2 Days in Boston Itinerary: The Perfect Boston Weekend Getaway!

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If you’re looking for an epic 2 days in Boston itinerary, you’ve come to the right place!

I freaking LOVED my time in Boston and, after almost a week spent sightseeing, eating and drinking there, I’m pretty confident that I’ve pulled together the best Boston weekend itinerary on the web (*hair toss*).

The city of Boston is surprisingly easy to travel around since it’s one of the few cities in the US with a comprehensive public transport system!

Pair that with its many captivating historical attractions, the mouth-watering Italian food and, of course, the fun accent (we love a fun accent!) and you’ve got the perfect recipe for an epic Boston weekend trip.

Planning a short trip to Boston can feel overwhelming, though. There are just so many things to do there! If it’s your first time in Boston it’ll feel even trickier.

Fear not – in this post, I’m going to cover all of the must-see attractions in the city as well as my tried-and-tested food recommendations. So, whether it’s your first time in Boston or your fifth, you’ll still find some solid recommendations in this itinerary.

Let’s get started!

How Many Days Should I Spend in Boston?

Two days in Boston is the perfect amount of time to see Boston’s top sights, eat some incredible Bostonian food and get a flavour of the city.

It’s still possible to spend just one day in Boston, but you’ll have a very full day and will have to be very selective about what you add to your itinerary! For one day visits to Boston, I recommend sticking to the Freedom Trail walking tour.

For numerous reasons that I’ll go into down below, I actually ended up staying for almost a week in Boston! In my experience, this was a bit too long. However, if you’re able to extend your 2 days in Boston to 3 or 4 days you’ll get the chance to explore the city’s wonderful surroundings, such as Salem, Cambridge and Harvard, and Cape Cod!

So, in my opinion 2 days in Boston is the right amount of time to spend in the city itself. If you want to see any of the other nearby destinations you’ll need another day or two.

2 Days in Boston Itinerary: Step-by-Step

Here’s what to see in Boston in 2 days!

Day 1: The Freedom Trail and the North End

Stop 1: Boston Duck Tour

You’ll get the perfect introduction to Boston on the city’s famous duck tour! This 80-minute guided tour takes you past all of the city’s highlights and gives you a whistle-stop tour of the city’s history and unique identity.

What makes the Boston duck tour so unique is that once on board you’ll get to check out the city from land and water. Yup! The duck tour takes place on a WW2-style amphibious vehicle, meaning you’ll get to whizz past all of the city’s most famous landmarks and cruise along the Charles River without moving from your seat!

Click here to book your seats in advance – this tour often sells out!

Stop 2: Walk the Charles River Esplanade

After an action-packed 80 minutes you’ll get dropped off near the Charles River Esplanade, so there’s no better way to unwind and check out one of Boston’s most scenic areas than by taking a riverside stroll. 

The esplanade stretches for three miles along the river, but obviously you don’t need to walk all of that!

Instead, I recommend just taking in a small chunk of it as you walk from the Duck Tour drop-off area towards Boston Common, the oldest public park in the United States.

Stop 3: Boston Public Gardens & Boston Common

Next up on this 2 day Boston itinerary is Boston Common, Boston’s version of New York’s Central Park.

You’ll get some beautiful views of the city’s skyline from here, and there are also plenty of fascinating places to visit inside the park.

Start in Boston Public Garden, where you’ll find the George Washington statue and a stunning suspension bridge over a lake where you won’t be able to resist taking photos. Heading over to the corner of the Boston Public Garden, you’ll find the adorable “Make Way for Ducklings” sculpture.

Locals often decorate the ducklings in custom-knitted outfits or hats, and children frequently sit on the back of the mother duckling for cute photos. It’s one of the most adorable sculptures you’ll ever see!

Walking over to Boston Common you’ll find plenty of different temporary attractions depending on the time of year you visit. I visited Boston over Memorial Day weekend so a huge part of the common was covered in American flags fluttering in the breeze, which was quite touching.

Stop 4: Lunch at Cafe 26

Fancy having breakfast for lunch? Great, because the popular Cafe 26 serves up exactly that.

This was the first place I ever tried banana pancakes, and wow they were worth the wait! The menu here is pretty huge, covering all of the classics, and the prices are reasonable. 

Stop 5: USS Constitution and USS Cassin Young

In the afternoon of your first day in Boston, I recommend heading over to the final few stops of the Freedom Trail. There’s a method to my madness here, I promise. The Freedom Trail has a lot of stops, and in my experience if you’re going to dedicate enough attention to each stop you can’t really do it in a day without being flat-out exhausted!

The parts of the Freedom Trail that are on the first day of this Boston itinerary are quite a walk away from all of the others, so it actually makes a lot of sense to split them up in this way.

USS Constitution

This famous ship from the War of Independence is still in the harbour over in Charlestown, and you’re able to board it and explore! Since it is located in Boston National Historic Park you’ll need a photo ID to enter. Luckily, though, admission is free!

As well as being famous for its exploits during the War of Independence, the USS Constitution is the US Navy’s oldest commissioned ship. It was built way back in 1797.

Wandering the decks and descending into the depths of the ship you’ll learn all about what life was like on board this ship for the crew who worked here, and you’ll be surprised by just how cramped it must have felt on board!

There’s not a whole lot of information on board, which makes it perfect for just roaming around, but if you’re looking for more history, check out the USS Constitution Museum next door.

USS Cassin Young

Just a short walk away and also inside the Boston National Historic Park (meaning entry to this ship is also free!) you’ll find the much more recent USS Cassin Young, which was built in 1943.

This ship engaged in seven Pacific battles during WW2, survived two Kamikaze hits, and continued serving a whopping ten years past its expected retirement date!

You’ll only need 15 minutes here, making it an easy stop to squeeze into this whirlwind Boston 2 day itinerary, but if you’re at all interested in modern history it’s worth a quick walk around.

Stop 6: Bunker Hill Monument

Next up is the Bunker Hill Monument, the 221-foot stone monument which commemorates the Battle of Bunker Hill, which took place right here!

The Battle of Bunker Hill was one of the first major battles of the American Revolution. Although the park around the monument is a lovely place to hang out for a while, the reason we’re truly here is to climb to the top.

Yup, I hope you’ve brought good walking shoes because there are 294 steps to the top! It goes without saying that from the top you’ll get epic views over Boston. What’s more, admission is free!

Stop 7: Drinks at Warren Tavern

It’s time to reward yourself after such a strenuous climb, and where better than the oldest tavern in Massachusetts? 

You’d think this impressive history would mean that it’s become a bit of a tourist trap, but I’m happy to confirm that isn’t the case! The service here is great, the food is delicious (so if you’re peckish I can recommend their pretzels and sweet potato fries), and it has a lovely outdoor area where you can chill out in the sun.

The Warren Tavern has seen countless famous visitors over the years, including both George Washington and Paul Revere. If it was good enough for them, it’s good enough for me!

Stop 8: Boston’s North End 

It’s time to wrap up your first day in Boston in the North End, the city’s Italian quarter. It goes without saying that the food here is out of this world, and you really can’t go wrong!

If you’re visiting Boston for the weekend I highly recommend researching where you want to eat dinner and booking a table in advance. This is the hottest place in town for dinner, so you don’t want to miss out!

Mike’s Pastry and Modern Pastry

Start your visit in the North End at either Mike’s Pastry or Modern Pastry to sample their famous cannoli. Or even better – try them both!

There are some very strong opinions out there on whether Mike’s or Modern is best, but only you can decide for yourself. I personally preferred Mike’s, but I’d love to hear which one is your favourite!

Cannoli at both places costs $5. Mike’s is where you head for exciting fillings and fun toppings, and Modern is where you head for authentic Italian cannoli. 

Caffè dello Sport

If you fancy checking out whatever sport is on at the moment, from basketball to European soccer, head to Caffè dello Sport. This community-feel cafe is the perfect place to grab a drink and catch the game in Boston.

Service is a little slow but it’s quite affordable and their Espresso Martinis are next level!

Carmelina’s

We dined at Carmelina’s and the food here was sooo tasty! I ordered the mushroom pasta and Rob ordered the gorgonzola pasta, and our first taste of American-Italian food did not disappoint!

Day 2: The Red Sox and Paul Revere

Stop 1: Breakfast at Tatte Bakery

Tatte is a Boston institution, and their baked goods take things to the next level! This Israeli-French coffee shop and bakery is awash with Instagram influencers thanks to its gorgeous decor and photo-worthy treats.

Even if you’re not an Instagrammer, though, it’s worth stopping here for breakfast. The food here tastes just as good as it looks!

Stop 2: Fenway Park

Even if you’re not into baseball you’ve probably heard of Fenway Park, home of the Red Sox since 1912. Obviously the best way to see Fenway is at a Red Sox baseball game, but if there aren’t any fixtures during your time in Boston you have another option – to take a tour of Fenway Park.

This 1-hour guided Fenway Park tour will take you to all of the Park’s highlights such as the 37-foot tall “Green Monster” and the Red Sox Roof Deck, as well as the Fenway Park Living Museum where you can see some of the most famous Red Sox memorabilia in existence! 

Your guide will be able to answer any questions you have about Fenway Park and the Red Sox and will take you to all of the hotspots of the stadium.

Stop 3: Massachusetts State House

With Fenway Park ticked off your list, it’s time to complete the Freedom Trail by visiting the sites you didn’t get around to on day one of this Boston itinerary. Let’s start with the gold-domed Massachusetts State House, the state capitol. 

You can apparently go inside the building on free guided tours, but we decided to just check it out from the outside so I’m not sure how good the tours are.

The Massachusetts State House is in Beacon Hill, a beautiful neighbourhood. If you have time, it’s worth heading over to the historic and photogenic Acorn Street before carrying on.

Stop 4: Granary Burying Ground

A short walk around the corner is the Granary Burying Ground, which is the resting place of some of Boston’s most important historical figures and revolutionaries. In the cemetery, which was founded in 1660, you’ll find the graves of Paul Revere and Samuel Adams, to name just a few.

At the entrance to the cemetery there’s a guy handing out laminated guidebooks he created himself. You can borrow one for free, and I highly recommend picking one up. The guidebook will point out the most important graves, share a tonne of local history relevant to the graveyard, and point out a few lesser-known graves that are also interesting. 

There’s a wallet in the back of the guidebook where you can leave a tip if you wish before handing the book back as you leave.

Stop 5: Old South Meeting House and Old State House

Following the Freedom Trail, you’ll come across two of the most important buildings in Boston’s history – the Old South Meeting House and the Old State House.

Old South Meeting House

The Old South Meeting House was built in 1729 and was actually the place where the Boston Tea Party began. This is because it was the venue often used for big public debates about British rule as it was the largest public gathering place in Boston.

It was also outside this building that the protests over the Boston Massacre of 1770 took place. 

It’s totally fine to just check out this building from the outside (which is what I chose to do), but if you want to enter you’ll need to purchase the combined ticket. This ticket, which costs $15, will get you entry to both the Old South Meeting House and the Old State House.

The Old State House 

The Old State House was built just before the Old South Meeting House, in 1713. It’s the oldest surviving public building in Boston and the front of the building was the 1770 Boston Massacre site.

It was also underneath the balcony of the Old State House that people gathered to hear the Declaration of Independence read out for the first time in 1776.

Afterwards, if you have time, head over to Faneuil Hall marketplace for a bit of shopping.

Stop 6: Lunch at Quincy Market

The historic Quincy Market is a must-visit in Boston if you want to sample some famous Boston cuisine. From clam chowder to lobster rolls, huge slices of Boston pizza to candy, this market has it all!

I can personally vouch for the hot butter lobster rolls at the Boston & Maine Fish Company (SO good!) and the pizza slices at Regina Pizza (the slices here are out of this world).

Stop 7: Paul Revere House

One of the most famous landmarks in Boston, and the top attraction on the Freedom Trail, is the Paul Revere House.

Whether you learnt all about Paul Revere in school or know absolutely nothing about him (and I was certainly in the latter category before my visit), the Paul Revere House is a fascinating place to visit where you’ll certainly learn a thing or two.

This black house was built around 1680 and was owned by Revolutionary figure Paul Revere from 1770 to 1800. He was living here when he embarked on his legendary “midnight ride” – and no worries if you have no idea what this is. You’ll find out all about it on your visit!

The Paul Revere House is open daily and tickets cost $6 for adults. Top tip: if you’re travelling alone you’ll need to pay in cash as they have a $10 card minimum here.

Stop 8: Old North Church

Just a short walk through the North End will lead you to Boston’s oldest church, the Old North Church. It was established in 1723.

It costs $5 to enter, so I just decided to admire it from the outside. I’m from Europe, after all, so I’ve seen my fair share of old churches!

Aside from being so old, what makes the Old North Church so special? Well, it was from here that the infamous “one if by land, two if by sea” signal is thought to have been sent.

This was an early warning sign that the British Army was crossing the Charles River and heading towards Lexington and Concord on the night of Paul Revere’s Midnight Ride.

Stop 9: Drink at Green Dragon Tavern 

After such a jam-packed day of sightseeing, it’s time to reward yourself with a drink. There’s no better option than the historic Green Dragon Tavern.

The tavern was established in 1634 and played a key role in the War of Independence. It was apparently one of the favourite pubs of Paul Revere and John Hancock!

The decor on the outside and inside is so old and quaint, it felt like one of the old pubs at home in the UK rather than one in America! There’s a good range of beers local to New England here but you really can’t go wrong with Harpoon IPA.

Stop 10: Dinner at Rino’s Place

From the Green Dragon Tavern you’ll need to catch the T Blue Line from State to Airport station. The incredible Rino’s Place is just a short walk away and is absolutely worth the trip out to East Boston.

This family-run Italian restaurant has been featured on Diners, Drive-Ins and Dives. It also serves the BEST PASTA I HAVE EVER EATEN! Honestly, you guys, I would go back to Boston just to eat here again.

You can’t make reservations so if you’re visiting on a Friday or Saturday night you’ll have to wait for a table. If you get there early, though, you’ll probably walk right in. 

I ordered the lobster ravioli, which, at around $40, definitely wasn’t cheap, but there was so much lobster stuffed into that ravioli that it probably should have been priced higher!

Rob ordered the matriciana, which I think was around $20, so much more affordable, but still mouth-wateringly good. The portion sizes here are insane so you’ll have to take your leftovers to go.

Extra Travel Information For Your 2 Days in Boston

Boston Travel Tips

With 2 days in Boston you’ll have plenty of time to check out the city’s most famous attractions, sample some drool-worthy Boston food and leave you planning your next trip to return here!

I actually ended up staying in Boston for a whopping six days because I wanted to go at a leisurely pace (and see pretty much everything), explore the nearby areas, and catch the Paul McCartney concert at Fenway Park. It was one of the best things I have ever done!

Anyway, enough about me. If you’re looking for travel tips for your 2 days in Boston, here’s everything you’ll need to know.

Extending Your Weekend Trip to Boston

Got more time and fancy a long weekend in Boston? Great! Check out the Isabella Stewart Gardner Museum for awesome art, the site of the Old Corner Bookstore (which is now a Chipotle, lol), the Boston Public Library, or Park Street Church.

If you’re spending 3 days in Boston as a family, the New England Aquarium is the perfect place to visit on that third day.

If you’d prefer to get out of the city, there are also tonnes of brilliant day trips from Boston without a car that you can go on to explore some of the city’s surroundings. 

The easiest is probably Cambridge, where you can explore the famous Harvard and MIT universities. Another great option is Salem, Massachusetts. My Salem day trip guide will help you to figured this all out!

Fancy a trip to the coast? It’s possible to take the ferry from Boston to Provincetown, Cape Cod for a day trip, or head out on the train to Portland, Maine, amongst other great day trips!

If you do have the time, I highly recommend adding a day or two to your 2 days in Boston to give yourself some time to head out on a day trip or two.

Airport and Transportation Tips

The easiest way to get to Boston is to fly. Boston has one airport, Boston Logan International Airport (BOS), and it’s pretty easy to get to the city from the airport. The easiest way is to catch an Uber, which will cost around $25 plus tip to downtown. 

However, you’re also able to catch the Blue Line of the T (Subway). There’s a free shuttle bus from each airport terminal that will take you to the Airport subway station, and from here you can get downtown in around 30 minutes, which will cost you $2.40.

You really don’t need to hire a car in Boston. It’s one of the best cities in the US when it comes to its public transport system! The main method of transportation you’ll use will be the T (what Bostonians call the subway).

The T has numerous lines all across the city and one-way tickets cost $2.40. 

If you’re staying for two days or more in Boston and need to take the T from your hotel to downtown I recommend purchasing the 7-day pass for $22.50. It works out as better value if you’re going to be taking the subway a lot.

What is the Best Time to Visit Boston?

I recommend visiting Boston in the shoulder season months of May, June, September, and October. Winters in Boston can be brutal, with short daylight hours. It’s best to avoid them if possible. Summers can also be baking hot in the city, which isn’t ideal for sightseeing.

It’s good to prepare for all types of weather during your 2 days in Boston. During my trip in early June I experienced torrential rain, extreme sun and heat, crazy humidity and one extremely windy day that was quite cold. Pack for all eventualities!

Where to Stay in Boston

Boston is expensive to visit, there’s no doubt. If you’re looking for a deal it’s better to visit Boston in winter, when hotel prices literally plummet. Weekdays are also, obviously, cheaper.

I’ve seen a hotel room on a summer weekend go for $500 when for a weekday in January it would cost just $150 – the price fluctuation is absolutely wild. If you’re visiting Boston on a weekend getaway, you’ve been warned! Book in advance!!!

It’s worth double-checking that there are no big events taking place in Boston for your dates before looking for hotels. 

We accidentally ended up in Boston on a night where both Paul McCartney played Fenway and the Celtics played in the NBA final at the TD Garden and… *shudders*… our accommodation for that night cost us SO. MUCH. MONEY.

Anyway, with that warning out of the way let’s get into some accommodation recommendations for your 2 days in Boston!

Hostel

If you’re travelling to Boston on a budget, and especially if you’re travelling solo, this hostel is the best place to stay in Boston. Located near Boston Common, you can’t find a more central location! Breakfast is also included, which will help you to visit Boston on a budget.

Since this is the only decent hostel in Boston it gets booked up fast. I recommend booking as far in advance as you can. A dorm bed will set you back around $60, so it’s certainly not cheap, but it’s by far the cheapest you’ll find in Boston!

Click here to check availability & book!

Budget Hotel

You guys, finding anywhere half-decent to stay in Boston on a budget is a mission, let me tell you. After putting my budget travel ninja skills to the test, the best I could find was this budget hotel, where we stayed for four nights.

You’ll have to catch the T for a couple of stops to get into the centre (the journey takes around 15 minutes), but it’s worth it for the money you’ll save. 

We paid $160 a night but split between the two of us it was $80 each, so not too bad. This is not the most incredible hotel you’ll ever visit but it’s clean, spacious, fairly affordable and it’s close to the T station. You don’t really need much more!

Click here to check availability & latest prices!

For the rest of my trip I stayed in this “budget” hotel, but I don’t have anything good to say about it aside from its location right next to the TD Garden. The rooms are tiny, it’s SO overpriced, and the staff sucked. 

Mid-Range Hotel

If you’re travelling to Boston on a mid-range budget your options open up when it comes to good-quality hotels in Boston! 

Word of warning for my European readers, though – a mid-range budget in the US typically costs more than double what you’d pay in Europe! Hotels in US cities are just expensive.

Situated just a 3-minute walk away from Boston Common, this boutique hotel is perfect if you’re looking to get something special from your fun weekend in Boston. You’ll feel super fancy entering its onsite cocktail bar, and you’ll love the sweeping views of the city from your hotel room window.

Click here to check availability & latest prices!

I absolutely adored my time in Boston and I’m certain that, by following this 2 days in Boston itinerary, you’ll have the time of your life here too!

I’d return to Boston in a heartbeat, even after I spent six days there!

I’ve tried to cram as much as possible into this Boston trip, but the more time you spend in the city the more you’ll get to see. There are just so many things to do in Boston!

If you’re waiting for a sign to visit Boston this is it. Go! You can thank me later 🙂

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