Boston in 2 days – itinerary and guide I wish I read

As a person who spent most of her life in Europe, shifting to the USA brought so many contrasts to my life – different food habits, culture (yes, despite being home to so many immigrants – there are distinct cultural norms and habits that you need to get used to), shopping style, transportation system – you name it. It’s not better or worse – it’s just different.

Boston was the first city I’ve visited that brought me a homey feeling. As a European, one of the main challenges I face in the USA is the need for a car and a driving license. One of the reasons I fell in love with Boston – it is such a pedestrian-friendly city! You have many areas built for people there – from spacious walking streets to parks and other public spaces in the town.

Boston is also home to so many Universities that’s why there is a very thoughtful vibe of intellectual curiosity and innovation. You will constantly find many interesting events.

This is also the first city where past and present blend seamlessly through many neighborhoods and cultures. I’ve spent almost two weeks in the city, and if I had to plan two days in Boston, here is how I would do that.

First, I’m making a few basic assumptions:

  • You will have two full days in Boston – honestly, you’ll easily find how to fill your days with something interesting even if you stay a week.
  • You enjoy exploring culture, arts, and music as my recommendations are more skewed towards those. I’ll write a separate post about interesting events and places I’d visit to explore the culture and musical side of the city.

Just for the record, in my opinion, you need to spend 4 days in Boston to explore the main points of interest. So if you have more time, you’ll definitely find how to plan out an interesting journey.

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First Day in Boston

Boston Common
Boston Common

Boston is a city characterized by its diverse and distinctive neighborhoods, each with its own unique charm and atmosphere. Back Bay, North End, Fenway-Kenmore, South End, Seaport, Charleston – you name it. The first day I would recommend that you spend walking around various neighborhoods.

  • Start your day by visiting the historic Freedom Trail.
  • Natalia, how about the coffee?
  • Fair enough! Sure, Boston has plenty of famous cafes, you can start your day at Tatte Café – you’ll find there both coffee, bakery, and some breakfast menu. Though I do not classify myself as a foodie, working with a FoodTech startup for four years, living in India for a few years, and my Eastern European origin left an impact on how I choose and recommend places. Tatte is on my recommended list!

Freedom Trail

Freedom Trail will immerse you into the history and heritage through the events and places that played important role in America’s history, revolution, struggle for independence, the birth of a nation, and the ideas that shaped the United States.

You can explore the trail by yourself or you can take a guided tour – there are free walking tours – they can be tip-based and paid. I’ve experienced one with the Freedom Trail Foundation. Here are the places in Boston they will cover: Boston Common, Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel, Benjamin Franklin Statue, Old Corner Bookstore, Old South Meeting House, Old State House, Boston Massacre Site, Faneuil Hall. I’ve visited Charlestown separately.

Personally, I found it interesting, but it was quite fast-paced and covered only the Boston part. Though given time constraints, they do a great job of presenting a lot of information in an engaging way. I would recommend bucketing another couple of hours after the tour if you are planning to enter/visit any of the sites you’ll see during the tour.

Logistics:  Cost: Adult – 17 USD, Student – 15 USD, Child – 5 USD.  Duration: 90 minutes. Book here.

Boston city streets
Boston streets in summer

Another popular choice to explore the city is to do a Duck tour – that traverses on both land and water. I haven’t personally taken it, but I’ve seen plenty of duck cars moving around the city while I stayed in Boston.

You can have lunch in the Faneuil Hall area – there are several markets with numerous cafes in the same area. I come from a “soup for lunch” region so I’ve taken Clam Chowder (it’s a thing in Boston), but you’ll find all possible meal options for any taste and budget there.


After lunch I’d proceed to Charlestown – it’s one of Boston’s oldest neighborhoods, founded in 1628. It played a key role in the American Revolution and boasts a wealth of historic sites and landmarks that reflect its colonial heritage. Here are the last two points on the Freedom trail – Bunker Hill Monument and USS Constitution Museum.

The USS Constitution, also known as “Old Ironsides,” is one of the oldest commissioned warships afloat. It has a storied history, including victories in the War of 1812. Visiting the museum allows you to connect with its rich history. It offers interactive exhibits and displays that provide a hands-on learning experience. Visitors can learn about life on board the ship, naval battles, and the ship’s role in American history. The museum houses a collection of artifacts, including uniforms, weaponry, and personal items that belonged to sailors who served on the USS Constitution. The museum is very kid-friendly and has many games and interesting ship activities.

Museum Logistics: hours: 9 to 6 PM; Timing: 1-2 hours; cost: free of charge by considering donating. You can also visit the ship. Though it is well maintained, it contains roughly 15% of the original wood. Please note that you’ll need to carry your ID if you want to visit the ship. Read more information on the USS Constitution’s official site.

I’d say you need to make a call between USS Constitution and Bunker Hill, as they both work till 5-6 PM. I loved that Charlestown is located along the waterfront and it offers beautiful views of Boston Harbor and the skyline. It’s a great place to take a walk and enjoy the scenic surroundings.

North End

North End Green Building street
One of the streets in North End. Do not miss bakeries in this neighborhood)

In the evening, if you still feel power in your legs, head to explore the North End Neighborhood.

The North End is a historic neighborhood in Boston known for its Italian heritage, charming streets, vibrant culture, and delicious food scene. It’s one of the city’s oldest neighborhoods and offers a unique blend of history, community, and culinary delights.

Start your exploration by taking a leisurely stroll through the narrow, cobblestone streets of the North End. Admire the well-preserved 19th-century architecture, colorful facades, and charming gardens. The North End has a distinctive European feel that sets it apart from other Boston neighborhoods.

From historic sites, you will see here Old North Church, Paul Revere House, the oldest house in downtown Boston, and learn about the life of the famous patriot.

Plan your dinner here. The North End is renowned for its exceptional Italian food. Be sure to indulge in some authentic Italian cuisine, whether it’s a traditional plate of pasta, a delicious pizza, or a savory calzone. If the weather is nice, walk along the waterfront and enjoy the beautiful views of Boston Harbor.

Second Day in Boston

If you feel the crave to visit a museum in Boston, there are plenty of places. But if I had to recommend something unusual, that would be Isabella Gardner’s museum. It stands out for its eclectic collection, stunning architecture, and the visionary spirit of its founder. Isabella Stewart Gardner is a remarkable woman with a passion for art and culture, and I can’t deny – a very privileged person, but this museum is more about the story.

Isabella Stewart Gardner’s collection is diverse and spans different cultures, time periods, and artistic mediums. It includes paintings, sculptures, decorative arts, furniture, textiles, manuscripts, and more. The collection features works by renowned artists like Rembrandt, Vermeer, Botticelli, and John Singer Sargent. But it’s more about how she arranges them and the story of each space. If you want to visit a place with a meaning, this is it.

What to know about visiting Isabella Gardner’s museum:

  • Cost: 26 USD for adults, 13 for students, 6 for kids.
  • I recommend booking the tickets in advance – you can do it on the official website . There are situations when you might not get tickets on the spot since it’s a popular museum.
  • There is a free audio guide that you can follow on your phone – just take the headphones with you.
  • I did a full audio tour at a quite relaxed pace and it took approximately 2 hours and 15 minutes.
Isabella Gardner Museum Boston
Isabella Gardner Garden

Back Bay

From Isabella Gardner Museum I would head to the Back Bay neighborhood.

Back Bay is a vibrant and upscale neighborhood located in the heart of Boston, Massachusetts. It’s known for its iconic Victorian brownstone buildings, fashionable shopping streets, cultural institutions, and a mix of historic charm and modern amenities. Some of the Streets and destinations to explore:

  • Newbury Street is particularly famous for its charming architecture and upscale boutiques. It is a premier shopping destination in Boston. The street is lined with a variety of shops, including high-end fashion boutiques, art galleries, and specialty stores.
  • Beacon Street is one of the most historic and prominent streets in Boston, Massachusetts. It stretches for several miles, passing through various neighborhoods and offering a mix of historical sites, charming architecture, and cultural landmarks.
  • Copley Square is a bustling square at the heart of Back Bay and features some of the neighborhood’s most iconic landmarks. The Boston Public Library’s main branch, Trinity Church, and the John Hancock Tower are all located around Copley Square.
  • Boston Public Library – it is so impressive, do not miss it. The Boston Public Library has a long history dating back to the mid-19th century. By visiting, you’re stepping into a space that has been an important part of Boston’s cultural and educational landscape for generations. I’ve spent in the library around one hour. Do not miss the painting exhibition on the second floor.
  • Prudential Center: is a large commercial complex that includes the Prudential Tower, one of Boston’s tallest buildings. The complex features a shopping mall, dining options, and the Skywalk Observatory, which offers panoramic views of the city.
  • Take a leisurely stroll along the Charles River Esplanade, a picturesque park along the riverbank. It’s a popular spot for jogging, picnicking, and enjoying the scenic views of the water and the city skyline.

Back Bay offers a diverse range of dining options, from upscale restaurants to casual eateries. You’ll find a variety of cuisines. Since Boston is famous for seafood, I can personally recommend Salty Girl.

The experiences above I would totally do in Boston in a weekend again to get a feel of the city. I’d like to leave the second half of the day for things you would enjoy, and I’m gonna share with you a few options:

  1. Explore Cambridge – Cambridge is just one bridge away from Boston, and it’s home to MIT, Harvard and other institutions. Those Universities also have a few museums. I’ve visited Harvard’s Glass Museum and found it interesting. You can also stroll along the river, visit the main square with small picturesque streets, and have dinner in one of the popular restaurants.
  2. Head to East Boston and Lo Presti park – situated across the Boston Harbor, East Boston, also known as “Eastie” is a different cute neighborhood and a very beautiful skyline opening from Lo Presti Park. There are plenty of food places including a very popular Tall Ship but the queues there in the evenings can get massive.
  3. Watch a game at a Fenway park – it is an iconic and historic baseball stadium – one of the oldest Major League Baseball stadiums still in use, with its inaugural season dating back to 1912. Home to the Boston Red Sox, the park has witnessed countless baseball legends and memorable games. If you choose this option, it’s very close to Isabella Gardner museum if you want to optimize your route.

Please note, any of the options suggested above will take you roughly half of the day.

Boston skyline location
Boston Skyline from Lo Presti Park

What to pack to Boston

Do not trust your favorite weather website. The weather changes often in Boston and even if prognosis promises a sunny day, you might notice clouds gathering in a couple of hours and maybe a light rain.

I’m sharing items that you need to bring in addition to your regular clothing and items you carry with you.

Definitely bring an umbrella and raincoat and I recommend carrying a raincoat with you. I have a Columbia raincoat and a very sturdy umbrella that survived several rough Upstate New York winds. The manufacturer offers 10-year warranty, though I didn’t need to replace it so far.

Sun Protection: If you’re walking the trail in the sunny weather, wear sunscreen (It’s a personal choice – I use Dr Ceraucle Regen Vegan Sun SPF 50 PA ++++. It doesn’t clog the pores, and has nice ingredients), a hat and sunglasses (if you are traveling in summer, and something woolen if in winter). Boston gets quite a high UV index in summer days and a lot of sun (for the North East Standards).

Comfortable shoes – you will need to walk a lot on different surfaces. I feel for all the seasons I bounce between Rieker and Remonte and can’t recommend them enough. I’ve been wearing some of their shoes for over five years, and they have special lines for anti-stress shoes which are so soft and comfy.

Hoodie – even if you visit in summer, bring warm clothes. While it’s mostly warm outside, in many commercial spaces people go a bit fanatical about the AC.

How to commute in Boston:

There are so many ways to get around Boston from public transport to Hop on/Hop off tourist buses that you can take for a day:

  • Boston by public transport: Boston has an excellent public transportation system, known as the “T” (short for MBTA). Use the subway (known as the “T” subway system) and buses to get around the city conveniently. Consider purchasing a CharlieCard or a CharlieTicket for easy access to the transit system. It is historical and nice to experience (once), but for longer distances, it is so slow. On stations where you need to enter underground – take care to take the right entrance. If you take the wrong one, there is a workaround to go + – one station as not every station allows you to go to the other side without exiting.
  • Boston by bicycle: Boston is one of the few cities in the US where you can ride a bicycle in dedicated bike lanes. For this, download the Bluebikes APP. You’ll find locations with the bikes on the map – when you register, I recommend against using Apple Pay. They charge you when you unlock the bike, but the system can fail to charge you at the end of the journey if you spend more time biking than you initially paid for. As a result, your account can be blocked and you’ll spend quite some time talking to the customer service trying to understand what went wrong. The cards worked perfectly fine for me.
  • Uber is relatively affordable if you need to travel somewhere at odd hours.
  • Walk: Boston is a pedestrian-friendly city, especially in its historic neighborhoods. Bring comfortable walking shoes to explore the town on foot.

What else?

Boston in two days detailed guide
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  • Boston is truly incredible, don’t rush through it, stroll through the streets, and envision how revolutionaries like Paul Revere, literary giants such as Edgar Poe, and other creative minds roamed through these avenues.
  • Try to choose accommodation closer to the central area if you find good deals. I’ve recently started using more AirBnb over Booking (, but check both. Boston is relatively small and walkable.
  • I would say that the two days in Boston I described are more on the active side of traveling – lots of walking and exploring. They are doable, but if you visit during the warm weather when it’s pleasant to be outside, I would spread the plan above across three days. Everything above you can visit even faster than I suggested, but probably you’ll like a peer where you’d want to hang out just for a while watching seagulls and the skyline, probably you’ll fall in love with one of the numerous parks and would like to chill there for an hour, or you’ll discover a very cute café on one of the old streets where you’d like to take a break. These moments make the travel a more memorable experience.
  • Consider stopping by a visitor center: Boston Common Visitor Information Center or the Faneuil Hall Visitor Center to gather more information about the city and get any questions answered.

I fell in love with Boston and hopefully you will too. Have a wonderful journey!

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