This Boston itinerary is a perfect fit if you’re planning a weekend in the city.

I’ve spent multiple weekends exploring downtown Boston, so I’m a pro at fitting a lot of really fun things into a short visit.

Recently I spent about a day and a half in the city (36 hours total!), and I was impressed with just how much you can see in that time (thank you public transportation).

Keep reading for the best things to do, see, and eat across the city of Boston.

Perfect Boston Itinerary: 2 Days in Boston

So you’ve got two days to spend in Boston eh? No problem! Here are some of the city’s most incredible attractions.

You can explore a lot of Boston on foot. If you’re visiting museums or the Prudential Center, book your tickets ahead of time to avoid lines.

Let’s dive in.

What to See in Boston

Here are the top attractions across Boston for your weekend trip.

Freedom Trail

This is my top recommendation in Boston. If you visit Boston in warmer months, explore part or all of the Freedom Trail.

This storied 2.5 mile route through Boston is full of iconic landmarks like the Paul Revere House, Trinity Church, Old North Church, Bunker Hill Monument, Granary Burying Ground, Old South Meeting House, and American Revolution historic landmarks.

Get all the information you need on the Freedom Trail’s official website. The trail starts either in Beacon Hill or Charlestown across the river.

Prudential Center

Wow, I cannot recommend a visit to the Prudential Center enough.

This 52 story building whisks you above the city for 360 degree views. Go during the day and book a reservation or grab drinks at one of the restaurants or bars.

We visited on a cloudy night, and it was still one of our favorite activities. The interior public viewing levels have bars and live music in the evenings, making for a romantic date night.

Boston Public Library

The Boston Public Library is famous for being America’s oldest large public library.

The current building, built in 1895 in the Renaissance Revival style, is genuinely gorgeous inside and out.

The grand entrance hall and staircase, regal statues and artwork across Bate’s Hall and Sargent Gallery, and profound collection of rare books are well worth a visit.

Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum houses an impressive private collection of artwork from a 19th century female art collector.

Isabella Stewart Gardner traveled the world collecting art, and built this stunning 3-story building to house her collection for the public to enjoy.

Enjoy towering rooms filled with art from Rembrandt to Michelangelo, along with the museum’s Venetian Gothic Revival architectural style. This is a perfect rainy day or cold weather activity in Boston.

Fenway Park

Fenway Park is a top choice whether you’re attending a Red Sox Game or snapping a picture in front of this iconic building.

After growing up with films and stories of Fenway Park, it feels surreal to visit in person!

Harvard Square

A walk across Harvard University makes for a perfect afternoon activity.

You’ll have to hop over to Cambridge for it, but it’s well worth the short walk or drive to the square’s many restaurants, shops, and museums.

While you’re in Harvard Square, stop over to Harvard Yard and the widely photographed John Harvard Statue.

Boston Public Market

This is an indoor, year round local market that features 30 vendors. The venue is a great spot for unique gift shopping.

I love the mission of the market to support New England farmers, food producers, and entrepreneurs through its two locations (Downtown at 100 Hanover Street and Terminal C at the Boston Logan Airport).

At the downtown location, pick up fresh groceries, prepared meals from bagels to New England seafood, or even local jewelry and spices.

Boston Common

The sprawling Boston Common is America’s oldest public park.

And as one of our friends described it, its also THE go-to spot for Bostoners to get out into the sun during the summer months.

The park was a space for Colonial militia to prepare for upcoming battles in the Revolutionary War, so you can only imagine the deep history here.

A few ideas for your visit – paddle a giant swan boat into the lake, explore the grounds including the George Washington statue, or picnic on the open lawns.

Boston Museums

Boston is a great place to visit highly rated museums.

Book tickets to the Museum of Fine Arts, Science Museum, John F. Kennedy Presidential Library and Museum, USS Constitution Museum, Isabella Swan Museum (listed above), or Museum of African American History – all great choices for an afternoon.

Quincy Market

The historic Quincy Market originally opened in the mid 1820’s selling meats, cheeses, and seafood.

Fun fact – it’s namesake Mayor Quincy was able to found the market without raising city taxes.

In the 1970’s the market was reimagined into its present form – a bustling building with cozy food stalls and shops.

Take a lap around the market for a build-your-own sort of food tour of incredible local restaurants.

Where to Walk in Boston

Unless the weather calls for it, you don’t need a car when you visit Boston.

Instead, go it on foot or take Massachusetts Bay Transportation Authority (MBTA) – AKA “the T” – around to different neighborhoods.

In poor weather, consider public transportation or ride share to avoid parking hassles.

Beacon Hill

Beacon Hill is a quintessential Boston neighborhood and a jumping off point for the Freedom Trail.

I’d put Beacon Hill at the top of your list for it’s historic homes and the fantastic shopping and dining along Beacon Street.

The neighborhood is known for its olden day gas lamps and cobblestone streets that will whisk you back in time.

Speaking of, be sure to visit Acorn Street, one of the most photographed streets in the US.

North End

North End is another historic gem of a neighborhood full of brick rowhomes, old churches, and “Little Italy”.

This is your stop for exceptional Italian cuisine and key landmarks on the Freedom Trail.

Consider taking a local food tour, visiting Scarlett O’Hara’s house (a shockingly realistic mural), or stopping at the Skinny House – one of the thinnest buildings in the world.

China Town

Step through the towering China Town gates into this historic Boston neighborhood.

While there, enjoy authentic Chinese and Taiwanese cuisine, shop for delicious baked goods, visit a tea house, or book a China Town tour.

Where to Take a Tour in Boston

No matter where you go in Boston you’ll find streets and buildings steeped in history.

Boston Harbor

There’s no better way to dive into Revolutionary War history than the Boston Tea Party Museum at Boston Harbor.

Get fully immersed into the events leading up to the Revolutionary War with live reenactments and replica tea ships.

This is one of the biggest events in early American history, so if you book one tour for your Boston itinerary this can be a great choice.

Neighborhood Food Tours

Boston is famous for its lobster rolls, clam chowder, fried clams, seafood, and Boston cream pie. P.S. you absolutely have to try lobster rolls while in town (I don’t want to exaggerate, but its life changing).

Book a food tour or tour guide in for your Boston itinerary. I recommend Beacon Hill, North End, China Town, Davis Square, or Jamaica Plane.

A guided tour is perfect for foodies who want to hit up a bunch of the best in Boston quickly.

Where to Eat in Boston

Boston is a perfect place to get authentic Italian, fresh seafood, and Boston favorites like lobster rolls and clams.

Eatily

Okay I was in love with Eatily the moment I found it.

This is like a world of Italian dishes across separate food stalls under one roof.

Order handmade pasta, pastries, and coffee, then grab your favorite Italian ingredients to take home.

The Salty Pig

The Salty Pig is a no-fuss Italian restaurant with fantastic pastas and appetizers (we didn’t try the pizza but it is highly rated).

Order house-made pasta, gluten free pasta, hand tossed pizza, and drinks.

And if I may, order the beat appetizer.

Lukes Lobster Back Bay

Don’t leave Boston without getting a lobster roll from Luke’s Lobster.

This was the recommended spot from a Boston local, and it did not disappoint. We still tell stories about this lobster roll to friends.

Their clam chowder is also fantastic, and perfect to warm up during cooler weather.

Where to Stay in Boston

Boston’s historic neighborhoods feature five star hotels and popular Airbnbs for a cozy stay.

Even if your Boston itinerary is jammed packed with activities, its lovely returning to a beautiful hotel looking over the city.

Back Bay

If you want to stay in a historic Boston neighborhood Back Bay is a top choice.

The tree-lined streets and popular restaurants are accessible from your hotel and the T station (Back Bay Station).

We stayed at the Boston Marriott Copley Place and I’d absolutely stay there again.

Back Bay is well located next to Beacon Hill so you can get to historic sites, shopping, and dining in a few minutes.

Boston FAQs for Your Boston Itinerary

Where do I fly into Boston?

You’ll fly into Boston Logan International Airport to arrive in Boston.

How do I get from the Boston Airport into Boston?

Boston is one of the rare US cities with good public transportation.

You have several good options to go from the airport into the city.

The Logan Express bus line is quick and dependable. We used the bus on our last weekend trip to Boston and it was seamless from the airport to Copley Square.

The MBTA Blue Line subway is another good option for public transport.

You can also get a rideshare or rental car at the airport.

What is the best time to visit Boston?

This Boston itinerary is really designed for any time of the year.

I’ve been advised that May to June and September to October have excellent weather and are less crowded.

Go late spring to early fall for warm walking weather. Visit in the fall for changing leaves, or December for Christmas vibes (the Christmas markets and shopping malls are so cute!).

I’ve honestly had a great time visiting in December the last 2 years. Yes it’s chilly, but Boston is beautiful in the snow.

Pro Travel Tip: Packing for weekend travel is a whole art. Here are 3 of my best tips for packing jeans with limited space in your bag.

What is the Weather like in Boston?

Boston gets all four seasons.

• Winter: Cold with snow.
• Spring: Mild weather with potential cold periods.
• Summer: Generally hot and humid, with July the peak for heat.
• Fall: Cooler weather and beautiful changing colors on trees.

Boston Itinerary: Final Thoughts

As you’re probably finding out, Boston is one of the most historic cities in the United States.

And even if it’s not your first time visiting the city, there is so much to do and see in a 2 day trip.