2 Days in Boston: a Step-by-Step Itinerary

“I guess no true Bostonian would trust a place that was sunny and pleasant all the time. But a gritty, perpetually cold and gloomy neighborhood? Throw in a couple of Dunkin’ Donuts locations, and I’m right at home.”

Rick Riordan

Before going into details on how to spend 2 days in Boston, let me tell you a little about my relationship with this city. I lived near Boston for over a year. I wish I could substitute “in” for “near”, because it would be wicked awesome to be a Bostonian for a little while. To look smart, act snobby, and say “Hahvahd Yahd”. Although, that last one might be particularly hard since I am Russian and like to roll my r’s.

I lived 40 minutes away in New Hampshire. I would come to Boston on weekends and brave the cold to celebrate my first ever Thanksgiving Day, to have a bite of original Boston Cream Pie, or sip a drink at the bar where scenes from Good Will Hunting were filmed. In those memories, Boston is always cold, windy, and gloomy.

After a year in Nashua, NH, my husband and I moved to Austin, Texas. One summer his job took us back to Boston for a full month. I didn’t work at the time, so I made it my job to explore Boston’s cobblestone streets and eat lobsters for breakfast, lunch, and dinner. Mom says I am a bourgeois, but lobsters for Boston are what grits are for the South, right?

For the first time, I felt warm in Boston. Warm to be outside without layers of clothes and the fear of getting frostbites, but also simply welcome. This 48 hours in Boston guide was born out of five weeks of explorations. It involves ridiculous amounts of walking simply because I finally could walk in the sun-lit streets, and so I did. Here’s how to see the best of Boston in 2 days!

Disclosure: this post contains some affiliate links which means if you buy something by clicking the link I will earn a small commission at absolutely no extra cost to you.

How to Spend 2 Days in Boston: Day 1

Neighborhoods: Waterfront, The North End (Little Italy), Downtown, Chinatown, Beacon Hill, Back Bay

Distance: 5.4 miles (8.7 km)

9.00 – Breakfast from James Beard Award Winning Chef at flour

One of my go-to places in Boston, flour bakery boasts a great selection of scrumptious pastries which makes it a perfect choice for breakfast. Who wouldn’t like a warm banana bread, a ham and cheese croissant, or brown butter cinnamon rolls to start the day? Besides pastries, they offer a variety of sandwiches and grain bowls.

flour offers consistently delicious, fresh, and affordable (very important in Boston) meals. The owner and pastry chef of flour, Joanne Chang, is a source of inspiration to me. A graduate of Harvard College with a degree in Applied Mathematics and Economics, Chang turned into a pastry chef, opened eight locations of flour in Boston and Cambridge, wrote several cook books, and received James Beard Foundation Award for Outstanding Baker. Pretty awe-inspiring, right?

Tip: Out of many flour locations the one on Farnsworth Street is the most comfortable for this guide’s purposes.

flour Bakery – 12 Farnsworth St.

10.00 – Refreshing Walk at the Waterfront

From flour bakery start walking towards the North End (Little Italy). Cross the Seaport Boulevard Bridge and stroll along Harborwalk which is a public walkway that stretches 43 miles along Boston’s shoreline. Don’t worry, I am not going to make you walk the length of 1.5 marathons. Walking from flour bakery to the North End will take no more than half an hour. Make sure to stop at one of the wharves to get beautiful views of the harbor.

10.30 – the North End, Little Italy of Boston

The North End is Boston’s first neighborhood also referred to as Little Italy. Although incredibly small (only 0.36 square miles), it is one of the liveliest neighborhoods in the city with its many Italian restaurants, coffee shops, delis, and bakeries.

The North End is also a great way to learn about the history of American Revolution: the Paul Revere house, Copp’s Hill Burying Ground (Boston’s second-oldest cemetery), and Old North Church are all located in Little Italy.

11.30 – the Rivalry of Cannoli

I can’t emphasize this enough: your 2 days in Boston itinerary must include the legendary cannoli from Mike’s Pastry and Modern Pastry. Both shops are located in the North End, almost exactly across the road from each other. There are people who say Mike’s cannoli are the best cannoli you can find outside of Italy. There are others who claim Modern Pastry’s cannoli are the most authentic and delicious. You have to try both and decide whether you are on team Mike’s or team Modern. You can also decide to be on team Cannoli and just eat a whole bunch from both shops.

Tip: Bring some cash, neither of the shops accepts credit cards. The lines are long, but they move quickly.

Mike’s Pastry – 300 Hanover St.

Modern Pastry – 257 Hanover St.

12.00 – Boston Market District

Boston Public Market is located a few minutes away from the North End and is open seven days a week. This indoor year-round marketplace offers fresh local foods produced in Massachusetts and New England.

On Fridays and Saturdays from dusk to dawn, you can also visit historic Haymarket located nearby, on Blackstone, Hanover, and North Streets. Merchants gathered at the location of the current Haymarket from around 1830-s. The produce is usually several times cheaper than in supermarkets, especially if you come by the end of the day.

Boston Public Market – 100 Hanover St.

12.30 – Original Boston Cream Pie at Omni Parker House

From Boston Public Market walk to Omni Parker House (10 min), a historic hotel in downtown Boston. The hotel, formerly known as Boston’s Parker House, has been around for the past 160 years. The famous Boston cream pie was invented here, at Parker restaurant, located inside Omni Parker House. Although this is not my favorite version of Boston cream pie, it is genuinely good. Besides, I think it must be obligatory to try the original Boston cream pie when you spend 48 hours in Boston. By the way, the hotel is worth stopping by even if you are not in the mood for sweets. The interior design is stunning.

To learn how to get the pie without having a dinner at Parker Restaurant, check this post about the history of the legendary dessert.

If you want to know who makes my favorite Boston cream pie check out this guide to the best desserts in the city.

Omni Parker House – 60 School St.

13.00 – Brattle Book Shop, a Book Lover’s Paradise

One simply cannot spend 2 days in Boston and not visit Brattle Book Shop, one of my favorite places in the city. Housed in a three-story building, Brattle is one of the largest used book shops in the country with 250 000 books in stock. Two floors feature general used books, while the third floor is dedicated to antiquarian books and first editions. My favorite space in Brattle, though, is the open lot outside with books for sale. Located in between two red brick walls, the lot houses carts with books that cost as low as one dollar.

Brattle Book Shop – 9 West St.

14.00 – Dim Sum in Chinatown

Boston’s Chinatown is the third largest in the United States, right after New York and San Francisco. It is also the only surviving ethnic Chinese area in New England since the demise of Chinatowns in Maine and Rhode Island in the 1950-s.

The best way to explore Chinatown is through its many amazing foods. Wander around the neighborhood, pop into some of the Asian grocery shops, and eat dim sum in one of the many restaurants in the area. Winsor Dim Sum Café is an unassuming little restaurant serving great dim sum at reasonable prices. A big satisfying lunch for two will set you back $20-25.

Tip: they don’t accept credit cards for orders less than $10.

Winsor Dim Sum Café – 10 Tyler St.

Alternative: If you are not in the mood for Asian food, check out Mast’ for one of the best pizzas in the city.

Mast’ – 45 Province St.

15.00 – Book-Inspired Art and Movie Locations at Boston Public Garden

After lunch, head to Boston Public Garden, a beautiful park adjacent to Boston Common. Whenever I am in the area, I never skip a chance to walk around the garden, if only for a few minutes.

One of the most classic tourist attractions is swan boat rides which started back in 1877. Another fun thing to do, especially if you have kids, is to find Make Way for Ducklings statue. The bronze ducklings are dressed in ridiculously cute outfits for Christmas, Saint Patrick’s Day, Super Bowl, and other occasions.

And if you are a fan of visiting movie locations, find the Good Will Hunting bench, on which Robin Williams and Matt Damon had a talk in the Oscar-winning movie. Here’s the location of the bench on Google Maps.

Tip: If you are a fan of the TV-show Cheers, the famous Cheers bar is located just outside of Boston Public Garden. Stop there for a beer on the way to Beacon Hill. Or, if you are more of a coffee fan, make a stop at Tatte Bakery and Café in Beacon Hill, a local’s favorite.

Cheers Bar – 84 Beacon St.

Tatte Bakery and Café – 70 Charles St.

16.00 – Beautiful Houses of Beacon Hill

North of the Boston Public Garden is located one of the most beautiful neighborhoods in Boston – Beacon Hill. With its narrow streets, historic homes with intricate iron work and brass door knobs, Beacon Hill is the kind of neighborhood I always imagine mysel living in, if only I had a couple million dollars in my bank account.

You can follow this map for a self-guided tour of Beacon Hill or simply walk around aimlessly – you’ll find gorgeous historic homes at every turn. Make sure you stop by Massachusetts State House, which is impossible to miss thanks to its grand golden dome, and take a picture at Acorn Street, the most photographed street in Boston built of river stones from Charles River.

17.30 – More Beautiful Houses on Commonwealth Avenue

From Beacon Hill head towards Harvard Bridge using Commonwealth Avenue, which starts at the Western edge of Boston Public Garden. Commonwealth Avenue is divided in the middle by a wide greenway, called Commonwealth Avenue Mall with many statues and memorials. The avenue will take you through Back Bay neighborhood that boasts some of the most beautiful houses in Boston.

18.00 – Golden Hour at Harvard Bridge

The Harvard Bridge connects Back Bay neighborhood with Cambridge, MA, and provides gorgeous views of the city. Ideally, you should make it here by sunset to admire Boston skyline at golden hour. But even if you come earlier, the Harvard Bridge offers beautiful views at any time of the day.

Tip: if you have more than 2 days in Boston, I highly recommend exploring Cambridge, MA. I have a one day guide to Cambridge.

19.00 – Fresh Seafood and Wine at Select Oyster Bar

Select Oyster Bar is one of the best seafood spots in Boston located in historic Back Bay. It was named the Best New Restaurant in 2015 by Boston Magazine; Best Seafood Restaurant in 2015 and 2016 by Improper Bostonian; and Best New Wine Bar in America in 2016 by Food and Wine magazine.

The space is small, cozy, and reminds of a bistro. The menu features oysters, crudo, ceviche, and local shellfish, prepared simply to showcase the top quality of local seafood.

Select Oyster Bar – 50 Gloucester St.

How to Spend 2 Days in Boston: Day 2

Neighborhoods: The South End, Back Bay, Fenway

Distance: 5 miles (8 km)

9.00 – Breakfast at South End Buttery

Start the second of your two days in Boston at South End Buttery, a café located in the South End. Their menu features a wide selection of breakfast items from muffins and croissants, to sandwiches and burritos, to oatmeal and yogurt parfaits.

South End Buttery is also one of the filming locations for Academy Award winning movie Spotlight. In the movie, the Boston Globe journalist Sasha Pfeiffer (played by Rachel McAdams) interviews one of the victims in the case she is investigating at South End Buttery.

South End Buttery – 314 Shawmut Ave.

10.00 – Lots of Walking in the South End

The neighborhood of South End was designed from scratch by Charles Bulfinch, the architect who also designed Massachusetts State House and the Boston Common. Despite the name, the neighborhood is not located directly to the south of downtown Boston and should not be confused with South Boston (also known as “Southie”).

The South End is famous for its Victorian style houses, many green parks, and artistic vibes. The SoWa Art and Design District (south of Washington Street) boasts many art galleries, studios, showrooms, and boutiques, as well as events like SoWa Open Market, SoWa First Fridays, and SoWa art walks.

11.00 – Trinity Church, an Architectural Masterpiece

From South End head to Back Bay neighborhood, parts of which we explored yesterday. Stop by Trinity Church on Copley Square built by one of the most famous American architects Henry Hobson Richardson. Known for reinterpreting European forms and styles, Richardson combined Romanesque traditions with his own ideas in designing Trinity Church to create a unique look. American Institute of Architects named Trinity Church one of the “Ten Most Significant Buildings in the United States”.

Tip: you can take a tour of the church interior for $10 per person.

Trinity Church – 206 Clarendon St.

11.30 – Awe-Inspiring Architecture and Cakes at Boston Public Library

Across the road from Trinity Church is Boston Public Library. With 23 million items, including books, maps, manuscripts, and electronic resources, it is the third-largest public library in the United States behind only the Library of Congress in Washington D.C. and the New York Public Library.

The library offers free daily guided tours focused on the architecture of the building as well as the art works inside. Check the information about the tours here. If you are exploring on your own, make sure to visit the magnificent Bates Hall, the reading room on the second floor of the library.

Tip: the Courtyard Restaurant located inside Boston Public Library offers fantastic afternoon tea with a view of the library’s courtyard from Monday to Saturday. I wrote about my experience having afternoon tea at the library here.

Boston Public Library – 700 Boylston St.

12.00 – Italian Foods Galore at Eataly Boston

For those who love Italian food, Eataly is a three-story paradise in Boston’s Back Bay. From Boston Public Library it will take you only five minutes to walk down Boylston Street to get to Prudential Center, where Eataly is located.

You can grab something to go, eat at one of the casual cafes, or opt for a fine-dining experience. Afterwards, wander around 45 000 square feet filled with Italian produce and try not to give in to temptation of buying every single item you see on the way.

Eataly Boston – 800 Boylston St.

13.30 – Slightly Overpriced Views of Boston at Skywalk Observatory

While you are at the Prudential Center, go up to the 50^th floor and check out bird’s eye views of Boston at Skywalk Observatory. The price is pretty steep at $25 per person, but this is the only vantage point with 360-degree views that include Boston’s Hancock Tower, Fenway Park, the Boston Common and Public Garden, the Charles River, MIT, and Harvard University.

Skywalk observatory is the only place in this guide that I didn’t visit personally. But I find it worth mentioning, since Prudential Center is in the guide anyways. If you are not willing to spend $25 for a visit to observatory, check out my budget guide to Boston. There’s an alternative to Skywalk Observatory and you won’t have to pay anything for it.

Skywalk Observatory – 800 Boylston St.

15.00 – Venetian Vibes at Isabella Stuart Gardner Museum

Isabella Stuart Gardner Museum is, hands down, one of the most beautiful museums I have ever been to and an absolute must-do if you have only 48 hours in Boston. It doesn’t look like a museum, but rather like a royal palace. Although it contains beautiful pieces of art inside, people come here to admire the beautiful building itself.

Isabella Stewart Gardner, the creator of the museum, was inspired by Venice and its architecture while working on the project. During her trips to Venice, Florence, and Rome she purchased columns, windows, doorways, and balustrades for the gallery.

Tip: if your name is Isabella, admission to the museum is free.

Isabella Stuart Gardner Museum – 25 Evans Way

18.00 – Dinner, Drinks, and Jazz

After exploring Isabella Stuart Gardner Museum head back to the South End, where we started the day. An Uber ride will be the most convenient way to get there. You can also take orange line in metro. Walking back will take about 40 minutes, but you get to see the city.

When people ask me what my favorite dining experience in Boston was, I always name Kava Neo-Taverna. Surprisingly, the best meal I’ve had in Boston didn’t include lobsters or oysters, but a lot of Greek small plates. Try their feta psiti (feta cheese wrapped in phylo dough and drizzled with honey), gemista (bell pepper stuffed with rice, zucchini, and eggplant), and loukaniko (grilled sausage).

Kava Neo-Taverna – 315 Shawmut Ave.

Afterwards, head for drinks to Wally’s Café, one of the oldest family-owned jazz clubs in the city. It has been in operation since 1947 and features live music every night of the week from 6.00 pm to 2.00 am.

Tip: bring cash since Wally’s Café doesn’t accept credit cards.

Wally’s Café – 427 Massachusetts Ave.

If you want to combine dinner, drinks, and live music, check out The Beehive, also located in the South End. They serve comfort food inspired by the Middle East, Eastern Europe, and America. The drinks menu includes exotic cocktails, beers, and a diverse selection of wines and champagnes. The Beehive features live music that includes jazz, blues, R&B, Latin, and country on a nightly basis.

The Beehive – 541 Tremont St.

What Else to Do in Boston if You Have More than 48 Hours?

If you are staying for more than 48 hours in Boston and looking for other things to do, check out this guide by Our Escape Clause.

If you have an additional day, I recommend spending it in Cambridge, and here’s what you should do there!

Prefer to explore the city with a local guide? You can choose one of the many guided tours: from the whale watching catamaran cruise in the Boston Harbor to Fenway Park tour to a guided tour of the Freedom Trail and beyond.

Where to Stay in Boston?

Luxurious option: Omni Parker House

Food being my focus on any trip, no wonder I first learned about Omni Parker House because of the legendary Boston cream pie. It is here, at Omni Parker House that this popular dessert was created over a century ago! Apart from the pie (which is not really a pie, but a cake), the hotel offers old-world charm, elegance, and convenient central location. 

Unique Quirky Option: The Liberty

Ever dreamed of staying at a jail-turned-hotel? It was definitely never on my list of things to do in Boston, but ever since learning it’s a thing, I can’t help but wonder what that would be like. The Liberty, a modern hotel overlooking Charles River, was once Charles Street Jail, a national historic landmark built in 1851. It costs a pretty penny (which is why it’s been on my wish list for a while), but staying in a former prison would be a cool experience. 

Cozy and Moderately-Priced Option: The Copley House

If you are looking for a mid-range hotel, check out cozy rooms at The Copley House. Located inside a red-brick building in the Back Bay neighborhood, it has distinct Boston vibe. The location is unbeatable, Newbury Street and Boylston Street are 10 minutes away as well as a train station.

Budget option: HI Boston 

If you are looking for something simple during your stay in Boston, a bed at a hostel might be a good option for you. HI Boston located in Theatre district, a short walk from Boston Common, is one of the highest rated hostels in the city. 

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