I’m soaking wet despite my weatherproof jacket and shoddy umbrella. I nurse my pizza box into my chest. Through squinty eyes, I watch a mini puddle form on top of the gigantic box as I hurriedly walk back to my apartment. The rain this day in Boston beats down like an open fire hydrant pointing downwards. The box is resilient enough to hold up against the elements and most importantly, keeps my pizza dry. That inclement weather robbed us of a day. But not before we’d already had 2 days in Boston with magical fall weather.
Trees half filled with dead leaves. Green grass with a blanket of all the colours of autumn. There are yellows and orange leaves for sure, but my favourite are the rich red leaves set against a clear blue sky. You get every color imaginable in Boston in the fall. It has to be one of the prettiest places to visit during this season.
No matter the season you visit, Boston is a city that offers more than pretty colors. The city that has educated some of the most brilliant minds in the western world. An enviable sporting pedigree. And of course, the home of the United States as we know it.
Boston is a city that you can easily while away a week or longer if you desired it. If time is of the essence, 2 days in Boston will absolutely do the trick (hello weekend break!). Read on find out how to maximise your 2 days in Boston.
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2 days in Boston
At a glance
Day 1 || Explore some of Boston’s stunning gardens || Take in Boston on foot on the famous Freedom Trail || Dine in Little Italy
Day 2 || Step into the inside of the Earth at the Mapparium || Go inside Boston’s rich sporting history || Walk in the footsteps of Harvard alumni
Day 1 morning
Welcome to Boston! Start your 2 days in Boston Public Library. This library dates back to 1848. With some 23 million items in its keeping, if you need to find something, there’s a fair chance you’ll find it here. Whilst its size is impressive, the real gem here is the McKim Reading room. Dotted with classic green lamps underneath a spectacular curved and detailed roof, it’s one of the most stunning locations you could find to study.
Boston Public Library address: 700 Boylston St, Boston, MA 02116, United States
Head out of the library and towards the Boston Public Garden underneath the tree lined Commonwealth Avenue. You can spend as little or as long here as you like taking in its various fountains, lagoon and even take a boat ride. The George Washington Statue here is one of the most photographed statues in Boston, so be sure not to miss it.
Cheers fans can make a slight detour north out of the garden and across Beacon Street where you can visit the original Cheers bar.
Wandering up Beacon Street towards Charles Street, the green space in front of you is the famed Boston Common. American’s oldest park, it is filled with stunning open spaces and various monuments not dissimilar to the Boston Public Garden. In winter, you can even enjoy ice-skating on the Boston Common Frog Pond.
Boston Common is also where you’ll start what was an enormous highlight of our trip, the well known Freedom Trail. The Freedom Trail is a 2.5 mile path, taking in some of most significant national monuments of not just Boston, but the United States. There are 16 stops in all, all marked with a red brick path which will have you zig-zagging your way through the sights.
Start the freedom trail
Start your trail at the Freedom Trail monument located just inside the Common across from the Tremont Street and West Street intersection. If Google Maps and the red brick path isn’t enough, duck into the Visitor Information building here and pick up a map. The map will provide further details about each site as well.
Note: If you’d prefer to the Freedom Trail with a guide, there are of course options for that too.
Strolling through the Common, your second stop will be the Massachusetts State House. The home of the Massachusetts government since 1798 you can’t miss the stunning gold coloured roof which shines like a beacon on a sunny day.
Park Street Church will be your next stop, followed by the Granary Burying Yard. In the fall, this is a stunning location with its many off-kilter head stones underneath a canopy of red, yellow and orange. Here, you’ll find some notable Americans including Paul Revere, Samuel Adams and John Hancock laid to rest here.
King’s Chapel and its Burying Ground are next, followed by the Benjamin Franklin statue at the site of former Boston Latin School. The bronze statue here of Franklin is a popular photo opportunity.
A slightly different historical detour as you then head to the Old Corner bookstore. Or, if you’re putting on your best Bostonian accent, the Old Connah bookstore. Home to a publishing company in the mid 1800s, authors of note who frequented this bookstore included Charles Dickens, Henry Wadsworth Longfellow and Ralph Waldo Emerson.
The Old South Meeting House where the Boston Tea Party was planned is next up, followed by the Old State House. The State House is one of the oldest public buildings in the United States. It is most famous as the site of the first ever reading of the Declaration of Independence. I’m not sure you can pack more US history into 2 sites!
Outside of the Old State House, you’ll find the site of the Boston Massacre. You’ll no doubt find actors and guides outside willing to tell you more about the site that resulted in the British Army firing on a crowd of Bostonians. Five people lost their life, and it this event was one of the catalysts for the American Revolution.
Day 1 lunch
Faneuil Hall
Let’s get the awkwardness out of the way. There are two commonly accepted pronunciations for Faneuil Hall. Fan-youll or fannel. People feel strongly about their preferred pronunciation, but you’ll be laughed at less if you stick with one of these two versions.
Faneuil Hall is one of the oldest marketplaces in the US. With a range of shops, the real highlight for us was the selection of food available at Quincy Market. Here, you’ll be able to sample some of the very best Boston has to offer. You can try some traditional Boston pizza at Regina Pizzeria. Or go for something very Massachusetts and eat a lobster roll and chowder at the Boston Chowda Company.
If you’re with a partner or amongst friends, it’s a great place to sample a range of different foods. Go nuts and fill up before continuing to trail in the afternoon.
Day 1 afternoon
With a full stomach, the next destination you can enjoy slowly. It’s the home of Paul Revere. See the home of the man who coined the phrase “The Red Coats are coming”. Forever remembered as a hero, his home was quite impressive for the time.
Your next stop is another Revere inspired spot. The Old North Church is the site where Paul Revere hung two lanterns to warn the people of Boston that the British were coming.
Copp’s Hill Burying Ground is next up. By this stage you may be a little ‘churched and graveyard-ed’ out. Nonetheless, it’s a beautiful graveyard which deserves a quick wander.
Heading across the North Washington Street Bridge and the Charles River, your next stop will be the USS Constitution.
The frigate ship is made famous thanks to its participation in the War of 1812 against the British. It saw considerable action and if you like, you’ve the option to tour and explore the ship as well.
Which leaves you with just one final stop, the Bunker Hill Monument. It’s also the largest. Obelisk in shape, the monument casts a long shadow over the green grass in front of it. There is a museum across the road for those that would like to learn more about this epic battle of Bunker Hill too.
There ends your Freedom Trail. If you’ve made it with time to spare, take the opportunity to put your feet up before dinner.
Day 1 evening
La Famiglia Giorgio’s
You’ll be heading back to North End for dinner. In Boston’s Little Italy you’ll find an array of excellent Italian restaurants. The pick of the bunch here though would have to be the La Famiglia Giorgio’s. They offer a warm, family style Italian experience. Set inside an iconic Boston brownstone, only non-Italian food lovers will leave here hungry.
La Famiglia Giorgio’s address: 112 Salem St, Boston, MA 02113, United States
Dessert at Mike’s Pastry
Hopefully you’ve saved some room for dessert. You can’t spend 2 days in Boston and not visit Mike’s Pastry, an iconic bakery. Selling oversized cannoli, they serve it up in a variety of flavoured fillings. You can expect a line, it’s popular amongst tourists and locals alike. It can get a little messy eating them, but you won’t regret any of the significant calories you’ll digest.
Mike’s Pastry address: 300 Hanover St, Boston, MA 02113, United States
Day 2 morning
Arise early and head down to the Boston Harbor. There are numerous tours and boat trips you can do, but getting out on the water doesn’t have to be expensive. Take the Charlestown ferry from the Boston Long wharf and pay $US3.70 for a one way trip to Charlestown. The one way trip takes 10 minutes.
Step into the globe
Grab an Uber and your next stop will be the most unique of your visit. The Mary Baker Eddy library’s main attraction is the Mapparium. This interestingly named three story stained glass globe details the Earth whilst you stand at the centre of it. It’s a little off putting, as it feels kind of inside out of how we all come to know a globe.
It is akin to standing at the core of the Earth whilst you admire the world as captured in 1935. For those with a love of travel (for example, us) this is a must do in Boston.
Mary Baker Eddy Library address: 200 Massachusetts Ave, Boston, MA 02115, United States
Take me out to the ballpark
Located around 10 minutes walk from the Mary Baker Eddy library is the home of the Boston Red Sox, Fenway Park. Now I’d recommend if there was a game on during your visit to get yourself along to that. Unfortunately, the Red Sox were out of town playing the World Series on our visit, so a tour of Fenway Park was as close as we were going to get.
Paying a visit to the oldest baseball stadium in the US is a thrill for a Red Sox fan like me. But even the most ardent baseball hater will find things of interest on this tour. Fenway Park is unique in many ways that I won’t ruin, and will at least raise an eyebrow for those with minimal baseball background.
Book your tour well ahead of time, it is a popular tour that people come from the world over to do.
Day 2 lunch
Whilst a hot dog might feel the appropriate lunch time meal after visiting Fenway, hold that appetite. You’re heading over the Harvard with your first stop the Border Café. There’s a great selection of generously portioned Mexican and American fare at this popular restaurant.
Day 2 afternoon
With a full stomach it’s now time to feed your mind. You didn’t come to Harvard just to eat did you? The campus grounds of Harvard University are free to wander about and you can do so at your leisure. Wander between the buildings in the footsteps of Barack and Michelle Obama, Mark Zuckerberg and Al Gore amongst others. It’s probably the easiest part of your 2 days in Boston, and provides a beautiful stroll.
If you like, you can have a Harvard student take you on a personalised walking tour of the grounds. Who knows, maybe you’ll have a future US President or business magnate show you around!
When you’ve finished wandering the campus proper, head down to the Charles River. As the sun goes down, it’s a magical place to watch the rowers go through their paces.
Day 2 evening
There are a truckload of places you can eat in Boston. However, with only 2 days in Boston, a return to Fanueil Hall and Quincy Market makes sense. With its plethora of local food options, you can fill up on something you may have missed at lunch yesterday. Our visit was longer and we returned here knowing the best of Boston sits under the one roof.
Time for a beer and sports watching
Post dinner, sample some of Boston’s finest beers at the Bostonia Public House. If you’re still hungry, they serve up some traditional New England fare here too. This place is classic Boston and has a good range of beers on tap. No matter the season, you can bet there will be some sport on the TV. For your sake, I hope the Celtics, Bruins, Red Sox or Patriots are winning. You’ll find out just how parochial Bostonians can be when it comes to sport otherwise!
Bostonia Public House address: 131 State St, Boston, MA 02110, United States
How to get around during your 2 days in Boston
Public transport
Boston has a good quality public transport system. The T or subway runs through most of the places you’ll want to visit and easily navigated. Tickets can be purchased per ride, (fares from $US2.90 as of September 2019) or you can purchase a Charlie Card to receive a slight discount ($2.40). We rode the T on a couple of occasions and opted for a pay as you go ticket.
Ride share
To maximise our time, we utilised both Uber and Lyft.
On foot
We clocked up a lot of Fitbit steps during our time in Boston. It’s a genuinely enjoyable place to walk and take in the sites and highly recommend this as a way of enjoying the city at a good pace.
How to get to Boston
By air
We flew into Boston Logan International airport. The airport sits around 5 miles outside of central Boston, but the road can be a crawl of traffic. You can catch the T from the airport or alternatively catch the ferry if you’re located near to Boston Harbor.
We always use Skyscanner to compare prices before booking our flights.
By rail
Boston South Station train station is the best hub in Boston with fantastic Amtrak connections to New York and Washington DC. We departed from here to head to New York and it couldn’t have been easier.
When to visit Boston
Isn’t this the million dollar question? As mentioned, we visited during the fall and the colours were spectacular. If the Red Sox are up for it, you might even see them playing in the World Series if you’re lucky.
The different seasons have different attractions of course. There is much to see and do here that isn’t reliant on weather. Unless you’re a fan of the cold though, I’d recommend summer or fall to add outdoor activities. It will also make the Freedom Trail a little more bearable.
Where to stay in Boston
Not unlike most major US cities, Boston has a large amount of hotel accommodation to choose from. We did find it difficult to find good value options until we stumbled across One India Street. Located very near to Faneuil Hall and Bostonia Public House both recommended in our itinerary, this was a great location.
We didn’t have just a room, but a one bedroom apartment. The booking process was a little different. It was technically a short stay apartment and there are some different laws associated with staying here requiring additional paperwork. Aside from that, we paid around half the asking price of a hotel room in most well known hotels. Definitely a thumbs up from us, and that rainy day was well spent in a home away from home.
Other things to consider for your 2 days in Boston
As mentioned, the weather will play a role. Consider what you like to do and whether the elements may play a role in determining a visit. With lots of walking involved, our itinerary is best experienced in bearable weather.
Sports. If you’re a sports lover, check out the schedules of the various teams that call Boston home. If I had one regret, it was not being able to watch some live sport in Boston, but alas that is how our schedule fell. Bostonians love their sport and remind me a lot of Australians in their passion for it. If you can, try and squeeze that into your Boston itinerary.
The Freedom Trail can take as little or as long as you like. As you may have picked up in my detailing of it above, all of the sites are interesting, but some more interesting than others. You might love graveyards and spend a disproportionate amount of time at these stops. You might motor through the first few stops in no time and spend 2 hours at Paul Revere’s home. It’s hard for me to say, but try and make time for at least a passing visit to each.
We loved our time in Boston. Have you been? What did you enjoy that we should add to a future itinerary?
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