2 Days in Boston: Your Perfect Weekend in Boston Itinerary

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Wondering how to spend two days in Boston? Relax and enjoy one of America’s oldest cities with this inside guide and two day Boston itinerary.

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How to Spend Two Days in Boston

Why visit Boston?

America may be known for many things but its keen sense of history isn’t always one. Not so in Boston, where the Freedom Trail highlights 16 landmarks on the road from the Tea Party to the first reading of the American Declaration of Independence.

But it’s not all serious stuff.

Boston also houses the country’s oldest baseball stadium and you can sleep right next door, in a memorabilia hotel that lets you spin your own vinyl and lounge on rock star yellow sofas.

And old is becoming new again in the Sowa district, where Sundays are spent learning to paint, chatting with artists, drinking craft beer and mingling through pop-up coffee shops and vintage markets.

In short, it’s an exciting city. Here’s our inside guide and your 2 day Boston itinerary.

Where is Boston?

Located on the north-eastern coast of the United States, the cosmopolitan city of Boston is a central historic site for the history of the American Revolution and home to two of the most famous universities in the world: Harvard and MIT.

If you are taking a city break in Boston, planning is everything. The city is so rich in tourist attractions, ranging from historic buildings to century-old restaurants and picturesque neighbourhoods, that it is impossible to explore them all. But with our 2-day Boston itinerary, you can see a bit of everything and discover the city’s vibrant art scene without feeling overwhelmed. You just need to put on some comfy shoes!

How to Get to Boston

The city is well connected to most states in America, as well as to several countries abroad. Depending on your budget and preferences, you have four main ways of travelling to Boston:

  • By plane: Boston Logan International Airport is the main airport that serves the city. It has flights to and from numerous destinations, both domestic and international. From the airport, you can take a taxi, ride-share, or use public transport to reach the city centre. You can reserve a GO Boston Shuttle online. However, keep in mind rush hour traffic (usually during typical commute times from 7-9am and 4-6pm) which can make travel time increase significantly. If you arrive during rush hour, the best option might be to take public transportation. It’s free to ride the Silver line when inbound from the airport, but keep in mind that you’ll need to pay the fare when returning to the airport.
  • By train: The city’s two main train stations, South Station and North Station, serve as hubs for Amtrak and other regional trains linking Boston to the main cities in the US.
  • By car: Several major highways run into Boston, including the I-90, I-93, and I-95.
  • By bus: If you want to save money, several major bus companies, including Greyhound and Peter Pan, offer frequent services to and from nearby cities and states.

How to Get Around Boston

Once in town, you have several options for getting around. To save time, money, and energy, you will quickly learn that it’s best to combine them depending on where you need to be.

  • Public Transportation: The Massachusetts Bay Transportation Authority (MBTA), also known as the “T”, operates bus, subway (the “Red Line” and “Orange Line”), and commuter rail services in the city. It is affordable, and you may need to use it sometimes if you plan on heading far from the centre. The Charlie Card is available to get and reload money on to make traveling quicker. They’re available at every subway stop and free to get. Fares are also cheaper when you use this card, about $2.25 one way.
  • Taxis and Ride-Sharing Services: Uber and Lyft are readily available in Boston, making it easy to get around the city, especially for short trips.
  • Walking: Many of the city’s most famous landmarks and attractions are within walking distance of each other. Like New York, Boston is a walkable city, but it doesn’t experience the same fast-paced atmosphere during rush hours.
  • Driving: If you choose to drive in Boston, be prepared for heavy traffic, narrow streets, and parking challenges. It is, in fact, the last option you would want to choose.
  • The Go Boston Card is a card available for purchase that is like an “all inclusive pass” to visit attractions in Boston. Depending on what you want, the prices vary but it can be a way to save money on transportation and activities. 

When Is the Best Time to Visit Boston?

Spring in Boston is marvellous, with flowers and trees blooming everywhere. The sun is still shy, but the frost has definitely gone by March, and outdoor events begin to take place around the city. This is possibly the best time of the year to visit Boston. You will avoid the crowds and be able to walk around without wearing three sweaters and a coat, which are essential during winter. Autumn is also a magnificent time to visit but keep an eye on the weather forecasts for rain.

Winter in Boston is icy and snowy and summer brings not only sunshine but fairly fierce humidity. In short, Boston is interesting to visit at any time of year but the four seasons make themselves known at each and every point.

Overlooking Boston and its boutique hotels from the Skywalk Observatory
You can see a lot of Boston in just two days…

Your 2-Day Boston Itinerary

Spending a weekend in Boston is a great way to learn more about American history, art, and gastronomy, all with cool hipster vibes.

Day 1 in Boston

Reserve your first day in Boston for the most important landmarks. You can explore the town on your own or book a guided walking tour with a local. We recommend the second option – you will learn so much more. Then, there’s also the much loved trolley tours, another way to see Boston.

Delve into the Museum of Fine Arts

The Museum of Fine Arts houses over 450 000 works including paintings, sculptures, photographs, drawings, and prints, some dating back to ancient times. You won’t have time to see everything, so focus on its best sections. This is the perfect place to admire a Monet and also to immerse yourself in the art of the famous Japanese artist Hokusai.

Take a Stroll through the Boston Public Gardens

If it’s spring or autumn outside, you mustn’t miss the Boston Public Gardens. The first public botanic garden in America, it consists of 24 acres of land covered in flowers and trees arranged around a lovely pond with swan boats. It is a great place to connect with nature and watch Bostonians walk their dogs or rest on benches in the sun.

Snap a pic of the famous Make Way for Ducklings statue and keep strolling around until you feel you deserve a nice warm lunch.

Explore the Freedom Trail

One of the most important tourist attractions in Boston is the 2.5-mile-long trail, also known as the Freedom Trail which connects 16 historic sites related to the American Revolution. Spend the afternoon with a local guide or on your own, hopping from one historic building to another and getting to know more about the founding of the United States.

The Freedom Trail walking tour runs through downtown Boston and is marked by a red line. You probably won’t be able to see all the sites in one afternoon, so try to focus on the buildings you find most interesting. Here are some suggestions:

  • Boston Common – this is the oldest public park in the United States and the starting point of the Freedom Trail. One of the main attractions is the large pond, perfect for duck watching.
  • The Massachusetts State House – one of the most recognisable buildings in Boston due to its large golden dome, the State House is open to the public, offering several museums and exhibits, as well as a mural depicting the history of Massachusetts and a statue of founding father Samuel Adams.
  • Park Street Church – the oldest and most well-known building in the city was built in 1809, so long after the American Revolution. However, it was here where William Lloyd Garrison gave his first antislavery speech, and the hymn “America” was sung for the first time.
  • Granary Burying Ground – this is one of the oldest cemeteries in Boston, dating back to 1660. Many tourists include it on their two day itinerary for the beauty of its monuments, burial sites of some of Boston’s most prominent citizens. It can feel strange to stand next to the graves of Samuel Adams and Paul Revere.
  • King’s Chapel – a centre of Tory sympathies during the revolution and briefly occupied by the American troops, King’s Chapel is today the oldest continuously used place of worship in the city. It is a great piece of Georgian architecture and has excellent acoustics, making it a popular venue for concerts.
  • Old South Meeting House – for a long time, the Old South Meeting House was the largest building in colonial Boston and a centre for the political and social activity in the city. It hosted several important events during the revolution, including the planning of the Boston Tea Party in 1773.
  • Old State House – the centre of political power in colonial Boston, the Old State House served as the site for several key events during the revolution. It’s also the Boston massacre site, and conflict between a local crowd and British soldiers which took place in 1770.
  • Faneuil Hall Marketplace – also known as the Quincy Market, it consists of several historic sites, including the Faneuil Hall itself, an important meeting point for politicians and merchants in the 18th century. The market bursts with restaurants, so it is a great place to grab a snack and take a break.
  • The Paul Revere House – located in the North End neighbourhood of Boston, it is the oldest surviving structure in downtown Boston and was the home of American revolutionary Paul Revere from 1770 to 1800. It is a typical example of an early American colonial building and was recently restored to its original appearance.
  • Old North Church – established in 1723, this is one of the oldest churches in the United States and is best known for its role in the start of the American Revolution. On April 18 1775 it displayed two lanterns, which announced to the revolutionaries that the British were coming by sea.
  • The USS Constitution Museum – make the Boston Harbour your next stop to discover the oldest commissioned warship still afloat in the world. Today it houses a floating museum dedicated to the ship and the people who served on it.
  • Bunker Hill Monument – end your walk in the wonderful Charlestown neighbourhood, where you can admire a 221-foot-tall monument. The Bunker Hill Monument is a granite obelisk erected to commemorate the people who died in the Battle of Bunker Hill.

Don’t forget to check out our east coast road trip from Boston itinerary as well.

Exterior shots of Sowa Market in Boston as part of a two day Boston itinerary

Day 2 in Boston

On your second day in Boston, you will discover that there are still lots of places you could visit and so little time. This is why we included more attractions on the list, leaving it to you to choose and combine.

Visit the MIT Museum

If you think of yourself as a secret (or not so secret) geek, then checking out the MIT Museum is probably one of the best things to do in Boston. It sits, in fact, in Cambridge, Massachusetts, rather than Boston but it is only 13 minutes away with the T.

Reserve enough time to discover the history and culture of MIT and to learn about its contribution to science. You’ll find lots of photographs and artefacts here and will either leave inspired – or a little overwhelmed.

Explore the Harvard Museum of Natural History

The Museum of Natural History, belonging to Harvard University, is a big attraction for nature lovers who want to learn more about botany, geology, and zoology. Walk along the large halls and rooms that hold the vast collection of specimens from around the world.

The stars of the museum are the Great Mammal Hall, the huge collection of Blaschka Glass Flowers, and the Wright Hall of Fossils.

If you are bringing the kids, there’s plenty for them as well. The museum offers several interactive exhibits, a large dinosaur cast, and even a live beehive.

Discover the Art Collection at the Isabella Stewart Gardner Museum

If you fancy art museums, head to the Fenway neighbourhood, where you will find a spectacular building designed to resemble a 15th-century Venetian palace. It was founded in 1903 by Isabella Steward Gardner, a leading American art collector and philanthropist.

Today, it hosts over 2,500 works of art, including paintings and sculptures but also decorative objects and textiles from America, Asia, and Europe. The collection is exquisite, allowing you to admire some of the works of Degas, Botticelli, Michelangelo, and Rembrandt right in the heart of Boston.

Fall in Love with the Boston Public Library Building

An art piece itself, the Boston Public Library is one of the oldest and most well-respected in the United States. The main branch of the library is the McKim Building, a place described as a “palace for the people” in 1895 when it opened. The library has an impressive collection of over 23 million books, manuscripts, photographs, and maps and attracts many tourists every year. It is free to visit, so do go inside for a feast of the eyes and mind.

Say Hi to the Sea Turtles at the New England Aquarium

For a magical marine life experience, spend an hour at the New England Aquarium, a huge home for sea mammals, birds, reptiles, and fish. Sit on a bench under the glass ceiling and watch the sharks sliding above you or come nose to nose with a catfish.

Head on to the Giant Ocean Tank for a close look at the corals living here, and don’t leave before greeting the African penguins at the Penguin Colony section.

Abigail King in Boston taking a scenic boat tour along the Charles River
Taking a scenic boat tour along the Charles River

Take a Scenic Boat Tour along the Charles River

When your feet start to hurt, hop on a boat and take a tour along the Charles River from Boston Harbor. It’s surprising how soon soon you can see the city’s skyline, passing by the Charles River Esplanade and Dam and seeing the cool streets of the Back Bay neighbourhood from the water.

Taste a Bit of Europe in Little Italy

As the evening settles in, take a T to Boston’s north end for a romantic evening in its Italian-American neighbourhood. There’s a different vibe here, in between the narrow, winding streets, edged by beautiful brick buildings and lots of cafes and restaurants.

Boston old and new eating hipster food in Back Bay Boston
You’ll find plenty of gorgeous bakeries and eateries in Back Bay, Boston

Where to Eat in Boston

You can find almost anything you want to eat in Boston, with a mix of restaurants, that combine American cuisine with Italian, French, and Chinese dishes.

But if you’re new to America, it’s fun to try out some burger bars where fast food is taken seriously. Another lovely way to spend a lazy Sunday involves checking out the food stalls at Sowa Market.

Recommended eateries:

  • Union Oyster House – eat in an historic location in operation since 1826. The Union Oyster House is one of the oldest restaurants in America and is still serving the classics: baked haddock and clam chowder. With its classic décor and warm atmosphere, it does make you feel like you are dropping into an inn in 19th century Boston.
  • Mike’s Pastry – one of the most famous pastries in town for its long tradition and delicious cannoli, Mike’s Pastry is worth at least one visit whilst in Boston.
  • No. 9 Park – for an exquisite French experience, explore the beautiful Beacon Street and then stop at this bistro in Beacon Hill. It is the best place to pair gourmet dishes with expensive wines.
  • Neptune Oyster – while in North End, grab lunch at this tiny seafood eatery. It serves large portions of lobster rolls and fresh oysters. Sooo delicious!
  • Oleana – if you decide to visit either the MIT Museum or Harvard Museum of Natural History on your second day, stop by this lovely restaurant in Cambridge. The menu is inspired by Mediterranean and North African cuisine and is a nice alternative to the heavy American dishes.
  • Myers + Chang – a quirky Chinese restaurant in the south end, Myers + Chang serves high-end Asian food and offers a delicious selection of cocktails. It is the perfect choice for a night out on a weekend Boston itinerary.
Abigail King mingling with artists in Sowa Boston
Exploring the cool vibes around Sowa Market

Adding More to Your Boston Weekend Itinerary

When it comes to what to do in Boston, the places and experiences in Boston never seem to end. In fact, you may need a year to see everything. But, if you can stretch 2 days in Boston to have one more day, here’s what you can make of your long weekend in Boston.

Sowa Market – here, more than 100 artists work in renovated warehouses, creating paintings, ceramics, couture and cut-outs, and throwing their doors open on a Sunday morning to a decidedly hipster-cool crowd.

Around 20 food trucks rock up each week to 540 Harrison Avenue to serve organic eats and smoothies next to grilled cheese and brick oven pizza beneath strands of baubly lights.

Take lots of pictures on Acorn Street – this is the most picturesque street in Boston. Cobbled and winding, full of small shops and restaurants, it is very popular on instagram.

Stop by Trinity Church – you may recognise this church from the movie The Boondock Saints, and, indeed, its exceptional interior is hard to forget. It is one of the oldest churches in Boston and is considered a jewel of the city, so make sure to stop at Copley Square for a few minutes to gaze at its splendid façade and discover its interior.

Red Sox Boston Fenway Park exterior shows America's oldest baseball stadium as part of a weekend Boston itinerary
Visit America’s oldest baseball stadium as part of a weekend trip to Boston

See Fenway Park – America and baseball have what I suppose we’d call as special relationship, but in this case, Fenway Park is even more special than most.

It’s the country’s oldest stadium, dating back to 1912 before there’d even been a world war and with seats that were set in somewhere between the first and second.

If you can’t get tickets (or if you’re with a young child and it isn’t a good idea) then hanging around the area soaks up plenty of the Boston Red Sox vibe.

For processed and polished facts and lashings of fun trivia, book a guided tour of the stadium. (You can catch an inside glimpse of Fenway Park on the broadcast here.)

Learn More about the American Revolution at the Boston Tea Party Ships & Museum – after you visit the USS Constitution Museum, stop by this museum as well to hear the story of the Boston Tea Party and learn more about the events that led up to the American Revolution.

Discover the New England Holocaust Memorial – this is a monument dedicated to the 6 million Jews who were killed by the Nazis during WW2. It is a glass building with many symbols designed to make visitors reflect on what happened and acknowledge the gravity of the past.

The Skywalk Observatory – this observatory provides a 100 mile radius view of the present if you look one way through the glass. If you turn around, you’ll see a view of the past, as the museum explores how vital immigration has been and continues to be to be in Boston.

Where to stay during 2 days in Boston

A good night’s sleep can make the difference between a successful vacation and an average one. Fortunately, Boston offers a wide range of accommodations to suit different budgets and travel styles, so you just need to pick the one that fits you.

Here are some recommended places to stay in Boston:

  • The Ritz-Carlton – located in the middle of things, this luxurious hotel has a full-service spa and fine dining options.
  • The Mandarin Oriental – a 5-star hotel located in the Back Bay neighbourhood with an indoor pool, full-service spa, and multiple dining options. The Mandarin Oriental is a good place to stay if you want to be close to the river.
  • XV Beacon – this chic hotel in Beacon Hill has a restaurant, rooftop terrace, and personalized service. It is the ideal place for families due to its generous rooms, and if you are travelling with your pet, you can be sure it will be well treated here.
  • The Eliot Hotel – a historic hotel located in the Back Bay, the Eliot attracts lots of customers with its full-service spa, 24-hour fitness centre, and in-room fireplaces. It offers plenty of options for families and serves a delicious breakfast.

And some cool and unusual places to stay in Boston…

The Verb Hotel

Described as “Boston’s most radical, retro, rock-and-roll hotel,” The Verb hotel seems to sum up the city’s love affair with the past and thirst for the future.

For this is a living museum. Not to the founding fathers of the republic but to the founding fathers of rock and roll. Black and white photos of a young Elton John, Mick Jagger and Johnny Rotten grace the walls. A vinyl library supports the record player in every room and even the toilet roll holder says Rock ‘n’ (extra) Roll.

What made the place more than just a kitsch distraction on this long road called life was the mixed in, in-the-minute cheers from the neighbouring stadium Fenway Park.

2 days Boston itinerary place to stay - the Fairmont Copley Plaza interior shot with dog
Family travel in the glamorous and well located Fairmont Copley Plaza Hotel

The Fairmont Copley Plaza Hotel

With gilded corridors criss-crossing the lobby and an unquestionably stately address, The Fairmont Copley Plaza Hotel almost qualifies as an historic institution in and of itself.

(It is actually a member of Historic Hotels of America®, the official program of the National Trust for Historic Preservation for recognizing and celebrating the finest historic hotels across America.) It’s just steps away from the iconic Boston Public Library and only a few steps more to some highly instagrammable bakeries and bars of Back Bay and Beacon Hill.

Since 1912, the Fairmont has ushered luxury through its heavily carpeted lobby but unlike many other grand landmark hotels, you’ll find a canine ambassador as part of the arrival process too.

Or in other words, a friendly dog will greet you in the lobby.

The Liberty Hotel

After a chic and leafy walk through Beacon Hill, you’ll find the Liberty Hotel.

It’s easy to believe that in Boston, this name should signify some great part of the story that became the American dream.But, somewhat subversively, it’s a boutique hotel that used to be a prison instead. A very cool and unusual place to stay and in a great location for any 2 day Boston itinerary.

So, can you see Boston in a weekend?

As this Boston 2 day itinerary shows, you can’t see the whole city in a simple Boston weekend trip.

But, you can manage to see the top things to do in Boston and have a wonderful time in the process.

I’d highly recommend using Boston as a base for a road trip through New England to compare and contrast the red brick city life with the bright white picket fences of the green surrounding countryside.

FAQS about Boston in 2 days

If you’re thinking of heading to Boston for the weekend, then check out these FAQs. And then enjoy our 2 days in Boston itinerary!

Is 2 days in Boston enough?

Two days in Boston is plenty enough to have a great weekend seeing historical sites, cool eateries and outdoor spaces. However, it’s not enough to see the whole city.

How many days do you need to see Boston?

To see the whole city, you probably need 5-7 days. However, even if you only have one day in Boston, I’d definitely recommend going. It’s a world class, fascinating city.

How about 2 days in Boston in the fall?

New England is at its prettiest in the fall (or autumn) and so if you’re planning a trip to Boston as a springboard for a road trip into Massachusetts, then this will be a dazzling time to visit. However, bear in mind that prices shoot up at this time and accommodation becomes scarce.

Keen to travel further afield but unsure where to go? Check out our guide to choosing between Los Angeles and Miami.

More on Travel in New England

Disclosure: some hotels I paid for myself, for others I was hosted. But the important point is this: I always keep the right to write what I like here on the blog and only recommend things I think are worth recommending for the reasons I recommend them. Because, life is too short otherwise!

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6 thoughts on “2 Days in Boston: Your Perfect Weekend in Boston Itinerary”

  1. i am new in boston, few days ago i just came here for 10 days trip, and looking for boutique hotels. Thanks for sharing the info.

  2. Boston is such an awesome city! We spent a weekend there last year and loved it. We weren’t lucky enough to stay at any of the hotels you talk about in this post, but I could quite easily book a room in the Fairmont – in fact, I might now I’ve seen the photos! Sadly, it won’t be yet as are heading to Antigua next month.

    • Ah, yes, the Fairmont was a real treat. SUCH a great location too. And, yes, Boston has so much to offer. There aren’t many cities I’d go back to again and again but Boston is definitely one of them. Enjoy Antigua !

  3. Going to Boston at the end of the month, so finding this post was quite timely! Thanks for sharing – each of these places look very cool and unique, going to check them out now!

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