2 Days in Boston: A Classic Weekend Itinerary (+Map)

Planning to see Boston in 2 days? Get ready to be spoilt for choice!

Boston, located on the East Coast in Massachusetts, United States of America, is a historical city with a European charm.

As one of New England’s most populated cities, Boston enjoys four distinct seasons, making it a great getaway, especially during spring, summer, and fall. 

Whether it is parks, historical neighborhoods, museums, water-based activities, seafood, or culture – there’s something for every traveler visiting the city.

Boston is undoubtedly one of the best places to visit in New England!

Additionally, Beantown, as the city is fondly nicknamed, is also a great starting point for several New England weekend getaways.  

Are 2 days in Boston enough? Probably not. It is impossible to do justice to this culture rich city in such a short period!

Having said that, here are some ideas on how you can plan the best 48 hours in Boston.

How to Spend 2 Days in Boston – Itinerary
Getting Around Boston
Boston 2 Day Itinerary Map
Where to Stay in Boston

2 days in Boston itinerary

Day 1: Gardens, charming neighborhoods, history, seafood and cannolis!

Boston Public Garden

Nearest subway stop: Arlington, Green Line

Boston Public Garden is America’s first botanical garden.

Situated in the heart of the city, this large Victorian-style park is well worth a visit in any season.

In the spring, daffodils and cherry blossom trees attract locals and visitors alike. Summer and fall are other popular times of the year to visit.

A photo of Boston Public Garden
In Boston for the weekend? Don’t miss Boston Public Garden, which is beautiful all year round.

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The park is the perfect place to enjoy a picnic amidst flora and fauna, by a small lake.

Don’t forget to grab a coffee and croissant from nearby cafes Tatte Bakery or Thinking Cup.

Season permitting, you can also enjoy a 15-minute swan boat ride ($4.50). No reservations are needed for booking the swan boat ride. 

No matter when you’re here, walk around or simply relax under the shade of one of the giant trees.

Before you leave, snap a photo with the duckling statues located close to the park entrance at the intersection of Charles Street and Beacon Street.

The statues are a tribute to Robert McCloskey’s classic children’s picture book, Make Way for Ducklings

Beacon Hill

Nearest subway stop: Arlington, Green Line

With its brick sidewalks, tiny sloped lanes, and federal style row houses, Beacon Hill is one of Boston’s most charming neighborhoods. It is only a short walk away from Boston Public Garden.

While Beacon Hill is a residential neighborhood, there is no dearth of places to eat, cafes, boutiques, or shops.

Things to do in Beacon Hill

Visit America’s most beautiful street

Beacon Hill is home to Acorn Street, a short, sloping narrow street, that is known as one of America’s most beautiful streets, and rightfully so.

The cobblestone street and historic homes lend a colonial vibe to the street, making it irresistible for photographers.

A photo of a cobblestoned Acorn Street in Beacon Hill, Boston
Acorn Street is truly beautiful in every season

See the former homes of noteworthy authors

If you’re a literary lover, you’re in luck. Former homes of authors including Louisa May Alcott (20 Pinckney Street), Henry David Thoreau (4 Pinckney Street), and Robert Frost (88 Mount Vernon Street) are on Beacon Hill!

Have brunch at Boston’s favorite diner

The Paramount is a classic eatery serving up pancakes, waffles, and traditional American breakfast. Make sure to get there early, as there’s always a queue outside.

Dig into divine pastries at a modern bakery

Visit Tatte Bakery & Cafe, for coffee, croissants, a middle eastern-inspired brunch, and incredible desserts.

Admire stunning floral arrangements

Rouvalis Flowers, located at the intersection of Pinckney and West Cedar street is worth a stop for its floral displays and garden ornaments.

Learn about the history of African Americans in New England

The Museum of African American History, located on Joy St., is the region’s largest museum preserving the contributions of African-Americans in the area. Tickets are priced at $10.

Shop for creative stationary

Go to Black Ink on Charles St. for hip stationery, various knickknacks and vintage posters.

Grab a drink at an iconic bar

Cheers, a bar that inspired the popular NBC TV show of the same name, is located on Beacon Street. 

Visit a premium chocolatier

Beacon Hill Chocolates is another must-visit store for seasonal chocolates.

Tour the gardens of Beacon Hill

In May, the Beacon Hill Garden Club holds an annual ‘Hidden Gardens of Beacon Hill‘ tour that takes visitors through urban gardens and secret pathways in the neighborhood. 

A garden in Beacon Hill, Boston
Beacon Hill is among Boston’s most beautiful neighborhoods

Go clicking

Fall is when photographers throng Beacon Hill. The neighborhood is situated on a hill, making it a beautiful setting for fall photographs in October or November.

Halloween is also a popular time to visit to see decorations and celebrations underway.

See holiday decor

In the winters, local Beacon Hill homeowners showcase their creativity with spectacular holiday decor, making a visit highly worthwhile.

Regardless of what you choose to do in Beacon Hill, it is a neighborhood that surely deserves to be on every 2 day Boston itinerary.

Freedom Trail

Nearest subway stop: Park Street, Green Line

Walking the 2.5-mile (or 4 km) long Freedom Trail is one of the best things to do around Boston.

Starting at the Boston Common (another expansive garden that’s a must-visit) next to Boston Public Garden, this trail will take you through historical landmarks that play a significant role in the history of United States.

Fall colors at Boston Common, Boston
Start your Freedom Trail walk at the expansive Boston Common

What’s interesting about the trail is that the sites are sprinkled across the city’s downtown, so you will pass through stores, cafes, neighborhoods, and shops during your walk.

Be sure to take a moment to admire the golden dome atop Massachusetts State House. 

The following sites are included in the Freedom Trail walk:

  1. Boston Common
  2. Massachusetts State House
  3. Park Street Church
  4. Granary Burying Ground
  5. King’s Chapel and King’s Chapel Burying Ground
  6. Boston Latin School Site/Statue of Benjamin Franklin
  7. Old Corner Bookstore
  8. Old South Meeting House
  9. Old State House
  10. Boston Massacre Site
  11. Faneuil Hall
  12. Paul Revere House
  13. Old North Church
  14. Copp’s Hill Burying Ground
  15. USS Constitution
  16. Bunker Hill Monument

If you’re short on time, you could pick and choose to visit a few points on the trail, but it is ideal to take a guided Freedom Trail tour for an enriching and entertaining experience. 

Finding the right tour can be tricky. This guided tour of the Freedom trail provides a holistic perspective on the American revolution through enthusiastic storytelling.

A freedom trail marker
Walking the Freedom Trail is a great way to learn about American history

Quincy Market and Faneuil Hall Marketplace

Nearest subway stop: Haymarket or Government Center, Green Line

A historical market and public hall that has been in existence since the 1800s, Faneuil Hall Marketplace and Quincy Market have attractions for every type of traveler.

From street performances to lobster rolls, clam chowder, and Boston cream pies, branded stores, to vintage items and souvenir shops, and even a giant Christmas tree with a light and sound experience – this area is buzzing all year round. 

Vendors outside Quincy Market, Boston
There’s lots to see and do in Faneuil Hall & Quincy Market

Quincy Market is a historical building with mostly food vendors surrounded by the cobblestoned Faneuil Hall Marketplace outdoor space where the performances are held and other vendors are present. 

This is an ideal place to grab a quick meal surrounded by a vibrant atmosphere, especially after you have walked around the city.

Things to do in Quincy Market and Faneuil Hall Marketplace

Taste Clam Chowder

New Englanders take real pride in their chowda! Taste traditional clam chowder at Boston Chowda Co. inside Quincy Market.

Try a lobster roll

Try a lobster roll at Wicked Lobsta or Boston & Maine Fish Company. For a more upscale dining experience, head to Legal Seafoods on Downtown Crossing or Long Wharf.

Discover the delicious Boston Cream Pie

Enjoying a Boston cream pie in Boston is what every traveler to the city must do. It is a 2-layer cake with vanilla, custard/cream filling, topped with chocolate sauce.

Try the Boston Cream Pie at North End Bakery inside Quincy Market.

Street performances

Watch street performers, jugglers, musicians, and magicians at the Faneuil Hall Marketplace.

Take an Old Town Trolley Tour

Book tickets for an Old Town Trolley Tour right at the marketplace. Tours start at $45.

Browse a nearby market

  • Walk to Haymarket, Boston’s historic farmer’s market, and sample fresh produce and cheese from local vendors.
  • Visit Boston Public Market next door, an indoor marketplace where you can find modern food and drink vendors and, locally handcrafted goods.

Boston Tea Party & Museum

Nearest subway stop: South Station, Red Line

Relive history by learning about the events that led to the start of the American Revolution at the Boston Tea Party & Museum.

A view of the Boston Tea Party Ships & Museum on the Boston waterfront
Visit Boston Tea Party & Museum for an interactive historical experience

Only about a mile from North End, the Boston Tea Party & Museum provides visitors with a chance to reenact history through participation in their interactive exhibits, along with costumed interpreters.

Here, you can tour an 18th-century replica sailing vessel, see the Robinson Tea Chest, which is the only surviving tea chest from the Boston Tea Party.

Get your admission tickets for a live guided tour inside the Boston Tea Party Ships & Museum to see the authentically restored tea ships.

North End

Nearest subway stop: Haymarket, Green Line

Boston’s Italian neighborhood is the perfect blend of the past and present and thereby deserves to be on every itinerary to the city.

The neighborhood has been in existence since the 1630s and is one of the city’s oldest residential neighborhoods, retaining its charm through the centuries. 

North End is also the ideal place to end an evening with a fine meal.

A photo of a street crossing at Boston's historical North End
North End, Boston’s Little Italy is a must include on your Boston weekend itinerary

Though you will visit the area to see Old North Church if you’re on the Freedom Trail, it is best to return to the neighborhood separately.

Things to do in North End

See the Skinny House

Located on 44, Hull Street, this house is said to be the skinniest four-story house in all of Boston.

Find the ultimate plate of pasta

The pasta at Trattoria Il-Panino is one of the best in the area! There are way too many dining options in North End, but this one would surely be a highlight of your Boston trip.

Savor a cannoli..or two

Visit Mike’s Pastry or Modern Pastry for their famous cannolis…or visit both and decide for yourself which of these two pastry shops makes better cannolis!

Try Sicilian pizzas, arancini, and more

Grab a Sicilian-style pizza from Galleria Umberto, a hole-in-the-wall restaurant. Get there during the day time though, since they typically have a queue and sell out by the late afternoon. Cash only!

Shop Italia

Shop for authentic Italian goodies from Salumeria Italiana.

Buy a beautifully baked loaf of bread

Pick up some artisan bread from Bricco Panetteria.

Italian coffee, anyone?

Sip some fine coffee at Polcari Coffee.

If you’re a gourmand who also appreciates history, look no further. Boston is just the place to satisfy your belly and your curiosity.

Book tickets for this intimate food and history walking tour that offers the fantastic experience of tasting delicious food in North End and learning about the rich history of the Freedom Trail.

Day 2: Universities, baseball, hip neighborhoods, and a sunset cruise

Harvard University & Harvard Square

Nearest subway stop: Harvard Square stop, Red line

Start your day across Boston’s Charles River in the town of Cambridge, one of the city’s most popular neighborhoods and home to the iconic Harvard University.

Begin at Harvard Square, the center of all the action. 

Many of the Harvard University school buildings are spread across Cambridge and parts of Boston, but the main University campus is located in Harvard Square. 

A view of Harvard University's library on their campus
A visit to the Harvard University campus is among the best things to do in Harvard Square

For a quick self-paced tour, head inside Harvard Yard or “Yahd” to see the statue of the college’s first benefactor, John Harvard. Walk around to see the red brick buildings in the same enclosure. 

Got some more time on your hand? Get a glimpse of life on campus with an insightful 70-minute tour of Harvard University with a current student.

Harvard Square has plenty of cafes, bookstores, quirky shops, and the area has a unique vibe that is quite different from downtown Boston. The best way to see Harvard Square is by wandering around.

Things to do in Harvard Square

Sip the best hot chocolate

If you’re a chocolate lover, march over to L.A. Burdick for their delicious, thick hot chocolate and choicest pastries.

Find your kind of food & drinks

Browse books

See a band perform

Catch a live band performance at The Sinclair. Reservations recommended, especially if you are planning a weekend Boston trip.

Visit a Harvard Museum

  • Admire art from several parts of the world at Harvard Art Museums. Currently, advanced reservations are required for entry. Tickets are priced at $20 for adults. The museum is free for children. They also offers a free Sunday program.
  • The Harvard Museum of Natural History is another exciting place for those interested in admiring prehistoric artifacts. Currently, the museum is closed to visitors. Normally, tickets for entry are priced at $15.
Side Visit: Massachusetts Institute of Technology

While you’re in the area, and if time permits, make your way to the Massachusetts Institute of Technology (MIT), another prestigious campus in Cambridge, not too far away from Harvard Square.

Marvel at the complex architecture of Stata Center, which features tilted towers and whimsical shapes, or walk over to see the Alchemist statue, made of stainless steel symbols and numbers.

Another noteworthy spot on the campus is the much-photographed MIT Great Dome, across the Charles River.

Fenway Park

Nearest subway stop: Kenmore Square, Green Line

Fenway Park, the mecca for baseball lovers is located near Kenmore Square in Boston. This beloved 100+ year ballpark is home to the Boston Red Sox and has a seating capacity of 34,000.

The best way to experience the vibrant atmosphere of Fenway Park is through a live baseball game. Plan a visit between April-October to catch a baseball game in person.

An ariel view of Fenway Park
A view of Fenway Park

Tickets to a game need to be reserved in advance. Otherwise, take an hour long guided tour that allows visitors to explore the historic grounds and learn about players, teams, and moments of sporting history.

Newbury Street

Nearest subway stop: Hynes Convention Center or Copley, Green Line

Located in the posh neighborhood of Back Bay, Newbury Street is a mile-long street with brownstone buildings, known for its shops, eateries, and modern, upscale vibe.

Being relatively close to downtown, Boston Public Garden, Copley Square, high-end hotels, and universities, Newbury Street is a fun hangout for locals and visitors alike. 

Historical brownstone buildings in Newbury Street, with shops and cafes
Planning on shopping in Boston? Head to Newbury Street for boutiques, brands and more!
Things to do in Newbury Street

Shop till you drop

Stroll through to see the trendy boutiques, high-end branded stores. Newbury Street is home to a range of brands from Zara, H&M to Marc Jacobs and Chanel.

Try a rose shaped gelato or a Japanese style dessert

Grab a rose-shaped gelato cone from Amorino

Or, try a Japanese-style Signature Mille Crepes from Lady M Boutique

Find a meal of your choice

  • Have lunch with a side of a bestseller book at Trident Bookseller’s Cafe, a local favorite
  • Settle down for cocktails and a meal at one of the nice restaurants in the area. Cuisine options range from Italian, American, Mexican, Indian, Japanese, Seafood, Southern comfort food and more! 
  • You could also dine and shop for authentic Italian pasta, wine, cheese, and snacks at Eataly, inside nearby Prudential Mall. Eataly is an Italian market, gelato shop, with restaurants. 

Head to nearby Copley Square for more attractions

  • Visit Boston Public Library, across from Copley Square, which has marvelous interior architecture, and also offers high tea at its Courtyard Tea Room.
  • Walk around to admire the nearby Trinity Church.
  • If you visit during a summer afternoon, you may see a farmer’s market at Copley Square too.

Boston Harbor Sunset Cruise

Nearest subway stop: Haymarket or Government Center, Green Line for Long Wharf,
South Station, Red Line for Rowe’s Wharf (both are about half mile walks from each station)

There’s no better way to end your 2 day trip to Boston than on the city’s waterfront.

Watch the sun go down on an exclusive night under the stars, surrounded by the water, with the Bostonian skyline glittering at a distance.

A photo of the Boston skyline. Being on the waterfront is the best way to wrap up 2 days in Boston.
There’s no better way to admire the Bostonian skyline than from the waterfront!

Sunset cruise tours are offered from Long Wharf, Central Wharf and Rowes Wharf. Depending on the direction of the wind, the ship Captain takes a decision on the route.

You might also get a chance to see some of the small islands off the coast of the city from the observation deck. 

Here’s a Boston Harbor Sunset Cruise that takes visitors in a classic schooner or a tall ship.

It is truly a fabulous way to wrap up 2 days in Boston. 

Getting Around Boston

Love to walk? In that case, Boston is the perfect getaway for you! The city is also well connected by public transport. Cabs and ride-sharing services are available too.

If you’re flying into the city, here are some ways to reach Boston downtown from the airport, and then get around in the city:

Free airport shuttle

Take the Massport free shuttle that provides bus service between airline terminals, the rental car center, and Airport Station on the MBTA Blue Line.

Look out for these shuttle buses at the lower level of each terminal. The MBTA blue line is the city’s subway system. It can easily get you to the Government Center station in downtown.

Ride service or cab

Book an Uber / Lyft ride. Each terminal has a specific parking lot designated for ride-sharing cars.

Follow directions at the airport and make your way to the Uber/Lyft parking lot. This option is ideal if you’re planning a weekend trip to Boston.

Alternatively, you can also book a prepaid cab. Cabs have a designated pick-up area outside each terminal too.

Both cabs and ride sharing services are easy options for shuttling around within the city as well.

The T sign indicating Boston's subway system
Look out for the T sign if you’re taking the MBTA to zip around Boston


The MBTA or the subway transport system, known as the T, connects most neighborhoods in downtown Boston and Cambridge.

You would need to purchase a Charlie Card if you plan to use the subway frequently.

Charlie Cards are available at the select stations like North Station or South Station.

You can also buy a Charlie ticket for single or round trip rides or pay cash for a ticket when you board a subway train. These are available at the vending machine in each station. 

The red line subway stops at Harvard Square in Cambridge. The green line subways (B, C, D trains) connect major sections of downtown Boston.

Both red and green lines intersect at the Park Street station next to Boston Common.

Rent a car

Though not ideal for two days in Boston, you could also rent a car from the airport. You can take a free shuttle from each terminal to pick up the rental car from the airport. 

Boston 2 day itinerary map

Plan ahead for jetting around if you choose to spend two days or a weekend in Boston. Here is a map with all points of interest mentioned in this post, along with subway stops to help you prepare.

Where to stay in Boston

If you’re wondering where to stay in Boston for a weekend or two days, you have plenty of choices.

Getting around would be easier if you chose to be close to most landmarks. The following stay options are ideal for a quick trip to Boston.


The Newbury Boston: Located in the heart of Boston, The Newbury offers timeless rooms with original artwork and an exceptional rooftop restaurant and bar.

Most rooms come with views of the Boston Public Garden, and the posh Newbury Street is a few steps away. Opt for a city view king room or a suite with a wood-burning fireplace.


Fairmont Copley Plaza: Among the best Boston hotels in the heart of Copley Square, close to Back Bay, the Fairmont hotel will delight you with its majestic architecture.

The hotel is close to Boston Public Library, Newbury Street, and Trinity Church.

Guests have particularly appreciated the size of the rooms, the bar and breakfast area, and the customer service. The hotel offers king, queen, studio, and suite rooms.


HI Boston Hostel: A five-minute walk from Boston Common, HI Boston offers 4 and 6-bed dorms and private rooms with private bathrooms.

Book well in advance as rooms sell out quickly.

Guests, in particular, love the fact that the property is clean, organized, is within a reasonable price point, and at a great location.

The hostel offers a shared kitchen, pool table, TV, and a coffee vending machine too. 

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