How To Spend 4 Days In Boston – Things To Do And See

Contrary to popular belief, Boston isn’t such a large city and it’s very easy to explore on foot. Some people consider it one of the country’s most beautiful and clean cities. For me, Boston is without a doubt one of the highlights on the East Coast, and it takes a high spot on my list of favorite cities.

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I’ve had the chance to visit Boston twice. The first time, I took a brief 2-hour walk downtown before a concert. The second time, this past summer, I decided it was finally time to return and spend more quality time there on my way to Cape Cod. Boston has so much to offer that I recommend staying for at least four days if this is your first time. This way, you can fully appreciate the city’s attractions and also explore some interesting places about 30 minutes away.

In this blog post, we’ll discover fascinating places to visit and activities to do in Boston for first-time visitors. Hang tight because there’s plenty to see in this beautiful city!

Boston Common and Public Garden

Just like New York has Central Park and San Francisco has Golden Gate Park, Boston has its own gems – Public Garden and Boston Common. While they might not match the size of New York and San Francisco’s large parks, they’re equally beautiful and fun. Located side by side, the Public Garden and Boston Common are the perfect urban retreat. With their ponds, open spaces, and historical landmarks, these two parks make the top of Boston’s must-see list for a reason. Stroll through the green spaces, take in the surroundings, or grab a snack and a drink and enjoy the waterside view.

In Public Garden check out the well-known:

• George Washington Statue 
• Make Way for Ducklings installation
• Edward Everett Hale Monument

In Boston Common check out the well-known:

• Boston Common Frog Pond
• Soldiers and Sailors Monument
• Brewer Fountain
• Parkman Bandstand

Massachusetts State House

Up the hill from Boston Common, within the charming Beacon Hill neighborhood, you’ll come across the Massachusetts State House. This magnificent building, besides serving as the state capitol, is also home to the governor’s offices and the Massachusetts General Court. Completed in the late 1700s, the State House of Massachusetts stands as an example of a Federal architecture masterpiece.

Winter St and Summer St

On the eastern edge of Boston Common, you can take a walk down the bustling Winter Street and Summer Street. These two pedestrian streets meet at a place known as Downtown Crossing, offering multiple retail options.

View Boston

To my surprise, there aren’t many places in Boston where you can enjoy panoramic city views from. Currently, the only observation deck available is “View Boston”, a three-floor experience that offers a remarkable 360-degree view of the city.

“View Boston” is located on top of the Prudential Center, the city’s second-tallest building. I was surprised how much more this experience was than I expected. There are two observation levels at “View Boston”- one of them is indoors and the second one is outdoors. Both provide complete 360-degree views.

Indoor and Outdoor

While on the indoor floor, you can check out the miniature representations of city buildings and learn more about them from virtual viewers positioned along the floor. The second level, named the Cloud Terrace, is outdoor and has a bar where you can grab a drink and enjoy the view from one of the tables.

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I am one of those people who always seek out a cool spot in a city where I can enjoy a breathtaking view from above. I would claim without a doubt that I have been to many observation decks so far. But what I really loved about “View Boston” was how much it had to offer compared to other observation decks. Throughout the floors, you’ll come across a few cameras for taking photos or videos, which later you will receive via email. When you download the pictures, you’ll get the opportunity to select from a range of background images. This photo opportunity, which many other places charge for (typically starting at $15-$20), is free here. You can snap a picture, add your own style, and download it without any cost. Print it out for a couple of bucks once you get home, frame it, and here’s your Boston souvenir!

Don’t miss the third floor of “View Boston” where you will find a light show of the city miniature along with other visual experiences.

Copley Square Park

Copley Square Park, located in the heart of Boston, is named after the painter John Copley. This square, with its charming fountain, makes a good break spot on a hot day. As you walk through the square, you’ll also come across Trinity Church, an Episcopal place of worship recognized as a National Historic Landmark. Just across from Copley Square you’ll find another church- the Old South Church.

Isabella Stewart Gardner Museum

Isabella Stewart Gardner, born in the late 1800s, was an American art enthusiast and a generous philanthropist. After her father’s death, Isabella inherited an impressive art collection, which gave a huge start to her art acquisitions. She also became the first American to own a painting by Botticelli.

The museum she established features an impressive collection of sculptures, paintings, decorative arts, and pieces of European, Asian, and American artworks. There is also a beautiful garden, offering picturesque views from all three floors. 

The Isabella Stewart Gardner Museum is also known for the biggest art theft in history. In March 1990, 13 masterpieces, collectively valued at over $500 million, were stolen and never found, despite the huge rewards offered.

Fenway Park

If you’re a baseball enthusiast or you’re just looking to soak in the thrill of a live game, make sure to visit Fenway Park, the home of the Massachusetts baseball team- the Red Sox. If you’re in search of some sports experience during the baseball season, Fenway is the place to be.

Newbury Street

Newbury Street, with its 120 stores and 60 restaurants, is a great spot for brunch, cocktails, dinner, or a shopping spree. This exciting entertainment district in Boston will captivate you with its beautiful architecture and vibrant colors. With a lot of pedestrian traffic throughout the day and the evening, Newbury Street is one of those places where you can truly immerse yourself in Boston’s atmosphere.

Commonwealth Avenue

Commonwealth Avenue is a long avenue that stretches through the city and makes a great walk between Fenway Park and Boston Common. Within these ten blocks, you’ll enjoy the beautiful Bostonian architecture and will encounter a few monuments and statues, including the Boston Women’s Memorial, Samuel Eliot Morison Sculpture, William Lloyd Garrison Memorial Statue, Boston Vendome Hotel Fire Memorial, General John Glover statue, and the Alexander Hamilton Statue. This long avenue offers an excellent option for a shady walk on hot summer days.

Post Office Square

Post Office Square is a small charming square in Downtown Boston. With a few benches and a small fountain, it’s a perfect spot for a brief pause while you explore this part of the city. Take advantage of the coffee shop at the corner, where you can grab a pastry and enjoy the shade.

Hungarian Memorial

Located right next to Liberty Square Park in Downtown Boston, the Hungarian Monument serves as a reminder of the historic events of the Hungarian Revolution and their significance. Officially known as the “1956 Hungarian Revolution Memorial”, the monument was built in 1986 to commemorate the 30th anniversary of the Hungarian Revolution.

Faneuil Hall Marketplace and Quincy Market

Surrounded by a dozen other attractions in the area, Faneuil Hall Marketplace and Quincy Market are heaven for people with spare time. Those two places offer numerous culinary choices and shops. A favorite spot for locals, especially on weekends, Quincy Market is the largest and oldest food hall in the country. It was created as an extended part of Faneuil Hall.

At the square just outside you can catch a glimpse of the Custom House Tower. For more market vibes, check out Boston Public Market just a couple of blocks away.

Boston Greenway / Rose Kennedy Greenway

I highly recommend walking along Boston Greenway. This 1.5-mile-long park stretches around the heart of the city and has multiple good spots to chill at. Make sure you check out Salem and Hanover Streets on the northern side of the park. Known as Boston’s Italian district, this area offers plenty of restaurants, shops, and landmarks. In fact, walking on Salem Street does feel pretty Italian. The street is quite narrow and it gives you a small Italian town vibe. With thriving bars, shops, restaurants, and captivating architecture, this neighborhood really made me feel like I was in Europe and turned my walk into a getaway from the usual American city streets.

On the left side of Rose Kennedy Greenway (the northern part of Boston Greenway), you’ll discover a cluster of bars, nestled on charming streets that very much remind you of a European town. While you’re in the area, make your way to the New England Holocaust Memorial, which features six glass towers, serving as a tribute to the 6 million victims of the Holocaust.

Old North Church

Built in 1723, The Old North Church is the oldest church building in Boston and one of its most iconic landmarks there. This symbol of the city is popular as part of the story of Paul Revere, a key figure in the American Revolution. In 1775, it was Revere who famously proclaimed “The British are coming!” in an effort to alert the colonists.

Visitors can book tours of the church, including a visit to its crypt. As you make your way to The Old North Church from Hanover Street, you’ll come across a horse rider monument and a fountain. This area is known as Paul Revere Mall and features a statue of Paul Revere himself, as well as The George Robert Fountain.    

Skinny House

This small charming building would barely catch your attention if you haven’t heard about it and you’re just walking around. Just a couple of blocks away from the Old North Church, the Skinny House is tucked in between other buildings and it has its own story.

Two brothers inherited the property but one of them was away at war and the other one took advantage of the situation by leaving his sibling with a really small part of the land. When the brother returned from war and saw what was left for him, he decided to build this tiny house for revenge and did it on the little land left. He wanted the small property to block the bigger one’s views and sunlight. The house became known as the “Spite House” and the name was even engraved at the front.

Back in 2021 the Skinny House was sold for $1.25 million.

Langone Park

Langone Park is a waterfront park situated in the northern part of Boston. It offers a baseball field and a playground to its visitors. Despite its prime location right by the water at the tip of the North End, this area was surprisingly quiet and I didn’t see more than five people while there. This actually worked out perfectly as I could use a short break from the city noise. The large wooden installations in Langone Park offer an ideal spot to relax, whether you’re just staring at the water or lying down with a good book.

Burroughs Wharf

I’m not sure if Burroughs Wharf is considered a hidden gem but during my visit it certainly felt that way. This waterfront sidewalk offers a gorgeous view and it’s a perfect escape from the bustling crowds. 

Christopher Columbus Waterfront Park

This public park in Boston was one of my favorites places visited. It’s no surprise since it’s right by the water and I always say “You’ll find me where the water is”. Christopher Columbus Waterfront Park, located in the North End, has a playground, green areas perfect for picnics, and stunning waterfront vistas. What more would you want from a park?

Long Wharf

Long Wharf serves as a main departure point in Boston and is also home to the Boston Waterboat Marina. You can take a seat on one of the benches and enjoy the view of ferries coming and going, as well as people strolling around to visit the few restaurants.

Just a short walk from Long Wharf, you’ll find Rings Fountain, a popular spot during hot summer days. With the Custom House Tower in the back, this square is a nice break spot while walking between the North End and the Waterfront.

New England Aquarium 

The New England Aquarium is a non-profit organization and home to a wide variety of aquatic animals among which California sea lions and African penguins. You will find it right next to Long Wharf.

Fan Pier Park

At the southern tip of the Waterfront, you’ll come across a bridge named Evelyn Moakley. Crossing this bridge will take you to one of my favorite spots in Boston, Fan Pier Park.

This charming park with its green spaces and a harbor walk provides a fantastic view of Downtown Boston. Be sure to walk all the way to the end and visit the Institute of Contemporary Art on the other side of the Fan Pier Marina. If you’re feeling hungry, consider checking out The Barking Crab restaurant. With a lively atmosphere, a variety of seafood options, and a beautiful city view, it was one of the highlights of my day.

Reflecting Pool at the Christian Science Plaza

This spot wasn’t initially on my list when I traveled to Boston, but while I was at the “View Boston” observatory, I noticed a massive surface of water and looked it up on Google. It was located right between the Prudential Tower and the Christian Science Center so I decided to go check it out.

This impressive reflecting pool stretches out 690 feet in length, 100 feet in width, and has a depth of just 26 inches. It is made from curved, polished Minnesota red granite and is typically filled for up to seven months per year (usually from April to November). Then it’s drained for the winter.

Museum of Fine Arts

With more than 8,000 paintings and over 450,000 works of art, the Museum of Fine Arts in Boston is the 20th-largest art museum in the world. If you’re a museum enthusiast, you can easily dedicate an entire day to exploring its large and diverse exhibits.

Back Bay Fens

I stumbled upon this park on my way to the Isabella Stewart Gardner Museum. As I was walking along Boylston Street from the Boston Public Library, I reached a small bridge named Boylston Bridge. The view of the park from up there was lovely and I decided to take a stroll on my way to my next destination.

I was surprised by the size and different vibe of Back Bay Fens. The park is called “The Fens” by the locals and it is home to a few memorials and statues, gardens, playgrounds, and picnic areas.

Harvard 

Harvard is a town situated about 25 miles northwest of Boston. It is known for Harvard University, a prestigious private institution that is a member of the Ivy League. Founded in 1636, Harvard University is the oldest higher education institution in the United States. With an average cost of $13,000 after financial aid and an acceptance rate of 4%, Harvard University is synonymous with prestige and ranks as a leading university, not only in the United States but also globally.

To reach Harvard from the Boston Common area, you can take a train. It will get you there in approximately 30 minutes (via the Red Line, with a fare of $2.40). The train conveniently drops you off right next to Harvard Yard, where you’ll find Harvard University, Harvard College, and many other historic buildings. While strolling through the campus, you’ll come across Robinson Hall, Emerson Hall, Harvard Library, and more. Make sure you visit the statue of John Harvard in front of University Hall. Don’t forget to rub his shoe, as legend has it that it brings good luck!

After you check out the most iconic place in the town of Harvard, take a walk through Downtown and Harvard Square. You can spend some time at Winthrop Park and grab a souvenir from one of the stores with authentic Harvard University merchandise. Go have lunch at The Red House right behind Winthrop Park. I was in Boston in July and I really liked their cold avocado salmon soup. It was perfect for the hot day that I was visiting!

Cow Parade

As you explore Boston, you will definitely notice an unusual sight- cow statues displayed at random places. When I saw the first one, I thought “Cool!” but as I continued to see more, each painted in unique ways, I got interested and decided to look it up.

Turned out that the cow statues were part of an initiative called “Cow Parade.” This initiative aims to support cancer research for the Cancer Institute. There are 75 life-size cow sculptures placed across the city, each painted by local artists and showcased at businesses that purchased them to make a donation.

Since Boston is very walkable it is absolutely possible to cover the first-time visitor musts for three or four days. I highly recommend using my strategy “Divide and conquer”. For those of you who are not familiar, “Divide and conquer” is a planning approach I’ve been using for a while. It significantly optimizes my time when exploring a new destination. It involves categorizing landmarks and activities by neighborhood and allocating specific neighborhoods to different days of the trip. This way, I can make the most of my visit and ensure I don’t miss out on anything worth experiencing.

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Here’s how I covered all the places above plus more in 4 days:

What sets Boston apart from many other cities is how walkable it is and the close proximity of many local landmarks. Boston is a beautiful blend of a big city with its skyscrapers and the charm of a small town with its distinctive architecture. If you plan to visit, I’d recommend dedicating a minimum of 3 days. This will allow you to fully immerse yourself in the best spots this city has to offer.

Have you ever been to Boston? What’s your favorite place there? Let me know in the comments below!