Boston in 2 Days: Your Perfect Weekend Itinerary

Are you looking for the perfect What to See in Boston in 2 Days itinerary? I recently returned from Boston and I’ve got the best things to do here.

Boston is a city steeped in history, with a vibrant culture and a food scene that is second to none. If you only have a weekend getaway to Boston or 2 days to explore this incredible city, fear not. I recently visited Boston for the third time and found that I could see many of the things I wanted to see. By staying downtown and armed with an attractions pass, I was able to hit all the highlights of Boston in 2 days, including return visits to some of my favorite spots. 

I’ve done Boston on my own, and with each of my children on separate trips. Each time it’s been about 2 days in Boston to see the highlights.

With a well-planned itinerary, you can see and do the most important things, while still experiencing the city’s charm and character. In this post, I’ll share with you a perfect itinerary for spending two days in Boston.

Day 1 Boston Itinerary

Before you set out on your 2 Day Boston Itinerary, I’d recommend an all-inclusive Go City Boston card. Many of the below are included in the pass and the savings are well worth it.

Breakfast in Boston

To start your day, head to one of Boston’s fantastic breakfast spots. Some popular options include Flour Bakery, Tatte Bakery & Cafe, and The Friendly Toast. All of these offer delicious breakfast options and are located throughout the city. Flour Bakery and Tatte Bakery are close to Boston Common. 

Boston Common

After breakfast, head to Boston Common, the oldest public park in the United States. It’s a great place to start your tour of the city, and you can easily spend an hour or two wandering around the park’s 50 acres. You’ll see the Soldiers and Sailors Monument, the Parkman Bandstand, and the famous Frog Pond.

My new favorite attraction in Boston Common is The Embrace, a bronze sculpture representing an embrace between Martin Luther King, Jr, and Coretta Scott King. The sculpture is over 20 feet tall and formally dedicated on January 13, 2023. 

Boston Public Garden

Next, head to Boston Public Garden, which is located right next to Boston Common. This park is famous for its beautiful flowers, swan boats, and its famous statues. One of the most iconic sights in the park is the Make Way for Ducklings sculpture, which was created in honor of the popular children’s book of the same name.

Cheers

No Boston weekend trip to is complete without a stop to the Cheers sign and even the pub below. One of the top Boston things to do, the Cheers sign is right across the street from the Boston Public Gardens. With the surrounding area’s cobblestone streets, old-style buildings and lush greenery, you can feel like you’re taking a step back in time.

The Bull and Finch Pub in Boston, Massachusetts, was established in 1969. It quickly became a local favorite among the college students from nearby colleges as a place to relax and socialize after class.

In 1982, the Bull and Finch gained national fame when it became the inspiration for the television show “Cheers,” which ran for 11 seasons. In 2002, the exterior of the pub was given an iconic sign of its own, featuring the show’s logo – a beer stein with a foaming head.

Since then, tourists have flocked to this popular spot to get their photo taken in front of the Cheers sign and experience one of Boston’s most famous landmarks. To this day, visitors can still grab a bite or a pint at The Bull and Finch, where everyone is still treated like family.

Swan Boats

While you’re in the Boston Public Garden, be sure to take a ride on the famous Swan Boats. These boats have been a Boston tradition since 1877 and are a great way to see the park from a unique perspective. Note these are only available in the warmer months. When I visited in March, the pond was drained. 

I was glad to return in the summer with my daughter and take a delightful trip around the pond.

Brattle Book Shop

One unique destination that bibliophiles won’t want to miss is the Brattle Book Shop.

This beloved bookstore has been a staple of Boston’s literary scene since 1825, and it’s filled with rare and used books of all genres. The shop’s outdoor sale lot is also a must-visit, where you can browse through bargain books and antique prints.

Located on West Street not far from Boston Common, the Brattle Book Shop is a wonderful place to spend an afternoon perusing the shelves and discovering new literary treasures.

If you have a weekend trip to Boston, hit this on Saturday. They are closed Sundays.

Freedom Trail

After your swan boat ride, it’s time to explore the Freedom Trail, a 2.5-mile route that takes you through 16 historical sites that are significant to the American Revolution. The trail is marked with a red line, so it’s easy to follow. Along the way, you’ll see some of the most famous historical sites in the country, including the Massachusetts State House, Granary Burying Ground, and the Old South Meeting House.

You can easily walk this trail on your own and at your own pace, to discover the historical sites along the trail. For those looking to dive deeper into Boston’s rich history, I highly recommend taking a guided Freedom Trail walking tour.

You can choose any tour out of the visitors center in Boston Common. If you have a Go City Explorer or All-Inclusive pass, choose the Official Freedom Trail Tour. This includes a knowledgeable guide dressed in colonial attire who will regale you with stories of Boston’s role in the American Revolution, from the Boston Tea Party to the Battle of Bunker Hill.

A guided tour is an excellent way to learn about the city’s history and culture while taking in some of its most famous landmarks.

Buy the Go City Explorer Pass to get the Official Freedom Trail Tour here. ➡️

Boston Massacre Site

One of the most significant sites on the Freedom Trail is the site of the Boston Massacre. This event, which took place on March 5, 1770, was a key moment in the lead up to the American Revolution. Today, you can visit the site of the massacre, which is marked with a plaque.

Old South Meeting House and Old State House

Continuing along the Freedom Trail, you’ll come to the Old South Meeting House, which was where the Boston Tea Party was planned. Next, head to the Old State House, which was the site of the reading of the Declaration of Independence.

These two locations offer a combo pass where you can enter and learn more about what happened at those locations. If you do not do a guided Freedom Trail Tour, stop in to get the history behind these locations, including information and renderings of the Boston Massacre.

King’s Chapel

King’s Chapel is a historic church located in the heart of downtown Boston. Built in 1686, the church is one of the oldest buildings in the city and has a rich history that spans more than three centuries. The chapel’s unique architecture, with its simple exterior and ornate interior, reflects the changing styles and influences of the times in which it was built.

Adjacent to King’s Chapel is the King’s Chapel Burying Ground, one of the oldest cemeteries in Boston. Established in 1630, the burying ground contains the graves of many of Boston’s early settlers, including John Winthrop, the first governor of the Massachusetts Bay Colony, and Mary Chilton, one of the Mayflower Pilgrims.

I couldn’t get enough of visiting the old cemeteries in Boston and 4 are within a decent walk.

Visitors to King’s Chapel can take a guided tour to learn about the history of the church and the burying ground, as well as explore the many exhibits and artifacts on display.

Whether you’re a history buff or simply looking to experience one of Boston’s most iconic landmarks, King’s Chapel and the adjacent burying ground offer a unique and fascinating glimpse into the city’s colonial past.

Faneuil Hall Marketplace

After all that history, it’s time for a little shopping. Head to Faneuil Hall Marketplace, which is a historic shopping district that dates back to the 1700s. You’ll find a wide range of stores and restaurants here, as well as street performers and musicians.

Quincy Market for Lunch in Boston

While you’re in Faneuil Hall Marketplace, be sure to check out Quincy Market, which is the oldest market in the country. It’s a great place to grab lunch, with options ranging from seafood to sandwiches to pizza.

Paul Revere House

After lunch, head to the Paul Revere House, which is located in the North End. This historic house was built in 1680 and is the oldest building in downtown Boston. It’s also the home of Paul Revere, one of the most famous figures in American history.

Old North Church

Next, head to the Old North Church, which is another significant site on the Freedom Trail. This church played a crucial role in the American Revolution, as it was here that Paul Revere famously hung his lanterns to signal that the British were coming by sea.

Our guide, from the Freedom Trail Tour, portrayed himself as Samuel Prescott, who rode with Paul Revere. It was an engaging way to tell us about what went on in Boston during the years leading up to the revolution and include how history leaves out some equally important people. 

Copp’s Hill Burying Ground

While you’re in the North End, be sure to visit the Copp’s Hill Burying Ground, which is the second oldest cemetery in Boston. Many notable figures from Boston’s history are buried here, including several patriots from the American Revolution.

Some notable figures include Prince Hall, a Black abolitionist and founder fo Black Freemasonry.

Cotton Mather, of the Salem Witch Trials, is also buried here. 

Boston’s North End and Little Italy for Dinner

The North End is known for its Italian-American culture, and it’s the perfect place to grab dinner. There are plenty of great options, from classic Italian restaurants to modern gastropubs. Be sure to try some of the famous local dishes, like pasta with meatballs or a classic Margherita pizza.

Book this Boston North End Food and Walking Tour to sample the best in the area. 🍕

Canolis

Boston’s North End is known for its delicious Italian pastries, and two of the most famous bakeries in the area are Modern Pastry and Mike’s Pastry. 

While I was in the area, I conducted my own little taste test.

Modern Pastry has been serving up sweet treats since 1930, and its menu includes everything from cannolis to tiramisu to biscotti. The bakery is known for its high-quality ingredients and attention to detail, resulting in some of the best pastries in Boston.

Mike’s Pastry, founded in 1946, is another North End institution that’s famous for its cannolis. This bustling bakery offers a wide variety of flavors, including classic ricotta, chocolate chip, and limoncello. 

The lines at both places can be long, but the delicious pastries are well worth the wait. The lines move fairly fast, so don’t worry if it’s out the door. 

➡️ Keep in mind, both locations accept cash only! Don’t wait in a long line only to be turned away. I’d recommend at least $20.

While both bakeries are known for their cannolis, they each have their own unique specialties. 

At Modern Pastry, don’t miss the lobster tails, which are filled with cream and dusted with powdered sugar. And at Mike’s, try the lobster claw, which is made with almond paste and shaped like a lobster claw. No matter which bakery you choose, you’re in for a sweet treat that’s sure to satisfy your sweet tooth.

Overall, I thought they both tasted delicious and pretty similar. Cannoli’s at Modern Pastry are $5 and Mike’s Pastry is $5.50. Mike’s are slightly bigger. Honestly, pick one and you’ll enjoy it!

Drinks in Boston

After dinner, head to one of Boston’s famous bars for a nightcap. Sam Adams Brewery is a popular spot for beer lovers, while The Liberty Hotel offers a swanky rooftop bar with stunning views of the city. If you’re looking for something a little more low-key, The Last Hurrah is a classic Irish pub that’s been around since 1969.

For those interested in experiencing Boston’s pub culture, two historic watering holes worth visiting are the Bell in Hand and the Green Dragon Tavern.

The Bell in Hand, located on Union Street, is one of the oldest continually operating bars in the United States, dating back to 1795. This cozy pub has a lively atmosphere and is known for its selection of craft beers and signature cocktails, as well as its live music and trivia nights.

The Green Dragon Tavern, located on Marshall Street, is another historic pub that played a significant role in Boston’s revolutionary history. The tavern was a frequent meeting place for the Sons of Liberty, a group of patriots who opposed British rule in the colonies.

Today, the Green Dragon Tavern serves up traditional pub fare and has an extensive selection of beer on tap, including many local brews.

Both the Bell in Hand and Green Dragon Tavern offer a glimpse into Boston’s past while providing a fun and lively atmosphere for visitors. Whether you’re looking to enjoy a pint of beer or learn more about the city’s revolutionary history, these historic pubs are well worth a visit.

Another historic pub worth checking out is the Beantown Pub, located on Tremont Street. This cozy, basement-level bar has been around since the early 1900s and is known for its extensive selection of beers on tap and its delicious pub food.

The Beantown Pub is also famous for its unique location, as it’s situated directly above the historic Granary Burying Ground. Visitors can sip a cold beer while looking out over the headstones of some of Boston’s most famous residents, including Paul Revere and John Hancock, and more importantly Samuel Adams. 

If you’re lucky your Freedom Trail Tour guide will point this location out, informing you this is the only place in the world to raise a cold Sam Adams, to a cold Sam Adams.

In addition to its great beer selection and unique location, the Beantown Pub is also a popular spot for sports fans, as it’s located just steps away from TD Garden, home of the Boston Celtics and Boston Bruins. Whether you’re in the mood for a cold beer, a tasty burger, or just want to soak up some of Boston’s rich history, the Beantown Pub is a must-visit destination.

Check out the Best Boston Hotels with Pools here.

Day 2 Boston Itinerary

Breakfast in Boston

Start your second day with a hearty breakfast at one of Boston’s classic diners. The Paramount is a great choice, with a menu featuring everything from omelets to pancakes to breakfast sandwiches.

Bunker Hill Monument

After breakfast, head to Charlestown to visit the Bunker Hill Monument, which commemorates the Battle of Bunker Hill. The monument is 221 feet tall and offers stunning views of the city from the top.

USS Constitution

The USS Constitution, also known as “Old Ironsides,” is a historic warship that played a significant role in the early history of the United States. Launched in 1797, the Constitution was one of the six original frigates authorized by the US Congress, and it saw action in the Quasi-War with France, the Barbary Wars, and the War of 1812.

Today, the USS Constitution is the oldest commissioned warship afloat in the world and is a popular attraction for visitors to Boston. The ship is open for tours, and visitors can explore its decks and learn about its storied history. In addition to the ship itself, the USS Constitution Museum, located nearby in the Charlestown Navy Yard, offers exhibits and interactive displays that provide a deeper understanding of the ship’s history and significance.

Visitors can also watch as the USS Constitution sets sail on her annual turnaround cruise, which typically takes place in July. During this event, the ship is taken out into Boston Harbor and turned around to ensure that its sails wear evenly. This tradition has been observed since the ship’s launch in 1797 and is a testament to the skill of the ship’s crew and the durability of the ship itself.

Whether you’re a history buff or just looking for a unique and memorable experience in Boston, the USS Constitution is a must-visit destination.

Boston Tea Party Ships

Next, head to the Boston Tea Party Ships, which is a museum that tells the story of the famous event that sparked the American Revolution. Visitors can board a replica of one of the tea ships and participate in a reenactment of the tea party.

The Boston Tea Party Museum, located on the Congress Street Bridge in the Fort Point Channel, offers visitors the opportunity to step back in time and experience one of the most significant events in American history. The museum features interactive exhibits and reenactments that bring the events of the Boston Tea Party to life, allowing visitors to experience the rebellion against British rule that helped to ignite the American Revolution.

Upon arrival, visitors are assigned a historical character to portray during their visit, adding a fun and interactive element to the experience. The museum also includes a replica of one of the ships involved in the original Tea Party, the Eleanor, which visitors can board and explore.

In addition to the museum exhibits, visitors can enjoy a tea-tasting experience, sample colonial-era treats, and learn about the importance of tea in colonial society. The museum gift shop offers a wide selection of unique and historically inspired souvenirs, including tea blends and commemorative items.

Whether you’re a history buff or just looking for a fun and interactive experience in Boston, the Boston Tea Party Museum is a must-visit destination. The museum provides a unique and immersive way to learn about one of the most significant events in American history and is a great way to experience Boston’s revolutionary past.

Book your Boston Tea Party Ships and Museum here 🫖 ⚓️

Lunch in Boston

For lunch, head to one of Boston’s seafood restaurants and try some of the city’s famous clam chowder or lobster rolls. Some great options include Union Oyster House, Legal Sea Foods, Neptune Oyster, and Yankee Lobster Co.

Beacon Hill

After lunch, head to Beacon Hill, which is one of Boston’s most historic and picturesque neighborhoods. Take a stroll down Beacon Street and admire the beautiful brownstone buildings, or visit Acorn Street, which is one of the most photographed streets in the city.

Boston is known for its beautiful tree-lined streets, and there are plenty of them to explore in Beacon Hill and the surrounding neighborhoods. Commonwealth Avenue, Newbury Street, and Marlborough Street are all great options.

Fenway Park

No visit to Boston is complete without a trip to Fenway Park, the home of the Boston Red Sox. If there’s a game happening during your visit, be sure to grab tickets and experience the energy of one of the oldest ballparks in the country.

Fenway Park is one of the most iconic landmarks in Boston and is home to the Boston Red Sox baseball team. Located in the heart of the city, Fenway Park has been hosting baseball games since 1912 and is the oldest ballpark in Major League Baseball.

With its unique features, including the famous Green Monster wall in left field and Pesky’s Pole in right field, Fenway Park has become an important symbol of Boston’s sporting and cultural heritage. Visitors can take a guided tour of the ballpark to learn about its history, see the field up close, and explore the many exhibits and memorabilia on display.

In addition to baseball games, Fenway Park hosts a variety of events throughout the year, including concerts, festivals, and other sporting events.

With its rich history, unique architecture, and exciting atmosphere, Fenway Park is a must-visit destination for anyone visiting Boston, whether you’re a die-hard Red Sox fan or simply looking to experience one of the city’s most iconic landmarks.

Book a tour of Fenway Park here 🏟️

Back Bay

After the game, head to Back Bay, which is one of Boston’s most upscale neighborhoods. Here, you can explore the high-end shops and boutiques on Newbury Street or take a stroll along the beautiful Commonwealth Avenue Mall.

Boston Duck Tour

If you’re looking for a unique way to explore Boston, look no further than the famous Duck Tour! This amphibious tour takes visitors on both an hour-long land and sea tour of the city, so you can get the best of both worlds in one action-packed ride. On land, you’ll drive by historic sites like Beacon Hill, the State House, and TD Garden, while at sea you’ll take in sights like Christopher Columbus Park, the USS Constitution, and more.

Get your tickets today and experience a one-of-a-kind adventure with the Boston Duck Tour!

Boston Public Library

The Boston Public Library is one of the oldest and most beautiful libraries in the country. Visitors can take a guided tour of the historic building and see its stunning architecture, as well as browse its collection of books and manuscripts.

The Boston Go City Card has many of these attractions in their all-inclusive and explorer options. I’d highly recommend getting a 2-day All-Inclusive to maximize your time in Boston.

Dinner in Boston

For your final dinner in Boston, there are plenty of great options to choose from. The city is known for its diverse and delicious dining scene, with everything from classic American cuisine to international flavors. Some popular spots include Oleana for Mediterranean food, Toro for Spanish tapas, and Island Creek Oyster Bar for seafood.

Alternative Itinerary Ideas for Boston in 2 Days

If the above itinerary doesn’t suit your interests, there are plenty of other things to do in Boston. Or if you can extend and do a Boston itinerary of 3 days, consider these. Here are a few additional suggestions for your Boston two-day itinerary:

New England Aquarium

The New England Aquarium is a popular attraction in Boston, with a wide variety of marine animals on display. Highlights include the giant ocean tank, where visitors can see sharks, sea turtles, and other creatures up close, as well as the penguin exhibit.

Harvard University

Harvard University is located in nearby Cambridge and is one of the most prestigious universities in the world. Visitors can take a guided tour of the campus, which includes stops at Harvard Square, and historic buildings like the Widener Library and Harvard Yard.

Peabody Museum of Archaeology

The Peabody Museum of Archaeology is another great option for history buffs. The museum has an extensive collection of artifacts from around the world, including ancient Egyptian mummies, Native American art, and Mayan ceramics.

Museum of Fine Arts

The Museum of Fine Arts is one of the largest art museums in the country, with a collection that spans thousands of years and includes works from around the world. Highlights include the ancient Egyptian collection, the Impressionist gallery, and the American Wing.

Trinity Church

Trinity Church, located in the heart of Boston’s Copley Square, is quite the majestic symbol of American architectural brilliance. This Romanesque masterpiece mesmerizes visitors with its distinctive rusticated granite facade and intricate carvings.

Isabella Stewart Gardner Museum

Housed within a stunning Venetian-style palace, the museum’s intimate galleries showcase an eclectic array of masterpieces spanning centuries and continents. From priceless works by European masters like Titian and Rembrandt to exquisite Asian ceramics and textiles, each piece in the collection reflects Isabella Stewart Gardner’s discerning taste.

Beyond its impressive art collection, the museum’s lush courtyard garden offers a serene oasis, inviting patrons to linger and contemplate amidst verdant foliage and tranquil fountains.

Best Time to Visit Boston

The best time to visit Boston depends on your preferences and what you want to do while you’re there. The summer months (June-August) are the most popular, as the weather is warm and there are plenty of outdoor events and festivals happening. However, this is also peak tourist season, which means that prices can be higher and crowds can be larger.

If you’re looking for a quieter and more budget-friendly time to visit, consider coming in the spring (April-May) or fall (September-November). The weather is still mild, and there are plenty of things to do, from visiting museums to enjoying fall foliage.

Winter (December-February) is the least popular time to visit, as the weather can be cold and snowy. However, if you’re a fan of winter sports or holiday festivities, this can be a great time to visit.

Where to Stay in Boston

Boston has a wide range of accommodation options to suit all budgets and preferences. Some popular neighborhoods to stay in include:

Back Bay: This upscale neighborhood is known for its beautiful brownstone buildings and high-end shops and restaurants.

Beacon Hill: This historic neighborhood is one of the most picturesque in the city, with cobblestone streets and charming brick buildings.

Downtown: This is the heart of the city, with plenty of hotels, restaurants, and attractions within walking distance.

Read my review of the InterContinental Boston. it was a perfect place to stay no more than 15 minutes from many of these attractions.

Cambridge: If you’re visiting Harvard University or MIT, staying in nearby Cambridge can be a good option. This neighborhood is also known for its lively nightlife and cultural events.

Getting Around Boston

Boston is a walkable city, and many of the main attractions are within walking distance of each other. However, if you need to travel further, there are plenty of transportation options available. The subway system (known as the “T”) is a convenient and affordable way to get around, with multiple lines and stops throughout the city. You can purchase a CharlieCard or CharlieTicket to pay for your fare, and fares vary depending on the distance you’re traveling.

In addition to the subway, Boston has a bus system and a commuter rail system that connects the city to surrounding suburbs. Taxis and ride-sharing services like Uber and Lyft are also widely available.

Final Thoughts: 2 Days in Boston Itinerary

Boston is a vibrant and historic city with plenty of things to see and do. Whether you’re interested in history, and culture, or just exploring new neighborhoods, there’s something for everyone in this charming city.

If you only have a weekend in Boston, be sure to prioritize the highlights, including the Freedom Trail, Boston Common, the North End, and Beacon Hill. Don’t forget to indulge in some local cuisine, like clam chowder, lobster rolls, and cannolis.

Is 2 days in Boston enough? It is for the highlights, but like any city, more time is always better to get the maximum experience.

If you have more time, there are plenty of other things to do and see in Boston, from visiting the New England Aquarium to exploring the city’s many museums and galleries.

No matter what you choose to do in Boston, you’re sure to fall in love with its unique blend of history, culture, and modern charm.

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