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2 Days in Boston – Weekend in Boston Itinerary

By 21 August 2018 September 17th, 2021 No Comments

Planning a weekend trip to Boston and looking for an easy 2-day itinerary? You’re in the right place!

Boston is a city filled with so much history, stunning architecture, culture, and uniqueness which will surely amaze you. It’s also home to two of the United States’ most prestigious universities; Harvard University and Massachusetts Institute of Technology (MIT). So for all of you who’re into the academe, Boston is also a place that’ll surely spark your interests!

I visited Boston over a weekend not expecting to be too impressed, but I was pleasantly surprised at how much I loved this city. I had such a fantastic time spending a weekend in Boston, and so Boston undoubtedly became one of my favourite cities in the USA to spend over a weekend.

My love for the city is what spurred me to create a two-day itinerary for the ultimate weekend in Boston. My itinerary consists of a map which includes destinations such as restaurants, historical sites, parks and so much more.

Boston is a city where you’ll never run out of things to do, but if you only have 2 days to spare then that’s fine as well. This city will welcome you in its arms and you’ll feel like you never want to leave.

If you’re planning the perfect weekend trip to Boston, then keep reading to uncover the best of Boston in 2 days – you’ll find some fun activities to do for the coming weekend!


As always, I find the best way to source for the cheapest flights is by checking on Google Flights & Skyscanner.

As for accommodation, I found Booking & HotelsCombined to provide the most comprehensive, unbiased comparison of different hotel sites. 

I travel long-term and never leave home without Safetywing, an affordable nomad travel insurance that covers COVID-19 too!.

Note: We did a LOT of walking so make sure to bring some comfy shoes if you’re following this itinerary. The only area we did not walk to was the Sam Adams Brewery Tour.

2 Days in Boston, weekend in Boston itinerary

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When to Visit Boston?

Generally, summer and fall are the perfect times to visit this spectacular city, although Boston is quite beautiful all year round.

Hence, plan your visit when you actually have the time to do so!

How to Get from the Airport of Boston?

If you’ll be flying in from a place further away, then you’ll surely land at the Boston Logan International Airport.

The airport is about 5 miles from Downtown Boston and if you’ll be driving by car, it’ll take you no more than 15 to 20 minutes (depending on the traffic that day).

There are different modes of public transportation for you to hop onto if you don’t have a rented car at the ready.

Obviously, there are the ride services like airport taxis, Uber and Lyft and these usually can cost a bit more than the train. Bear in mind that this is a better option for you if you’ll be arriving in the wee hours or if you have a bit of luggage with you.

However, the train is pretty handy and it’s connected to Boston’s train system, which makes it all the more accessible! Plus, it’s so much cheaper than those ride shares…

How to Get to Boston?

If you’ll be coming from another state or another city in the United States, then you can easily get to Boston via the Amtrak train or the Greyhound bus. Although if you’ll be coming from a further distance, then it’s best to fly in to Boston Logan International Airport.

How to Get Around Boston?

There’re so many public transportation options in Boston – taxis, Uber and the famous Massachusetts Bay Transportation Authority (MBTA).

The MBTA is also the main public transport that you’ll be using to get around the city. It’s very easy to use and just like most subway systems, you only need to get a card called the CharlieCard.

A one-way fare is $2.40 but if you’re going to be running around the city, then it’s better to get a one-day pass for $12.75.

What is the Boston Go Card?

If you’re thinking about going out and about in Boston, then it really is best to purchase a Boston Go Card. This includes all-in access to 45+ local attractions in the city. You can even claim it digitally so you wouldn’t need to have it printed out.

You can choose from an All-Inclusive Pass, Explorer Pass or you can even customise it to your own preferences. If you’ll be spending 2 days in Boston then you surely just need to tick off the places that you surely will be heading out to.

We can’t reiterate how helpful a Boston Go Card is, so you surely need to purchase one for your trip to Boston!

Where to Stay in Boston?

Travelling solo:

If you’re a young solo traveller, then you surely will want to stay at a hostel. HI Boston Hostel is our top pick for its location, price points and its vibe. If you’re looking to meet new friends to go on adventures with, then this spot is the perfect place for you!

Group travel:

If you’re going as part of a bigger group and if you’ll be heading to Boston with your families, then a hostel might not be the best idea.

Boston is also filled with top hotels but if you’re wanting for a more specific experience, then might we suggest staying at FOUND Hotel Boston Common? This is a great boutique hotel that is located in the heart of Boston. FOUND is perfect due to its location, the vibe and the facilities make it perfect for groups!

2 Days in Boston – Day 1

Breakfast at The Thinking Cup

Breakfast at The Thinking Cup, 2 Days in Boston, weekend in Boston itinerary

The Thinking Cup

We stumbled upon this perfect coffee shop whilst trying to find a breakfast spot. The Thinking Cup coffee shop is the most fantastic go-to place for when you’re craving for that simple American breakfast and for that strong cup of your morning coffee.

There are only 3 locations in the world but the one we found was right next to the start of the Freedom Trail. This makes it the perfect place for a spot of breakfast before heading off on your day filled with historical adventures!

Breakfast at The Thinking Cup, 2 Days in Boston, weekend in Boston itinerary

Breakfast at The Thinking Cup

We loved The Thinking Cup so much that we decided to eat here for 2 days straight. The coffee and food are delicious and a terrific spot to start your 2-day Boston weekend itinerary.

Boston Public Gardens

Boston Public Gardens, 2 Days in Boston, weekend in Boston itinerary

Boston Public Gardens

Located right next to the start of the Freedom Trail, the Boston Public Gardens are not to be missed before your journey on the Freedom Trail.

Boston Public Gardens, 2 Days in Boston, weekend in Boston itinerary

The Boston Public Garden was established in 1837, and this was the first botanical garden in the United States. The garden maintains a Victorian elegance and has had swan boats for rent for over 100 years!

Start The Freedom Trail

Boston Freedom Trail, 2 Days in Boston, weekend in Boston itinerary

The Freedom Trail is one of the many trails located around Boston, and dare we say that this is the ultimate highlight of Boston. At 2.5 miles long, the trail shows the best parts of Boston and so much more! If you’re planning to spend no more than a day in Boston, then this trail is a must.

This particular trail is filled with historical parks, churches, museums, burying grounds, a ship, historical houses, and so much more! You can experience the trail in several ways such as hiring a tour guide, doing a DIY self-walking tour, or even an audio tour.

I suggest taking all day to complete this trail because it’s really filled with so many great sites and history.

The Freedom Trail begins at the Boston Common and this place is known as the oldest public park in the United States. The Commons was my favourite park in Boston due to the shapely trees, the modern skyscrapers in the distance, and the colourful flowers.

The Massachusetts State House, 2 Days in Boston, weekend in Boston itinerary

The Massachusetts State House

After the Boston Common, the trail takes you through The Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel, King’s Chapel Burying Ground, Benjamin Franklin Statue & Boston Latin School, Old Corner Book Store, Old South Meeting House, Old State House, and the Site of The Boston Massacre.

Old State House, 2 Days in Boston, weekend in Boston itinerary

Old State House

At some of the sites, you can tour inside but it costs $10-$20 per person.

Granary Burying Ground where Benjamin Franklin’s parents were buried, 2 Days in Boston, weekend in Boston itinerary

Granary Burying Ground where Benjamin Franklin’s parents were buried

Eat: Lunch at Quincy Market or Faneuil Hall Marketplace

Faneuil Hall Marketplace, Quincy Market, 2 Days in Boston, weekend in Boston itinerary

Quincy Market or Faneuil Hall Marketplace

The Quincy Market is located on the freedom trail between the site of the Boston Massacre and Paul Revere’s house. The proper name of this area is actually called “Faneuil Hall Marketplace”, a name that the Boston Mayor Josiah Quincy requested.

But eventually, a sign “Quincy Market” was added to commemorate the mayor who helped create the market.

Quincy Market comprises 3 main buildings: Quincy Market, North Market, and South Market. Each place is filled with restaurants, stores for shopping and food stalls. This area is usually quite buzzing on weekends due to tourists and locals trying to enjoy the day.

We can’t reiterate how the Quincy Market is a place that you really must go to because it simply is historic and beautiful!

Pepper Palace in South Market, 2 Days in Boston, weekend in Boston itinerary

Pepper Palace in South Market

Tip: Make sure to visit the Pepper Palace in South Market if you love hot sauces like us. 

Finish The Freedom Trail

Old North Church, 2 Days in Boston, weekend in Boston itinerary

Old North Church

After taking our lunch at the Quincy Hall, we set out to finish the Freedom Trail at the Paul Revere House, Old North Church, Copp’s Hill Burying Ground, the USS Constitution, and Bunker Hill Monument.

Copp’s Hill Burying Ground, 2 Days in Boston, weekend in Boston itinerary

Copp’s Hill Burying Ground

The last set of destinations only had a few sites in close proximity but there was still quite a few people walking around. These spots were a bit hidden, but it still was as beautiful as the others. Plus, it can be considered as off-the-beaten path places.

USS Constitution, 2 Days in Boston, weekend in Boston itinerary

USS Constitution

When we visited, the largest crowd of people were trying to see the USS Constitution as the ship was surreal to see. You’re able to see several decks of the ship and see how the sailors lived. This is a really fun activity if you’re into sailing and marine life!

Eat: Dinner at North End – Mamma Maria or Lucca

North End, Mamma Maria, 2 Days in Boston, weekend in Boston itinerary

Mamma Maria at North End,

One of my favourite spots of Boston was the North End. Why?

Because the area has loads and loads of Italian restaurants… and who doesn’t love Italian food?

We were lucky enough to grab a spot at the famous Lucca restaurant at the last minute and it was spectacular.

Mama Maria is also a well-known Italian restaurant in the city. If you’re into Italian food, then these are the places you should be eating at!

Things to do in Boston this weekend – Day 2

Visit the Commonwealth Avenue Mall, Back Bay

Commonwealth Avenue Mall Park, Back Bay, 2 Days in Boston, weekend in Boston itinerary

Commonwealth Avenue Mall Park

Established in 1856, Back Bay was a bay that would flood due to the Atlantic Ocean sending in waves to the Charles River. Eventually, a dam was built along with a new park called Commonwealth Avenue Mall.

The park is about 52 acres and is known for the beautiful uniformed trees. This particular park is a great place to take a morning stroll in and to just take in all the greenery along with the surrounding Bostonian architecture.

If you’re spending no more than 2 days in Boston, then you surely need to allocate a morning for this spot because it simply is breathtaking!

Walk to the Charles River Esplanade, Back Bay

Commonwealth Avenue Mall, Back Bay, 2 Days in Boston, weekend in Boston itinerary

Charles River Esplanade

The Esplanade Park runs about 3 miles on the shore of Boston, and it’s adjacent to the Charles River. The park has plenty of views of the river, the city, and its several bridges. Many locals simply enjoy the scenery here but this park is also great for running, kayaking, or even just taking a casual stroll. The park is the perfect spot to hang out and enjoy the day.

The Esplanade is also a great seasonal area to experience.

During spring, the days are filled with colourful and bright cherry trees bursting into bloom.

The summer days bring in the sun and this is when people usually love to lounge around on the 5 floating docks and listen to music under the stars at The Hatch Shell.

Of course, fall brings in bright orange and yellow foliage.

The park is the best spot to witness the colourful changes in the seasons, so there surely is a treat for you no matter what season you visit!

Visit Copley Square, Trinity Church and the Boston Public Gardens, Back Bay

Trinity Church, 2 Days in Boston, weekend in Boston itinerary

Trinity Church

The Trinity Church and the Boston Public Library are located right next to each other and both places are very interesting historical markers.

The old historical buildings with the modern tall skyscrapers in the backdrop make for the best pictures. If you’re an Instagram fanatic then you surely can’t miss taking a gorgeous photo in this spot!

Copley Square is an energetic area full of life and sunshine; all you need to do is take a seat on one of the benches to take in the beautiful crisp air. Sometimes there can be beauty in appreciating the stillness of things.

Boston Public Library, 2 Days in Boston, weekend in Boston itinerary

Inside the Boston Public Library

Personally, my favourite part was the inside of the library because the architecture inside was simply stunning and the library was filled with countless works of art.

The library also holds about 29 million items such as things like books, CDs and what-not. This is actually the second largest public library in the United States. This library rivals with the likes of New York’s famous public libraries, so stopping by here is a must!

Eat & Shop: Newbury Street or Boylston Street, Back Bay

Newbury Street, Boylston Street, 2 Days in Boston, weekend in Boston itinerary

Shopping on Newbury Street and Boylston Street

Newbury Street and Boylston Street in Boston are lined with with a bunch of trendy shops. It’s a perfect destination for tourists and locals alike.

After making sure that your shopping is complete, make sure to grab some lunch at some chic spots. Some recommendations are Atlantic Fish Company, Back Bay Social, Mcgreevy’s, L’espalier, and Parish Cafe which is where we ended up eating at.

Sam Adams Brewery Tour

Sam Adams Brewery Tour, 2 Days in Boston, weekend in Boston itinerary

One of my favourite beers of all time is the Sam Adams seasonal beers. I mean, who doesn’t love seasonal beers by Sam Adams? It’s a classic American staple and they do have some delicious flavours!

When I originally found out we were going to spend a weekend in Boston, I made sure to pencil in the Sam Adams Brewery Tour. Believe me when I tell you that this spot is a must!

The brewery is located on the southwest side of town and the ride to this brewery was a bit longer than I expected…but it was totally worth it!

Sam Adams Brewery Tour, 2 Days in Boston, weekend in Boston itinerary

Sam Adams Brewery Tour

The classical tours are on a first-come-first-served basis and they’re free of charge. The tours run about every thirty minutes. During the tour, you’ll learn about the brewing process and the different types of ingredients they use to make their famous beers.

The best part of the whole tour is at the end when you can finally have the opportunity to taste the different beers whilst they give you some background on the process and on the ingredients.

In the end, you get to keep the tasting cup and the buzz from the tasting!

Bear in mind that looking at the schedule before heading out is crucial. The brewery is a little far and the tours are only open during certain hours of the day, so really check out the schedules or else you might go all the way there for nothing…yikes!

Eat: Dinner at Union Oyster House or Emmets Irish Pub

Union Oyster House, 2 Days in Boston, weekend in Boston itinerary

Union Oyster House

If you’re a fan of oysters, lobster or just seafood in general, then you simply HAVE to stop at Union Oyster House. This restaurant is located on the Freedom Trail and it’s the oldest restaurant in the whole United States! They opened their doors in 1826 and have since been established as a National Historical Landmark.

The oysters were very fresh and savoury whilst the lobster was superb. If you’re a history buff, experiencing the first ever restaurant in the USA is a must.

When I first started researching for this 2-day Boston itinerary, I asked a local Bostonian to recommend some spots.

Emmets, irish, ireland, beer, 2 Days in Boston, weekend in Boston itinerary


One of the restaurants or pubs she recommended to me was Emmets. I lived in Texas and there was no such thing as a real Irish pub…so I was sold on the idea right away!

Holy cow was she right!

The beers were cold and plentiful whilst the food was delicious. We had never tried Irish food before and we were pleasantly surprised. We ordered ‘The Taste of Ireland’ and it was a perfect combination of their 3 most popular meals. The dish was savoury to say the least.

What to Eat in Boston

New England is famous for its seafood, and Boston is no exception to the rule.

If you’re looking for a great yet affordable restaurant to eat seafood in, why not head out to Neptune Oyster or Yankee Lobster? These are two of the best spots to eat in all of Boston…plus, a local recommended these places so it must be worth a try.

Grab a beautiful piece of lobster roll from either of these places and just sit by the dock. Boston is a beautiful city and its water landscapes should be admired. What better way to appreciate what this city has to offer than by hanging out by its waters and eating its local food, right?

What to Do in Boston at Night

Boston is a fun and vibrant city and you’ll never want to miss a night out in town.

Some of the best places to head over to if you’re up to try out some drinks are 21st Amendment, Wild Rover, The Hawthorne, Ward 8 and so much more!

If you’re not up for a quick drink, then you can simply walk around the city and just take it all in. Boston is a beautiful city no matter if you drink a bit or if you’re completely sober. This city will welcome you with open arms and it will make you see its beauty no matter what.

Boston is the perfect weekend summer getaway…although it’s a city that will welcome you in every season. It’s filled with history, culture and beautiful architecture. The fantastic vibe is simply a plus!

Honestly, you might be surprised by how much you’ll fall in love with this city. Boston surely took me by surprise. The best thing is, it can easily be covered in no more than 2 days!

Make sure to visit Boston, at least, once in your life because this city will surely take you by storm. It’s equally as beautiful as it’s historic, and there’s just so many things to do. Fall in love with Boston just like we did; you surely will not regret your visit here!

Has any city ever surprised you, like Boston surprised me?

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Michelle Stelly lives in Dallas, Texas and is a full-time engineer. In her spare time, she loves to travel and her favourite destinations are National Parks. She blogs about her experiences and provides suggestions through her blog, The Wandering Queen. Michelle takes on her adventures with her husband Jameson and together, they travel the world, continually improving their photography skills. Follow Michelle Stelly to find out how a full-time professional can turn life into a fun adventure.
Isabel Leong

Isabel Leong

Full-time travel blogger at Bel Around The World and SEO coach roaming the world at a whim, Isabel helps aspiring content creators and brands get the most out of their online presence by attracting organic leads/traffic and achieving financial freedom with her Skyrocket With SEO course. She's closely involved in and has been featured as a speaker in other travel & digital nomad networks & podcasts such as Traverse, Travel Massive, The Nomadic Network and Location Indie.

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