Weekend in Boston: A Great 2 Day Boston Itinerary

Granted, 2 days in Boston is not enough time to see and do everything that this great city has to offer, but you can definitely cover some serious ground.

The weekend in Boston itinerary below will have you visiting some of Boston’s best historical sites, eating some great food, and touring some of Boston’s best neighborhoods.

Boston is one of the most historic American cities you can find.

Combine that with the fabulous food scene, great outdoor spaces, and beauty of the city, and it is no wonder that Boston continually makes the list of best cities to visit in the United States.

Exploring Boston in just 2 days will be fast and furious.

Don’t worry; it will be worth seeing as much of this famous city as possible during your time here!

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Getting to Boston

If you are flying into Boston, you will arrive at Logan International Airport (BOS).

This is a major international airport with connections to cities and countries worldwide.

Logan International Airport is located just east of the city, making Boston easily accessible.

Once you arrive at the airport, you can enter the city, including shared rides, the “T,” taxi, train, or bus.

We found the public transportation system in Boston reliable and easy to navigate.

I recommend trying out public transportation for these reasons (and to save a little money).

MTBA (the “T”)

The Massachusetts Bay Transit Authority (the “T”) is the most economical way to get from the airport to the city.

If you stay in Downtown Boston, the silver line will take you to the South Station completely free!

Don’t worry if you aren’t staying downtown; you can do a free transfer to the red line to continue your journey.

For more information, check out the MTBA website.

Rideshare

Both Uber and Lyft operate throughout Boston, making it quick and easy to grab a ride anytime.

Be careful of surcharges during peak times, as these can add up quickly.

Taxi

Of course, you can always take a taxi from the airport.

There is no “flat rate” option, so be cautious if taking a taxi.

Make sure that you are following the route on your phone and that the driver uses the meter so you can see what you are being charged.

Train or Bus

Boston is well served by several train and bus routes as well. These routes serve most of the big cities on the East Coast, including Boston, New York City, Philadelphia, and Washington DC.

If you choose to travel by train or bus, booking your ticket early can save you tons of money.

Where to Stay for a Weekend in Boston

For our Boston trip, we stayed in the downtown area of Boston.

This area felt very safe, and many significant attractions were within walking distance, meaning we had more time to explore the city!

We loved staying at the Courtyard by Marriott Downtown/North End.

Our hotel was modern, clean, and very spacious.

In addition, it was literally one block from Boston’s North End (aka Little Italy), the historic district loaded with fabulous eateries!

Downtown lets you be close to the Freedom Trail and the Waterfront, so you can easily experience the best of Boston.

The downtown area is also well-served by public transportation, making it convenient to get around the city if you don’t want to walk.

Here are a few of our recommendations for where to stay for your 2 days in Boston itinerary.

• Budget: Revolution Hotel Boston
• Mid-Range: Courtyard by Marriott Downtown/North End
• Luxury: The Liberty Hotel Boston

If you don’t want to stay downtown, then you can also search the Back Bay and Waterfront areas for hotels.

When to Visit Boston

Spring is the optimal time to visit Boston.

The weather is nice, and most college kids go home in May, making the city less crowded.

The spring also brings blossoming tulips, festival season, and excellent patio weather.

Fall is another great time to visit Boston.

The air turns cooler, and the trees show off their beautiful fall colors.

This makes fall a great time to explore the city on foot and take in the sounds and sights of Boston.

Honestly, I would avoid a weekend in Boston during the winter.

It is too cold for me to spend 2 days in Boston this season!

Read Next: 25 Fun Things to do in Salem, MA

Day 1 in Boston Itinerary

For our weekend in Boston, we will kick off our adventure by diving into the many historical sites around town.

Don’t worry, though; there will be plenty of opportunities for shopping, yummy meals, and even some time to relax.

Boston Common & Boston Public Garden

The Boston Common and the Boston Public Garden are located next to each other, so it only makes sense that we include them together.

This is the oldest park in the United States, so it makes perfect sense to start our 2 days in Boston itinerary here.

The Boston Common dates back to 1634 and has been a meeting place for activists throughout history, including the American Revolution, the Civil Rights Movement, and anti-Vietnam War rallies.

As you walk around the park, you will notice several statues and monuments.

Several of these are very interesting reads.

Take note of the Massachusetts State House across the street from the park.

The Massachusetts State House is now the seat of the three branches of the Massachusetts government, but it used to be the site of the Hancock mansion.

Right next to the Boston Common is the Boston Public Garden. You can’t miss this park as it is home to the fun swan boats!

Of course, there are several areas for you to relax and unwind in the garden.

The Boston Public Garden also carries significance, as it was the first botanic garden in the United States.

These two green spaces are a great respite from the hustle and bustle of the city.

In addition to this, the Freedom Trail is part of the Boston Common, so this is a great starting point for our next activity, the Freedom Trail.

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The Freedom Trail

Boston’s Freedom Trail is a 2.5-mile trail that connects many national historic sites throughout Boston.

These sites include museums, burying grounds, churches, parks, and more, all instrumental in starting the American Revolution.

To get the most out of the Freedom Trail, we recommend taking a guided tour.

The tour guides are knowledgeable and can give you insight into the sites you wouldn’t usually know.

If you would rather make the Freedom Trail at your own pace, consider downloading an audio tour.

We did this during our time in Boston, and we enjoyed going at our own pace.

You have already seen two sites on the Freedom Trail, the Boston Common, and the Massachusetts State House.

As you continue along the city’s red brick trail, you will come across several other historical sites, some of which we highlight in more detail below.

Honestly, the Freedom Trail is a must-do during your time in Boston. I mean, it is one of the best things to do on the east coast of the US for a reason!

Old South Meeting House

The Old South Meeting House is one of the stops along the Freedom Trail and is one of the most significant buildings in American history.

This is where the Boston Tea Party began. Not only that, but it was also here that the United States started its first historic conservation efforts.

Throughout history, many noteworthy members of the Old South Meeting House have been, including Samual Adams, Phillis Wheatley, and Benjamin Franklin.

The Old South Meeting House has also been the site of many public protests, the most significant being the tax debate on December 16, 1773.

After failed compromise, Sam Adams and the Sons of Liberty marched down to the Boston Harbor and dumped 342 chests of tea into the harbor.

This historical event, known worldwide as The Boston Tea Party, signaled the beginning of the American Revolution.

There is a fee to go inside the Old South Meeting House.

Old State House

The Old State House is one of Boston’s oldest surviving public buildings.

Right outside the Old State House, the Boston Massacre occurred in 1770.

Entry to the Old State House is free. Some noteworthy artifacts include John Hancock’s red velvet coat and tea salvaged from the Boston Tea Barty.

Faneuil Hall

Referred to as the “Cradle of Liberty” since the first town hall meeting in America occurred here.

Later, the hall became would play an integral role in the American Revolution. Faneuil Hall is free to enter and is worth a stop if you are a history buff.

Take note of the golden grasshopper weathervane atop the building and ask the story behind it.

If you are hungry for lunch or want to do some shopping, this area is perfect for that, also.

Visit the other historic building on the property to take in all this area offers.

Paul Revere House

The Paul Revere House is in the vibrant North Boston neighborhood of Little Italy.

Paul Revere owned the house from 1770-1800, and it is the oldest remaining structure in downtown Boston.

This is the only home that is along the freedom trail as well.

During your Boston weekend, you can tour the house (for a fee) if you would like.

Honestly, I didn’t think it was worth the entry fee.

Old North Church

The Old North Church is another significant building in American history.

Built in 1723, this is Boston’s oldest church.

Of course, if it is on the Freedom Trail, you know it also has historical significance.

For it was here that Paul Revere placed the lantern, signaling that the British were coming. “One if by land and two if by sea.”

You can take a self-guided tour of the church during your weekend in Boston to see the interesting box pews and the 1759 organ.

In addition, you can also visit the crypts below the church on a guided tour to learn about the burial practices of the church throughout history.

We found the church and crypt tour to be very interesting and informative. Therefore, we highly recommend it.

USS Constitution

The USS Constitution is the oldest commissioned warship that is still afloat today.

Launched in Bostin in 1797, the boat has quite a maritime history.

During the War of 1812, the British cannonballs were said to be bouncing off the ship, giving it the name “Old Ironside.”

Visitors are welcome to come aboard the historic vessel to tour the boat and see what life at sea was like for the sailors that called it home.

Even active-duty military men and women are on board to answer your questions and give you more information about the boat.

Honestly, this site has to be on your 2 days in Boston itinerary.

It is such an interesting piece of history and worth your time on your weekend in Boston.

Bunker Hill Monument

The final stop on the Freedom Trail is the Bunker Hill Monument. This monument commemorates that the first battle of the Revolutionary War was fought right here on Bunker Hill.

There is also a museum across from the monument that you can add to your Boston itinerary if you like. There are artifacts from the battle and a few other items.

Honestly, this site is a little out of the way. I would skip it unless you are just a super Revolutionary War enthusiast.

Explore Boston’s North End

The North End neighborhood, known as “Little Italy,” is Boston’s oldest neighborhood.

This charming neighborhood houses some fabulous Italian restaurants and bars, making it the perfect place to end the first day of your Boston itinerary.

I don’t know if you could go wrong with any North End restaurants, but a few are highly recommended.

One of these restaurants is La Famiglia Giorgio’s.

This popular Italian restaurant gets crowded, so make reservations early if your heart is set on eating here.

After dinner, you must get dessert from Mike’s Pastry and Modern Pastry.

Both have a wide variety of delicious Italian treats for you to enjoy, but you have to do one thing, get a cannoli from each.

These two establishments in Boston’s Little Italy have had a friendly competition for years to determine who has the best cannoli in the North End.

Try them for yourself, and see which one gets your vote.

We loved them both, but Modern was our winner. Modern Pastry beat out Mike’s Pastry, in our opinion, because

Take a stroll around Boston’s Little Italy to walk off some of that great food you just ate.

Take in the historic cobblestone streets and the fabulous architecture of this area.

If you aren’t worn out yet, tonight is a great night for a ghost and graveyard tour in Boston! These tours are a fun way to learn about the area’s history.

Read Next: 30 Fun Day Trips From Boston

Day 2 of Your 2 Days in Boston Itinerary

Today you have a choice for your Boston itinerary.

For those still wanting more of Boston’s history, we recommend visiting the Boston Tea Party Ships and Museum.

Done with historical sites?

Then consider checking out one of the many fine museums in the city.

With that in mind, let’s dive into your choices for day 2 of your 2 days in Boston itinerary.

Boston Tea Party Ships and Museum

The Boston Tea Party Ships and Museum allow guests to become immersed in the events leading up to the American Revolution.

The Boston Tea Party Museum is a unique museum experience located in the Seaport District.

Guests are invited to the interactive museum to explore the events leading up to the monumental historical event.

For an hour, visitors are guided by a costumed host visiting the museum and then being led out to board the 18th-century ships and dump tea in the Boston harbor! (I told you this was a unique museum!)

Granted, the ships are full-size replicas of 18th-century vessels, but they are still cool!

The Boston Tea Party Ships and Museum must be on your list of things to do during your Boston weekend.

Museum of Fine Arts

If you choose to skip the Boston Tea Party Museum, you might want to add the Museum of Fine Arts to your 2 days in Boston itinerary instead.

The fifth-largest museum in the world, The Museum of Fine Arts in Boston houses almost half a million artworks displayed in over 100 galleries.

The art in this Boston museum is from all over the world, including Asia, the Americas, Europe, Africa, and more.

Don’t miss the gorgeous and serene Japanese garden during your time at the Museum of Fine Arts.

This beautiful garden named the “Garden of the Heart of Heaven” is the perfect place to find peace from the city during your 2-day itinerary in Boston.

You could easily spend a whole day in Boston here, so pace yourself accordingly since you only have 2 days in Boston!

Isabella Stewart Gardner Museum

You might want to add the Isabella Stewart Gardner Museum to your weekend in Boston.

Located in the gorgeous Back Bay neighborhood, this museum houses an expansive art collection worldwide.

Not only is the house, which is modeled after a Venetian palazzo, a work of art but so is the gardens.

Be sure and learn about the infamous art theft that occurred here also.

The theft that occurred here is said to be the largest art heist in history when in 1990, 13 pieces of art were stolen.

If you want to learn more about the art heist, watch the Netflix movie This is a Robbery: The World’s Largest Art Heist.

After watching the movie, you might be unable to resist adding this museum to your Boston weekend.

Museum of Science

Another excellent museum choice to consider during your 2 days in Boston is the Museum of Science.

Not only is the Museum of Science a fun, interactive science museum, but it also houses an indoor zoo!

Located on a plot of land that spans the Charles River, the Museum of Science will immerse you in Science in no time.

Visitors can enjoy IMAX films, Planetarium shows, and more than 700 interactive exhibits.

This is a great addition to your weekend in Boston itinerary if you visit Boston with children!

Back Bay and Newbury Street

The Back Bay area of Boston is a popular dining and shopping district.

Begin your exploration at Copley Square. Copley Square is a public square that has been a long-time meeting place for the people of Boston.

In the early to mid-1800s, Copley Square was known as the ‘Art Square’ because of the many cultural institutions that surrounded it.

Experts say that Copley Square contains some of the best historical buildings in Boston, so you must add this to your weekend in Boston itinerary.

The architecture of these buildings alone is enough to make you want to visit!

Surrounding the square, you will find the Old South Church, Trinity Church, and the Boston Public Library.

The Old South Church started in Boston in 1670 and is still an active congregation.

Consider taking this guided tour to learn more about the Back Bay area.

Boston Public Library

According to the Boston Library’s website, this library houses more than 23 million items!

Of these, over 1.7 million are unique manuscripts and rare books.

This expansive collection of materials ranks this library third-largest in the United States.

Books are not the only items housed in the library.

There is also a vast collection of paintings, historical artifacts, and original music. Some are from the likes of Mozart, Rembrandt, and Shakespeare.

Even if you don’t want to settle into a cozy chair and read a book, the Boston Library is worth visiting during your Boston weekend.

The architecture of the building alone will leave you speechless.

Newbury Street

Newbury Street is a shopper’s paradise!

This 8-block stretch of road has boutique shops, art galleries, salons, fun bars, and fabulous restaurants.

Looking around, it is hard to believe that this area used to be the Boston Harbor!

It wasn’t until 1857 that Boston began filling this area to allow for the expanded growth of the city.

The project was completed around 1882, and the building began.

These are the buildings you still see today.

The beautiful European architecture gives this neighborhood the reputation of being the prettiest area in Boston.

Today you can shop ’til you drop at the many name-brand and boutique stores that call this area of Boston home.

When you need a break, pop into one of the coffee shops or restaurants that line the streets here also.

Shoppers and history enthusiasts definitely need to have the Back Bay area on their Boston weekend itinerary.

Fenway Park

To round out our 2 days Boston itinerary, let’s visit the iconic Fenway Park.

A visit to Fenway Park should still make your list, even if you aren’t a baseball fan.

The Fenway Park area in Boston is known to have a thriving nightlife even if there isn’t a game going on at the park.

Locals and visitors flock to this area for entertainment, bars, and restaurants around the park.

Of course, if you are a baseball fan, try to plan your visit to Fenway Park when a game is happening.

This will ensure that you get the whole experience during your time in Boston.

Don’t forget that Fenway offers guided tours of the park as well.

These tours are a great way to learn more about the history associated with this iconic park.

Making this a perfect addition to your weekend trip.

Check here for available tours:

Boston Harbor Walk

If you don’t want to visit Fenway during your weekend trip, consider doing the Boston Harborwalk instead.

The Boston Harborwalk is a 43-mile near-continuous park.

The Boston Harborwalk consists of over 40 parks, museums, beaches, restaurants, and retail facilities.

In addition to all of this, the Boston Harborwalk also hosts numerous festivities throughout the year.

I would say that this would be a great end to your weekend in Boston!

You might also consider taking a harbor cruise while in this area.

Have More Than 2 Days in Boston?

If you find some extra time in Boston (maybe you can make a 3 or 4 day itinerary), here are some other activities you may want to consider.

Boston Food Tour

Boston is famous for its food scene.

Boston has a great food scene, whether you are eating delicious Italian food (which we did A LOT) or chowing down on a famous lobster roll!

In our opinion, there is no better way to be introduced to a town’s food scene than to take a food tour.

We take a food tour in almost every major city (as we did in Boston)!

While there are many food tours, if Secret Food Tours offers a tour, we always choose them.

Secret Food Tours is a fabulous walking tour and a great addition to your trip to Boston.

You will walk around the iconic North End, exploring fabulous restaurants and learning about history.

This tour will have you eating everything from pumpkin ravioli to an authentic Boston lobster roll.

During your tour, there will also be a “secret food” that you get to sample. (I’m not telling you what it is….it’s a secret!)

Just know that this tour was one of the highlights of our trip to Boston, Massachusetts. I loved it so much that I would probably include it on my 2 day Boston itinerary!

Check out the food tours we have been on:

• Secret Food Tours Dublin
• Secret Food Tours Rome
• Savannah Food Tour
• Dallas Food Tour

Visit the Cheers Bar

The iconic television show Cheers was inspired by this bar in Boston.

Now, I must be honest; if you weren’t a huge Cheers fan, you could skip going inside.

You might want to take a picture with the sign instead.

For all of you die-hard Cheers fans, then you will enjoy visiting the iconic bar.

Inside, you can buy Cheers souvenirs, drink from a Cheers mug, and sit in ‘Norm’s chair.’

The pub-style food here is mediocre in taste, and the drinks were nothing special, in our opinion.

We still enjoyed the nostalgia of the place and had a great time during our visit to the Boston Cheers bar.

New England Aquarium

The New England Aquarium is a Boston public aquarium that is a world-class facility.

The Boston Aquarium is said to be the largest aquarium in New England and is a leader in marine research and preservation.

Visitors to the New England Aquarium can enjoy watching the animals up close and personal.

The aquarium is home to penguins, seals, octopuses, sea turtles, rays, sharks, and more.

As you walk around the aquarium, take in all the fabulous sites and sounds that make this aquarium such a unique attraction.

Harvard University

If you have extra time in Boston, why not head to the iconic educational institution, Harvard University?

You can walk around the campus anytime or take a guided tour.

Whatever tour you choose, Harvard University is a gorgeous campus with a fascinating history.

A tour here is an excellent addition to your weekend itinerary.

Take a Day Trip From Boston

Several fabulous areas surrounding Boston make for a great day trip if you have more than a weekend in Boston, Massachusetts.

Of course, one of the most popular day trips from Boston is to Salem, the ‘Witch City.’ Salem is a charming community full of intrigue and history and well worth being added to your Boston itinerary.

My history lovers will want to visit Lexington and Concord during their Boston trip.

Lexington and Concord are where the first shots of the Revolutionary War were fired.

The Plimoth Patuxet Museum is another historical site near Boston.

You can visit a living history museum celebrating the first Pilgrims in America here.

You can also visit the Cape Cod National Seashore in Boston. This seashore is known for its 40-mile-long stretch of beach surrounded by unique geography.

If you choose to visit Cape Cod, remember that you can take the fast ferry from Boston!

These are just a few suggestions for some great day trips from Boston.

Find the one you like best and take a little break from the city.

Food in Boston

Granted, we only scratched the surface of the amazing food scene in Boston.

Nonetheless, we ate some incredible food during our Boston trip. Here are a few of our favorite places:

Bell in Hand Tavern

The Bell in Hand Tavern was founded in 1793 and is credited with being America’s oldest tavern, making it a piece of American History.

While you could initially only buy ale at the Bell in Hand, that isn’t true today.

Today, the Bell in Hand has a full bar, a relaxed, historic atmosphere, and a great food selection.

We went for fish and chips during our visit, and it was delicious!

If you are into this type of establishment, you might consider taking the Historic Tavern Tour during your time in Boston!

Union Oyster House

Established in 1826, the Union Oyster House is another iconic Boston restaurant as it is considered America’s oldest restaurant.

Located on the Freedom Trail, the Union Oyster House is easy to find.

The interior alone is a reason to visit this restaurant. It is still arranged the way it was in 1826 when it served food to the locals, including Daniel Webster!

Since we aren’t huge fans of oysters, we went for the clam chowder, which was terrific.

They also serve delicious lobster rolls, crab cakes, and other seafood dishes.

Boston Public Market

Ok, I know that the Boston Public Market is not a restaurant; it is a collection of food stalls, but it still tops the list of places you should eat in the city.

The Boston Public Market was included on our food tour with Secret Food Tours, and we loved it so much that we went back on our own.

Marty had a delicious popover, and I had an amazing lobster roll.

This makes for a quick and easy food stop to add to your weekend getaway in Boston.

Quincy Market

We mentioned Quincy Marketplace when we were discussing the Freedom Trail.

If you didn’t stop to eat here, then do it now!

This historic marketplace opened to the public in the early 19th century as a place for locals to buy and sell fresh produce.

It has since transformed into the thriving market that you see in the city today.

Favorites from Quincy Market include clam chowders, lobster rolls, Boston cream pie (the official dessert of Massachusetts), and, of course, Bostonian baked beans.

Even if those don’t appeal to you, you can still visit as there are many other food choices!

Dumpling Cafe

If you are near Boston’s Chinatown neighborhood, run, don’t walk to the Dumpling Cafe.

Here you can eat dumplings until your heart is content. Try the Taiwan-style pan-fried dumplings!

Dunkin’ Donuts

I know Dunkin’ Donuts is a chain donut store, but you must visit at least once during your weekend getaway to Boston.

I mean, the popular donut store did originate here!

Omni Parker House

Another Boston original that must be on your itinerary is the Omni Parker House; why you ask?

Because this is where the famous dessert, the Boston cream pie, originated!

You can’t leave the city without trying this delicious dessert!

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