parker House
  • Luxury: Four Seasons 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. When Bay is moreover a fun zone to stay in for its proximity to Newbury Street and Fenway. 

FAQs for a Weekend in Boston

Here are answers to some commonly asked questions well-nigh spending a weekend in Boston.

Is Boston a fun place for a weekend trip?

Absolutely! With historic landmarks, natural beauty, spanking-new (often seafood-based) cuisine, and a thriving bar and brewery scene, Boston is a whole lot of fun for a weekend trip.

Is 2 days in Boston enough?

Full of attractions and landmarks, Boston’s meaty municipality part-way ways that you can wits a lot in only 2 days. From history to nature to food, there’s plenty to enjoy in Boston on a 2-day trip.

What is the weightier month to visit Boston?

The weightier time to visit Boston is from June to September. Sidewalk cafes are open, baseball season is on, and the unprepossessed of winter hasn’t yet set in.

Is Boston unseemly or expensive?

There’s no doubt that Boston is an expensive city, though not as expensive as NYC, making it a good volitional to the Big Apple.

What is Boston known for?

Boston is known for the Red Sox and Fenway Park, the Boston Marathon, top universities (Harvard, MIT, etc.), important events in American History such as the Boston Tea Party, iconic seafood dishes, and the bar from Cheers (among many other spanking-new watering holes).

Enjoy Your Weekend Trip to Boston

While 2 days in Boston isn’t really unbearable time to get under the skin of the city, it’s certainly a nice introduction. I felt like I got a good finger for the municipality and had been in Boston for much longer than just a weekend.

I’m sure you’ll have the same thought that I did, and that is “I’ll just have to come when 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 wool wham with my weekend in Boston, soaking up the history on the Freedom Trail, digging into a big ole’ trencher of clam chowda, and cheering for the Sox (which was tough as a Tigers fan, believe me), and more.

Should you come when from your trip to the municipality with any spanking-new recommendations of your own, please waif a scuttlebutt unelevated and let us know. I hope you enjoyed this 2 day Boston itinerary.