We adore Boston, and I love writing detailed travel itineraries–so you’d think this 2 days in Boston itinerary would have been fairly easy to write, right?
Nope!
As it turns out, a full summer of living in and exploring Boston in-depth with the intention of blogging about it resulted in having more favorite things to do in Boston than can be squeezed into a 2 day Boston itinerary–but lots of research and writing later, I managed to whittle down the best of Boston into a 48 hour Boston itinerary.
And, that surprisingly consequential summer led to another reason to return to Boston again and again: my Dad met my fabulous now-stepmom during that visit (hi, Christine!), and with 30 years of living in Boston under her belt, she has brought Boston and New England as a whole into our lives forever (and yes, she has provided many tidbits to help us enhance this Boston itinerary even further).
From someone who spent 3 months living there and fell head-over-heels for the city despite assuming that wouldn’t happen, here is everything we recommend you do–plus all the logistics you need to know–to pull off the perfect 2 days in Boston.
Delicious food, literary interests, American history, pretty neighborhoods, penguins, and more can all be covered with just 2 days in Boston–but fair warning, your feet might be a bit sore at the end!
Table of Contents
- The Ultimate 2 Day Boston Itinerary
- But what about walking the Freedom Trail?
- Don’t want to walk? Consider a Duck Tour.
- Where to Stay in Boston
- The Boston Go Card: Worth the Money?
- Have more than 2 days in Boston, MA?
- Where to Eat in Boston
- Getting Around During a Weekend in Boston
- Read More About Visiting New England (and Beyond)
The Ultimate 2 Day Boston Itinerary
Day 1 in Boston Itinerary: Back Bay, Beacon Hill, and Beyond
Start your morning in the Boston Public Garden.
The Boston Public Garden is one of our favorite places in the city: quiet and beautiful, it’s a great place to relax, take a walk, and enjoy a bit of peace and (relative) quiet in the midst of the hustle and bustle of the city.
Be sure to check out the Make Way for Ducklings Statue, put in place for the famous children’s book that features Boston, while you’re there!
If you’d like to enjoy views of the Boston Public Garden from the water, the swan paddle boats in the garden’s pond are famously inexpensive at $4.50/ride.
Head to Back Bay for brunch and beautiful houses.
Back Bay is one of Boston’s trendiest addresses: here is where you’ll find stunning mansions, high-end shopping, and the occasional burst of surprising quirkiness (like The Fairy Shop, which features oodles of Harry Potter memorabilia and makes my inner eleven-year-old quake with joy).
Here are a few of the best places to check out as you explore Back Bay on foot!
Commonwealth Avenue
Some of the most fashionable addresses in Boston can be found on Commonwealth Avenue!
Stretching into Back Bay from its endpoint at the Boston Public Garden, don’t miss the chance to walk down this stunning street and gawk at the beautiful homes.
This is a fantastic place to start your explorations of Back Bay.
Trinity Church
One of the most beautiful churches in Boston, this 19th-century church sticks out amongst the more modern feel of Back Bay.
Boston Public Library
In addition to being exquisitely beautiful, bibliophiles across the USA owe a debt of gratitude to the Boston Public Library for its continuing advances forward.
This was the first publicly funded library, the first library to open additional branches, the first to lend books out, and more recently, the first to install free wifi.
In other words, they’re pretty cool (and the reading room is a must-see during 2 days in Boston).
Peruse Brattle Bookshop.
As a book lover, I can’t write a 2 days in Boston itinerary without including the epic Brattle Bookshop!
Dating back to 1825 and specializing in used and rare books, Brattle Bookshop is located just off Boston Common and includes three stories and–my favorite–an outdoor courtyard stuffed to the brim with books.
Even if you don’t make it inside, the courtyard is worth seeing. It boasts hundreds of inexpensive, used books (perfect for a cheap souvenir!) and enormous murals that climb the courtyard walls.
Stroll through Boston Common and enjoy views of the Massachusetts State House.
Boston Common is the heart and soul of Boston (and it’s definitely the Common, not the Commons, as locals will be quick to tell you).
Within a few minutes walk you can be in Beacon Hill, Back Bay, at the Massachusetts State House, at the theatre, shopping at Downtown Crossing (this is where you’ll find all the standard chain stores), or exploring a piece of American history.
The park is gorgeous to walk through, too. Be sure to stop by the carousel, take in the views of the gold-domed Massachusetts State House while you’re there, and count how many impeccably groomed golden retrievers you pass (it will be a lot) while you’re there!
Pay a visit to Beacon Hill.
Beacon Hill is my favorite neighborhood to explore in Boston.
This is the Boston you see on postcards: redbrick mansions, black shutters, a cobblestone path or two, tree-lined streets.
It is absolutely stunning to wander through–we recommend walking from Boston Common up to Louisburg Square, which boasts some of the most prestigious addresses in Boston (former Secretary of State John Kerry lives here), and then taking a quick stroll to Acorn Street to take advantage of one of Boston’s most photogenic spots.
Keep in mind that Acorn Street is very popular these days! Make sure to be respectful of people’s property (some residents have complained about visitors using their stoops–best to stick to the cobblestones).
Visit Park Street Church and Granary Burying Ground.
After enjoying a bit of time in Beacon Hill, head back down to Boston Common and pay a visit to the Park Street Church and Granary Burying Ground, which are right next door to the Common.
You’ll notice a large monument with a very familiar name in Granary Burying Ground: Benjamin Franklin’s parents are buried here, and a monument to the family is erected toward the center of the cemetery.
Stop by the King’s Chapel & Burying Ground.
The King’s Chapel is my favorite church in Boston to go inside–not because it is ornate, but because it is so unusual among US churches.
Built originally as an Anglican Church in the 18th century, the church has enclosed “boxes” instead of rows of pews.
Originally, prominent families who were members of the church would have a box of their own that they would sit in each Sunday.
The King’s Chapel still has an active congregation–but these days, instead of Anglicans, Unitarians call the chapel home.
Eat the original Boston Creme Pie at Omni Parker House.
Think you need to make a reservation and sit down to a meal to eat the original Boston Creme Pie?
You definitely don’t!
The Omni Parker House has a small shop on the first floor selling the delicious cakes, and we recommend stopping to pick one up.
If you want to also try the original Parker House rolls (which are, in fact, delicious), consider planning a meal–home to one of Boston’s many historic restaurants–at the Omni Parker House as well.
And, while we’ll talk more about hotels later, suffice it to say that if you’re looking for a luxurious, historic, and centrally-located place to stay in Boston, the Omni Parker House is a great choice.
Take a peek at the Old Corner Bookstore.
The former home of Anne Hutchinson has acted as a bookstore, apothecary, home, Boston Globe souvenir shop, diamond store, and now a Chipotle: talk about evolution!
The building is still worth a nod as you go by, though, and also happens to be set right across from the Irish Famine Memorial–a striking statue worth taking a look at during your 2 days in Boston.
Pay a visit to the Old State House and the site of the Boston Massacre.
As you wander your way through Boston on your way to the Old State House, be sure to note the Old South Meeting House along the way!
The Old State House and the site of the Boston Massacre that is right out front is the perfect final sightseeing stop on your first day in Boston.
As the oldest surviving public building in Boston, the Old State House has seen more than its fair share of American history: it was once the seat of the colonial government, then became the seat of the Massachusetts state government and eventually Boston City Hall.
The Old State House has been a museum since the 19th century, after more than 100 years in public service and a brief stint as a commercial building.
Day 2 in Boston Itinerary: Marketplace District, the North End, and the Waterfront
Begin in the Marketplace District.
The marketplace district is all about the food, so come hungry and ready to explore as you start the second day of your Boston itinerary (just ignore the hideous city hall that’s across the street).
Here are the essential stops to make when visiting Boston’s marketplace district!
Boston Public Market
Looking for some New England specialties, whether to devour immediately or to take home?
Boston Public Market is the perfect spot for that: featuring exclusively New England-based products and companies, you can pick up anything from produce to donuts to crafts here.
This is one of my favorite spots in Boston–and not just because of how good the ice cream is!
Haymarket
If you’re lucky enough to have your 2 days in Boston overlap with a Friday or Saturday, be sure to swing by Haymarket (located right in front of the Boston Public Market) to check out a fabulous farmer’s market!
Faneuil Hall Marketplace
Made up of closely located Faneuil Hall, Quincy Market, South Market, and North Market, this is the heart of Boston’s historic market district–and also one of the most touristy places in the USA.
While we definitely feel it’s worth stopping by during your 2 days in Boston to appreciate the markets and the history behind them (Faneuil Hall dates back to the 18th century), unless crowds, chain stores, and overpriced food are your thing, you won’t need to stick around long.
Stop by the New England Holocaust Memorial.
Right in between the Boston Public Market/Haymarket area and the Faneuil Hall Marketplace sits the sobering New England Holocaust Memorial.
It takes very little time to walk through–no line, no entrance fee–but it is worth taking a moment to slow down and appreciate it.
Head into the North End.
Boston’s North End (also known as “Little Italy”, though you won’t catch a local calling it that) is the oldest neighborhood in Boston and a fascinating sort of place.
It’s one of the oldest parts of Boston, and is famous for being a neighborhood popular with Italian immigrants, though there are more tourists than Italians there these days.
It’s home to tons of Italian food (from the very good to the very bad), beautiful architecture, several noteworthy spots in American history, and a couple of very famous pastry shops.
Paul Revere House
The oldest remaining building in downtown Boston once belonged to none other than Paul Revere!
Whether you head inside for a tour or simply admire the facade as you walk by during your 2 days in Boston, be sure to note this piece of American history sitting in the North End.
Old North Church
And speaking of Paul Revere…
The whole “one if by land, two if by sea” story? That lantern was said to have been hung here, at the Old North Church.
(Modern note: there is a popular scam around the world that consists of fake monks collecting money–and they have a big presence right here. Best not to engage with them!).
Copp’s Hill Burying Ground and the Spite House
Boston’s second-oldest cemetery holds more than 1200 marked graves that include plenty of notable burials from the colonial era… but that’s not the only reason to visit.
Right across from Copp’s Hill Burying Ground sits the Spite House (also known as the Skinny House), which is home to one of my favorite Boston stories.
As the story goes, two brothers inherited land from their father. While one was away serving in the American Civil War, the other brother built a large home, taking over part of the soldier’s inheritance.
When the soldier returned home, he built the “Spite House”–incredibly skinny, and yet incredibly effective at blocking his brother’s view.
The legitimacy of the story is somewhat questionable, but it sure is a classic Boston tale.
Mike’s Pastry and/or Modern Pastry
If you’ve heard one thing about eating cannoli in the North End, it’s probably about how delicious Mike’s Pastry is.
If you’ve heard two things, it’s probably that Modern Pastry is better and more “unknown”.
Here’s what we can tell you firsthand: Modern Pastry is tasty, and the line at Mike’s Pastry was always too long for us to bother with (though we’ve heard from others it dies down sometimes–if you visit in the offseason, you might get lucky!).
And, if you are looking for a fantastic interior and an atmosphere that feels slightly like actually being in Italy, Caffé Vittoria is an even better option, though I’d have to do a back-to-back comparison to offer an opinion on the pastries (all of these places have tasty treats, though).
Regardless of where you choose to get one, we certainly recommend eating a cannoli or two during your 2 days in Boston.
Take a whale-watching cruise or visit the penguins at the New England Aquarium.
It doesn’t get more classic New England than a whale-watching cruise!
While the cruises require a bit of a time commitment (3-4 hours), if you’re hoping to hit the water during your weekend in Boston, a whale-watching cruise like this is an incredibly memorable option.
Of course, like all attractions involving animals in the wild, there’s no guarantee regarding how many whales you’ll see–but so many whales call Boston home that your odds are much better here than in many popular whale-watching ports around the world, to the point that many captains even guarantee at least one sighting during a trip.
Prefer to stay on dry land, or visiting Boston in the dead of winter when whale cruises aren’t available? If so, the New England Aquarium is one of the best aquariums we have ever been to.
There’s a huge emphasis on conservation, the exhibits are striking and education-focused, and the aquarium’s location on the harbor means that it is even able to use the natural seawater for some of its exhibits!
Though the five-story ocean tank, complete with an ancient sea turtle named Myrtle, is incredible, the real showstopper for us is the penguins.
We adore penguins, and the New England Aquarium is home to several species.
If you want to see something truly adorable, visit the aquarium at 9:00 AM or 2:30 PM–aka penguin feeding time.
Want to avoid waiting? Purchase a skip-the-line aquarium ticket before you get there!
Take a stroll along the Harborwalk.
At around 43 miles long, you definitely won’t see even a quarter of the Harborwalk with only 2 days in Boston–but this continuous trail along Boston’s coastline is definitely worth checking out for a little bit.
Luckily, the New England Aquarium is located right on it, making it easy to go for a walk before or after your visit.
Enjoy the sunset from the water with a harbor cruise and/or dinner in the North End.
The perfect end to a 2 day Boston trip isn’t in Boston at all–it’s in the water, staring back at the city that boasts one of my favorite skylines in the world.
If you didn’t already take a whale-watching cruise, we recommend taking a harbor cruise around sunset to enjoy the end of the day.
Cruises are available at literally all price points, from a basic group cruise in a shared boat to a memorable cruise on a tall ship and beyond.
For a less expensive harbor cruise, this sunset cruise is a great option!
Had enough of the water for today–or want to enjoy a fabulous dinner after the boat ride?
If so, consider saying goodbye to Boston with a fabulous Italian-American dinner in the North End.
Like many iconic neighborhoods around the world, you’ll find a mix of mediocre-to-terrible tourist traps and delicious restaurants here, so it’s imperative to check reviews before sitting down!
We have loved our experiences at both Ristorante Euno and Tresca (pictured below: everything was delicious, but their house special of chicken parm made with vodka sauce was a standout!).
But what about walking the Freedom Trail?
If you know one thing about what to do in Boston, it’s probably the Freedom Trail.
The famous 2.5-mile trail covers 16 historical sights related to American history in Boston and is easily one of the most popular things to do in the city.
So don’t worry–it’s definitely on the list!
In fact, 14 of the 16 sights on the Freedom Trail are covered in this 2 days in Boston itinerary, including Boston Common, Park Street Church, King’s Chapel, Faneuil Hall, every historical sight I discuss in the North End, and more.
If you follow this itinerary during your weekend in Boston, you’ll spend quite a bit of time walking the Freedom Trail, and you’ll have tons of opportunities to check out the brick markings that denote where it leads!
Rather than simply list something so vague and malleable on our 2 days in Boston itinerary, though, we wanted to be sure to give specific suggestions.
After all, the trail can be seen in any order and doesn’t need to be done all at once.
Don’t want to walk? Consider a Duck Tour.
Cheesy? Yes.
Entertaining? Absolutely.
Boston’s Duck Tours are famous for the unmistakable truck-slash-boat contraptions that they cart tourists around in by both land and sea.
Corniness aside, if you’re looking for an excellent way to get an overview of Boston’s most famous sights and history without too much walking, signing up for a Duck Tour might be the right choice for you!
The tours do sell out, especially in the summer, so be sure to book in advance if you want to make a Duck Tour part of your 2 days in Boston itinerary!
Book your Boston Duck Tour today!
Where to Stay in Boston
With only 2 days in Boston, we recommend staying somewhere close to the T (aka Boston’s subway) that is near the center of the action.
The North End is a tempting option, but it is fairly difficult to get in and out of. Instead, we’d recommend staying somewhere in Back Bay or the Historic Downtown if possible. The Theatre District (near Downtown Crossing and Chinatown) is another solid option with a great central location.
If budget is an issue, you may need to go a bit further out. That’s not a problem–just make sure you’re within walking distance of a T stop!
For budget travelers not willing to sacrifice on location, the HI Boston Hostel is a great option.
Mid-range travelers will love the location (and breakfast) at the Boston Park Plaza.
Want access to a kitchenette in your room? Copley House features some studios and apartments!
For travelers looking to splurge, the Boston Omni Parker House Hotel has it all: history, a prime location on the Freedom Trail, plenty of ambiance, and of course, the original Parker House rolls and Boston cream pie served right on-site.
Check rates & book your stay in Boston today!
The Boston Go Card: Worth the Money?
The Boston Go Card is promoted as an all-access pass, allowing you to buy included and/or discounted tickets to dozens of Boston attractions at once.
With this 2 days in Boston itinerary, you won’t need it: the 2-day pass won’t allow you to break even or get ahead with the attractions we opted to include here (after all, so much of Boston is about exploring outside, on foot–which is free).
However, if you’re staying in Boston longer, or you are interested in participating in a Hop On/Hop Off trolley tour, completing a Fenway Park tour, visiting View Boston on top of the Prudential Tower (the new version of the old Skywalk Observatory), or visiting several museums, then the Boston Go Card is probably the right option for you.
Find out more about the Boston Go Card and see if it’s right for you!
Have more than 2 days in Boston, MA?
Boston is full of things to do: even after 3 months in the city, plus return trips, we still have a list of unchecked Boston bucket list items longer than we would like.
If you’re lucky enough to have more than 2 days in Boston, consider visiting Revere Beach (it’s the oldest public beach in the USA!), touring the Samuel Adams Brewery, attending a Boston Red Sox game (or just touring Fenway Park, the oldest baseball stadium in the USA), taking a walk along the Charles River Esplanade, or heading out a bit farther along the Freedom Trail to take in the two remaining sights not covered on this itinerary, the USS Constitution and the Bunker Hill Memorial.
If you’re a museum fan, Boston has enough to keep you occupied for months: for example, the Isabella Stewart Gardner Museum is built in the form of a Venetian palace, holds gorgeous artwork, and is the victim of a heist.
For science lovers, the home of MIT and Harvard has you covered: the Boston Science Museum and MIT Museum are both worthy of a visit.
With time to plan in advance, consider going stargazing at the Coit Observatory.
If you’re visiting in the summer, a visit to the Harbor Islands is always a good idea for nature lovers.
Looking for day trip ideas? Salem, Rockport, Newport, Concord, and Lexington are all popular for good reason, and less-iconic but gorgeous New England beach towns like Hingham, Cohasset, and Hull offer less-crowded and more easily accessible day trip options than the Cape.
I could keep going forever, but suffice it to say: you can do a lot with only 2 days in Boston, but you can’t do it all!
Where to Eat in Boston
We are far from experts on Boston cuisine, but we have had some truly stellar meals in Boston... and also asked my stepmom to help us round this section out a bit.
Here are some delicious restaurants that can easily fit into your 2 days in Boston itinerary!
Buttermilk & Bourbon — Commonwealth Avenue (Back Bay)
I love biscuits.
More than that, I love southern biscuits, and I’ve been eating them all my life, in North Carolina and beyond.
So when I say that Buttermilk & Bourbon serves southern-style biscuits so delicious that I still think of them fondly a year later, I really mean it.
All of the food we had was incredible, and we can’t recommend their brunch enough (and I assume lunch and dinner are fabulous as well).
Neptune Oyster — Salem Street #1 (North End)
I’m not a huge oyster fan, but Jeremy sure enjoyed these (and the lobster roll he happily consumed after downing the oysters).
A friend of ours took us here when she came to visit us in Boston, touting it as one of her favorite restaurants–and judging by the fact that she looked to be having almost a religious experience the entire time she was eating their oysters, it’s a well-earned spot on her list.
As the resident non-oyster eater, I can attest that their burger was delicious.
Ristorante Euno — Salem Street (North End)
Many Italian restaurants in the North End are duds.
Ristorante Euno is not one of them–in fact, this is the only restaurant in the USA we have eaten in that even begins to approximate having dinner in Italy.
We ate here with a big group and had the opportunity to taste everything from several kinds of pasta to veal to steak to we-stopped-counting-at-some-point amounts of wine, and it was all delicious.
Tresca — Hanover Street (North End)
I mentioned this restaurant above as well, but it’s worth repeating!
Offering a more modern twist on Italian food, Tresca draws inspiration from Tuscany in particular (though is solidly Italian American food, not traditional Italian).
The food, service, and ambiance were all excellent, and you can’t go wrong ordering the chicken parm with the house vodka sauce!
Tatte Bakery and Cafe — Charles Street (Beacon Hill)
Tatte Bakery & Cafe has several locations around Boston (and they’ve even expanded to the DC area since we first ate there), but the Beacon Hill location is easy to reach as part of your 2 days in Boston itinerary!
Home to delicious sweets, tasty sandwiches (I had a brie and prosciutto sandwich that was incredible), and pastries that look too beautiful to eat, Tatte Bakery is a great place for a snack or quick lunch while you’re running around trying to see Boston in 2 days.
Bell in Hand Tavern — Union Street (Marketplace District)
America’s oldest tavern has been pouring ale since 1795, so you’d assume that puts them at risk of being gimmicky with mediocre food, but nope!
We never had a bad dish at Bell in Hand Tavern, and their burgers are incredible.
If you’re hungry while in the marketplace district, this is the stop for you!
Union Oyster House — Union Street (Marketplace District)
Right across the street from America’s oldest tavern sits America’s oldest restaurant, which has been serving up seafood (and especially New England chowder) since 1826.
We didn’t eat here personally, and reviews are mixed–some say the food is excellent, some say it is just okay. Most agree that you’re paying a bit more to eat at a historical location, which is not surprising.
Regardless of the ups and downs, though, I couldn’t bear to leave it off–even if you just snap a photo of the exterior as you walk by on the Freedom Trail, it’s worth being aware of this landmark during your 2 days in Boston.
La Voile — Newbury Street (Back Bay)
Looking for delicious French food served in a beautiful setting?
If so, head to Back Bay to indulge at La Voile, where you can either order a la carte or opt for the nightly 3-course prix fixe menu.
You can enjoy your meal either indoors or outdoors, weather permitting, though you may want to make a reservation if you have a preference!
Parker’s Restaurant at Omni Parker House — School Street (Historic Downtown)
I’ll admit: the main dishes here were good-not-great for the prices they charge… but gorging ourselves on the original (and delicious) Parker House Rolls and Boston Cream Pie made us glad we experienced the food once.
If you want to try out Parker’s House, we recommend going for lunch or brunch to keep costs down a bit.
Dunkin’ Donuts — Literally Everywhere
… Or is that just “Dunkin'” now?
Okay, this is (mostly) on here as a joke–but okay donuts and subpar coffee aside, there’s no denying that grabbing a coffee at Dunkin’ is a true Boston cultural experience.
Getting Around During a Weekend in Boston
Boston is consistently rated as one of the most walkable cities in the USA and is also home to one of the densest public transportation networks in the country.
During our 3 months in Boston, we relied exclusively on the subway, the occasional bus, and our feet to get around the city, and we recommend you do the same during your 2 days in Boston.
There are two ways to buy tickets to the T, aka the subway/metro system: with a CharlieCard or CharlieTicket (which are free and reloadable), and individually.
The CharlieCards can be picked up from any attendant in the subway stations, but they aren’t always available.
While they can making paying for the T simpler, with only 2 days in Boston, I wouldn’t worry too much about getting one.
Bonus piece of history: if you ride the Green Line of Boston’s metro system, specifically between Park Street and Boylston, you’ll be riding on one of the oldest metros in the world (and arguably the oldest one in the USA).
Read More About Visiting New England (and Beyond)
Excited to hit the road soon and ready to keep planning your trip?
You can browse our 100+ blog posts about traveling in the USA here, or check out these guides:
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- 21+ Best Places to Visit in November in the USA (Fall Vacation Ideas!)
- 15 Wicked Fun Quotes About Boston
- USA Bucket List: 50 Best Places to Visit in the US
- 13 Epic East Coast Cities for Weekend Getaways
I’ve never been to Boston before but I would love to see Beacon Hill in person. It looks beautiful from the photos in your post. I also have a slight obsession with Boston Creme Pies so that’s a must try as well lol
Haha, yes, it definitely is! There are SO MANY amazing Boston Creme Pies in Boston… including in Beacon Hill! 😉
Thank you so much for the time you spent in Boston so I could so easily enjoy the city on a quick stop. Your writing is engaging and your personal insights and recommendations so valuable. I have saved your site for future trips.
Thanks so much, Connie! We appreciate you reading. 🙂
Hi! Great Itinerary!
I’m heading to Boston this Friday for a week and I’m super excited to check out these places 🙂
Thanks so much, Evelyn!
Hope you have an amazing time during your trip to Boston! 🙂
loved your page with all its information. I have a question : we are going to be staying at the North End soon at Battery Wharf , what is the fastest way to Salem ? I have heard there is a train from the North End straight to Salem. But I am really confused. Can you tell me your opinion ? I have copied your page and will use it for my trip.
Thanks
Hi Kathy! Thanks for reading. 🙂
Yes, a train runs from North Station (which is essentially right next door to the North End, it’s a quick walk away) directly to Salem. It’s a commuter rail, so very dependable and easy to use. We visited Salem that way personally and had no issues–it takes a little over half an hour to get there if I remember correctly.
Brilliantly written. Unfortunately not many of the pique my interest. Definitely worth the read and also learn a few things. Love it!
Thank you for this 2-day itinerary! We are looking forward to our time in Boston, and this will help us make the most of our short time there.
So glad we could help, Regina! Have a great time in Boston. 🙂
Hi! Thanks for the info. Invaluable! Question. Can this be done easily on bikes or at least the harbor walk? Do you think we could fit in a Sam Adams tour in? What would you cut out?
So glad you found it helpful, Milissa! Yes, the Harborwalk is also a bike path, you can definitely ride there.
You can definitely rearrange things to fit a Sam Adams tour in! As for what to cut, it’s completely up to what you guys most prefer–I adored the penguins, for example, but some people wouldn’t care about the aquarium at all.
Some of the sites, such as Faneuil Hall or the Boston Common, can take anywhere from a few minutes to get a quick look at to an hour or more of perusing it in detail, so there’s a lot of flexibility with timing built in depending on your tastes.
Beacon hill is a tough pedal up, otherwise biking is fairly easy, although bike lanes are inconsistent.
I’d personally prioritize the uss constitution. It’s a free tour and think they are going below decks again as they weren’t for a while during covid.
Sam Adams is a good tour, but I might recommend harpoon instead. It’s closer, is almost as old, and is still local.
Hi,
My husband & I will be in Boston in October for two days and I love this itinerary! Great job! So we’ll written! Thank you for sharing!
One question… we will have a rental car and driving from Freeport, Maine. What is the best place to stay, B&B preferably, so that we can just walk from our B&B to all of these sites… and just leave our car at our B&B. Is that possible?
We plan on driving to Plymouth and onto Rhode Island and then Connecticut after our time in Boston.
Thank you for your help and suggestions,
Pam
Thanks so much, Pam!
I’m not familiar with any BNBs off the top of my head that would meet both of those needs–generally, if you’re staying close enough into town to be within walking distance of the sights, small BNBs will have limited or no parking available.
I’d recommend plugging your requirements into your preferred hotel booking site (we use Booking dot com), including parking as a requirement, and seeing if anything pops up in a central neighborhood.
That being said, you can also park (paid, but convenient) in the garage under the Boston Common, which is very convenient for sightseeing!
Great post! Just what I was looking for. Real advice from a real person. Thanks for all of the great tips and restaurant suggestions.
Thanks so much, Andrea! Hope you guys love Boston as much as we do!
I love your post. Me and my husband will use your itinerary this weekend. Please give us suggestions of the hotels we can stay. We will be driving from Hanover NH and plan to park the car in the hotel, and we will just walk to all the places you mentioned for 2 days. Please let me know of your hotel suggestions. Thank you so much for your help.
Hi Susan! We have a few hotel recommendations in the post, after the itinerary section.:-)
Great review of my beloved city!!! But… I’m not sure how you could focus on Back Bay and not mention Newbury Street–filled with some of Boston’s best shopping and restaurants. Also, since I am a local, we would never refer to the T (formally known as the MBTA) as a metro. Honestly, if you said “metro” to any Bostonian, we wouldn’t know what you were talking about. Lol. Thank you for appreciating all the beauty Boston has to offer!!
Thanks so much, Patty! I hadn’t realized we didn’t mention Newbury Street in this post–it’s in our things to do in Boston post, though. 🙂 Beautiful street, I love it there!
Great 2 days itinerary!Really useful tips and informative content about boston.Thanks for sharing.
Hi Kate – loved the write up! We came to Boston in 2010 and fell in love with the town – and hence, have stayed on. If you ever edit the article – do please consider adding two great experiences: (1) that the Boston Library has one of the finest “afternoon tea” experiences in the world but has to be booked 4+ months in advance and 2) the nearby towns of Lexington (I live here) and Concord still have a ton of historical sites and ceremonies connected to the first revolutionary war… and are just 20-25 Min away at most from Boston Backbay.
I’ve had the Boston Library tea on my bucket list for years! One of my friends got to do it and raved about it. 🙂 Maybe next time!
This article and guide has been fabulous. My cousin and I are planning our first trip to Boston. It will be short, two and half days, prior to boarding a cruise ship. I cannot thank you enough for making it easy to map out, for the recommendations of places to eat and stay and for the history and photos. We want to make sure and hit all the highlights and to see the real Boston. This covers it all. Over the top great and I am so very thankful!!!
It makes my day to hear that, Sharon! Hope you and your cousin have a fantastic couple of days in Boston! 🙂
Thank you for this post! My husband and I will be first-timers in Boston in October (14-18), and I was wondering if there are any fall specific activities/sights you’d recommend?
Hi Becky,
The main thing will simply be to appreciate the foliage, which you should definitely see! I’d plan to spend extra time in the parks, burying grounds, etc, as they’ll all be decked out in color.
If you have a chance to take a day trip outside of Boston, apple-picking (and apple-cider-donut eating) is a classic fall activity with plenty of options close to Boston. 🙂
Salem is ridiculously crowded in October, of course, but it’s also an easy day trip from Boston, and arguably there’s no better time to visit than October! The whole town goes all-in on spooky season.
Thanks so much for this information! We will be traveling with my parents, and will have a couple of days in Boston. Mom gets around fine, but occasionally has trouble with her knees. Would you recommend a hop on/hop off bus or the duck tour instead of walking? I’m wondering about steep hills, and stairs – things of that nature. I am just asking for a general idea – I realize you have no way to assess someone’s abilities, lol!
Your blog post will be a great help!
Hi Katie,
So glad you’ve found it helpful!
Much of the route is fairly flat, but Beacon Hill in particular has very steep sections–I’d be on the lookout for that.
A hop on/hop off tour might be a great compromise between going alone versus a fully scheduled option like a duck tour, as you can walk as much as makes sense but also always have another stop fairly close by. That way, you don’t have to commit to an enormous amount of walking at one time if energy starts to wane.
My husband and I are planning to spend a weekend in Boston. This itinerary looks fantastic.
We booked a B&B nearby the Aquarium- so the penguins and the Harborwalk a must. Definitely to walk off the Boston Creme pies/biscuits and lobster rolls we plan on eating. And we will try to get in a Sam Adams Tour. One of my favorite parts of your suggestions was the Book stops: I also read about “Boston Athenaeum” – but need to reserve a tour to see the building.
And to add to the Mix- we reserved a show at the Opera House also. The theatres are absolutely amazing.
If I could ask for a suggestion, please? Can you provide a walking map to follow. Not being from Boston- I am a little confused if I could find all these areas by the GPS on my phone. But from what I read0 Boston is a very easy city to navigate by foot and Train.
Thank you for these wonderful ideas- I found this info extremely helpful
Would you recommend the Mapoparium- the stained-glass globe? Thats sounds interesting for a short visit.
I printed out this itinerary and plan on following it precisely. – with a couple of additions.
There is so much to see and do- I am not sure we can fit everything in.
Thanks
Hi,
So glad you found our itinerary helpful!
As far as a map goes, we’ll look at adding one in in the future, thanks for the recommendation. 🙂 If you’re worried, I’d recommend “starring” or adding the places to your GPS even before arriving in Boston–it helps a lot, especially when it comes to knowing what’s close by that you were interested in!
We love the Mapparium (it’s highlighted in our Boston bucket list post), but didn’t include it here simply for lack of time. If it’s something you’re interested in seeing, though, you can easily add it to your weekend!