The Ultimate Boston One-Day Itinerary
Updated: Mar 7
How to see the best of Boston (& a little of Cambridge!) if you only have one day in town...
Boston will forever be my favorite city. Hands down, no contest. I moved to Boston in 2015 for work and overnight became a city girl. I love everything this beautiful, bustling, historic city has to offer and will talk your ear off about it if you let me!
Over the years I had countless friends visit me (and stay in my tiny apartment with 3 other roommates...bless their souls), and I have taken them all on a variation of the one-day tour you're about to read below. For some, we truly only had one day to see as much as possible of Boston. For others, this tour was more of an introduction to the city. I brought my husband J on a similar tour for our first date (and his first time in Boston!) and led a group of 10 friends around to see the same sites three days before me and J's wedding. So you might say I've had the opportunity to perfect this route...
Now, I may be biased from my time living in Cambridge, but I feel strongly that a complete day-tour of Boston begins in Harvard Square.
During my time working in Boston, I actually lived just north in Cambridge, MA (yes, the home of Harvard University). Cambridge is just over the Charles River from Boston proper and on all the same subway lines. Now, I may be biased from my time living there, but I feel strongly that a complete day-tour of Boston begins in Harvard Square, Cambridge. Although the home for this prestigious school is outside of Boston proper, you’d be remiss if you didn’t at least wander through Harvard Yard to admire the stately brick buildings where some of the greatest minds in the world have studied. So grab your most comfortable walking shoes (you'll thank me later) and let's explore!
In this article:
Tips before you begin:
Boston has a very simple and helpful subway system, the MBTA, affectionately called 'the T' for short. As far as public transportation goes, the T is easy to figure out, inexpensive, and (fairly) reliable. The Red Line is far and away accepted as the best line, and conveniently most of the best sites to see in Boston are just a short walk from this line! I highly recommend taking the T as much as you can; besides saving you a bundle on Ubers & Lyfts, many times it will get you to your destination faster than slogging through traffic on the roads.
NOTE: each T line runs between two locations, as labeled on the cars and digital signs. Make sure you know the direction you are heading before you hop on a subway going the wrong way!
Stop 1: Breakfast in Harvard Square
Harvard Yard > swipe for more
Off the T: Red Line, Harvard Square stop
In true old city style, Boston, Cambridge, and many of the surrounding towns are still organized by their historic 'squares'. You'll undoubtedly see many of them if you spend much time exploring the area. Harvard Square is both the center intersection of Massachusetts Avenue (Mass Ave) and John F. Kennedy Street and the collective name for the greater concentric area surrounding these roads.
If you come prepared with a little more time (and a sweet tooth!) head down Mass Ave for breakfast or brunch from Zinneken’s. Zinneken’s serves “Belgian waffles made by real Belgians,” as their slogan boasts and holy smokes are they tasty!! Order them loaded up with fruit or syrups or enjoy plain because even their batter is just so delicious!
If you’re short on time, grab a coffee and a pastry at one of Boston’s favorite cafes, Tatte, to wander with. From breakfast sandwiches to muffins, Tatte (sounds like 'latte') serves familiar favorites throughout Boston, Cambridge, and Brookline.
Harvard Yard is impossible to miss, with imposing gates and a brick wall barricading the cinematically familiar courtyard from the rest of the city. Visitors are allowed to enter the campus most days, but most of the buildings are closed to the public. Having lived a mile from Harvard during my time in Cambridge, I loved coming here to run, enjoy the first snow of winter, or when I just felt like walking through a piece of history.
Although there is much more one can do in Harvard Square (stay tuned for a Best of Harvard Square list soon!) we have a busy day ahead – so gotta keep moving! Hop back on the T (towards BRAINTREE) and settle in for the next 3 stops. Your next destination is CHARLES/MGH.
*Local's Tip* If you can get a window seat on the right of the train, snag it! Immediately before you reach the CHARLES/MGH stop you’ll pass over the Longfellow Bridge, which shows off my absolute favorite view of the skyline (above). Which is saying something, since I’ve made a game of trying all the roof decks in Boston - post coming soon!
Stop 2: Beacon Hill
Off the T: Red Line, Charles/MGH stop
Known for its gorgeous Victorian & Federal style homes, cobblestones, and sometimes impossibly narrow streets, Beacon Hill may be what you have in mind when you picture Beantown.
As you leave the CHARLES/MGH T platform, head down Charles Street & stop at any of the antique stores and other local shops that catch your eye. While there are dozens of streets you can wander down to admire architecture, be sure to find Acorn Street (ft. in our engagement photo above), which has been labeled “the most photographed street in America.” Don’t linger too long though! For some reason the residents don’t seem to like tourists much…
Your jaunt down Charles Street will ultimately take you to Boston Common & Boston Public Gardens- two separate parks side-by-side.
You are currently STEPS away from the famous Cheers bar! I must admit to you that the interior of this bar looks nothing like the staged version from your childhood, however, you’ll immediately recognize the curved stairs leading below ground from the opening credits. "Making your way in the world today….”
East entrance to Boston Public Garden
On a beautiful spring/summer day, I like to start at the garden first and do a pass through to see what’s blooming. My favorites are the giant purple alliums on the west side of the park. The Public Garden is also known for its bright tulips in the spring, signature foot bridge, and large collection of tree species including several stately weeping willows.
The Public Gardens boasts the iconic swan boats, which have taken visitors around the central lagoon for over 100 years. Definitely snap a photograph of the boats (and the real swans!), but I recommend strolling around the garden instead of going for a paddle.
Keep an eye out for the Make Way for Ducklings statue as well! The little bronze animals based (on the children’s story book where Mrs. Mallard leads her ducklings safely from the Charles River to the Boston Public Garden lagoon) are often dressed up for holidays or whichever Boston sports team is currently winning.
Swan boats paddling tourists leisurely around the lagoon
Boston Public Garden in the fall
When you've made a loop of the Public Garden, enter out the east gate and cross the street to Boston Common. ‘The Commons’, the beautiful, sprawling greenspace in the middle of this bustling city, was actually the first city park in America. Here you’ll find fountains and gazebos, winter skating ponds, and even a carousel! Walk through the park or around the outermost paved path to the far northeast corner of the Commons. You’ll see the gold dome of the current Massachusetts State House poking out from the trees. Climb the stairs for a photoshoot spot with either the capitol or the park behind you.
Boston Commons lined with flags for Memorial Day
Stop 3: The Start of the Freedom Trail
Statue of Benjamin Franklin outside of the Boston Latin School site
Corner of Tremont Street and West Street
Now that you are caffeinated and oriented, it’s time to begin the Freedom Trail. This red brick trail begins on the east side of Boston Common and heads north to some of the most historic sites of the city. If you're at the State House you should already see a red brick path at your feet leading down the hill.
Just follow the red brick road… (it’s stuck in your head now too, you’re welcome).
The Freedom Trail technically has 16 stops along its route. I’ve walked the trail countless times, and since we’re moving right along and trying to fit as much as possible into one day, I am going to recommend skipping a few of the more mundane stops in order to keep us moving!
Got an early start and want to see it all? Find the full list and history of the Freedom Trail stops here and soak it all in! You can jump back to my tour recommendations below at the section titled "North End".
The first historic site you’ll come upon is Granary Burial Grounds. I love an old cemetery, and this one boasts many of the famous founders of our country, including Paul Revere, Samuel Adams, John Hancock, and Mother Goose (yes you read that right, she was a real person!). Depending on when you visit, there may a volunteer handing out maps right outside the gate with info about the cemetery. Feel free to take one if you’re a history buff like me, but don’t forget to return it on your way out.
King's Chapel Burying Ground
The next stop on the Freedom Trail is King’s Chapel. This beautiful church is one of two historic churches on the Freedom Trail, and due to the fact that the Old North Church (of Paul Revere fame) is the more well-known of the two, my advice would be to save your time and money for that tour. King’s Chapel was established in 1686 as the first Anglican church in the northern colonies. They boast the first pipe organ in America, as well as the oldest pulpit still in continual use.
The entrance fee for a self-guided tour is $5 per person, and guided tours are offered on the hour for $10 per person. You can reserve your tickets in advance here.
If you have some extra time, feel free to wander the old King’s Church graveyard. Although you will not find as many famous names as in Granary Burial Grounds, the graveyard itself is beautiful to observe simply as a relic of the past.
The next Freedom Trail stops after King’s Chapel are the Boston Latin School and the Old Corner Bookstore. In favor of spending more time at other locations, and since the Bookstore is now leased to a restaurant chain, I recommend moving quickly past these stops and on to the Old Meeting House. Keep following that red brick path!
Old State House
The Old South Meeting House, Old State House, and the site of the Boston Massacre are next. These buildings stand stately and proud among the modern skyscrapers that flank them on every direction. If you squint just a little and use your imagination, you can almost picture a time where they were the most imposing structures for miles.
You can explore both the Old South Meeting House and the Old State House museums with the purchase of a $15 ticket (good for admission to both exhibits) or just continue around to the back of the Old State House to see the site of the Boston Massacre of history book fame. Although the busy streets bustle loudly in every direction now, a medallion marks the spot just steps away from where the fateful event took place on March 5, 1770. Pretty incredible piece of history right at your feet!
Follow the Freedom Trail about .2 miles to Faneuil Hall next. The ground floor of this historic building now houses trinket shops and other retail, but circling around back you’ll find doors leading to the open forum meeting hall on the second floor. Innumerable debates have been held in this very room over the years, starting with arguments against the Stamp Act in 1764. Take a minute to stop and soak in the history.
If you time it right, you’ll often be able to catch a piece of a National Parks Service ranger’s talk about the building and its fame. They do an excellent job, so take a seat and to listen and soak in the history!
Stop 4: Lunch at Quincy Market
Across the street from Faneuil Hall is Quincy Market, the perfect place to grab a bite to eat for lunch! Quincy Market has been a marketplace since 1864 when the structure was built to enclose the previously open-air market hosted on the same spot. When you enter, you will see the same stall-like layout that would have been used by vendors for over 100 years. When originally built, the harbor would have nearly reached the back of Quincy Market’s South Building, but over time Boston has expanded its footprint by filling in the area beyond.
There are innumerable food options available inside Quincy Market, but my go-to is always a cup of clam chowder from one of the half-dozen or so seafood stalls. If you truly only have one day in Boston, you really can’t leave without some chowdah! In the middle of the North and South Market is a large circular open eating area with a balcony and beautiful overhead dome. Tables fill up quickly on both floors, so if you can’t find a seat inside you can most likely find a bench or some steps outside to rest and enjoy your food.
J enjoying another New England delicacy, a lobstah roll, on the Quincy Market steps
If you truly only have one day in Boston, you really can’t leave without some chowdah!
When you’re done eating (and people watching), hop off the Freedom Trail for a minute to check out Christopher Columbus Waterfront Park and catch a glimpse of the Boston Harbor. This greenscape is a classic Boston photo stop with its wharf views and a trellis that's lush & green in the summer and lit with twinkle lights in the winter.
Once you’ve carefully crossed the Fitzgerald Expressway, you’ve made it to the North End! Our last two stops on our whirlwind highlight tour of the Freedom Trail will be Paul Revere’s House and the Old North Church, but before we end there you won't want to miss seeing the Boston skyline from the water!
Stop 5: Boston Harbor Tour
Alongside Christopher Columbus Park is Long Wharf, the launching point of Boston Harbor Island Tours! As long as you still have a few hours left in your Boston day, I highly recommend getting tickets for the ferry. Even if you don't have time to explore the islands, the boat ride itself is a great way to view the city from another vantage point.
Even if you don't have time to explore the islands, the boat ride itself is a great way to view the city from another vantage point.
The Boston Harbor Islands are just a 30-45 min ferry ride from shore and are a fun outdoor adventure break from our otherwise urban city tour! The harbor ferry leaves every couple hours (schedule here) and travels first to Spectacle Island, then on to Georges Island. The cost is about $25 for a round trip ticket which can be purchased online or at the dock. You can choose to stay as long as you want on either island as long as you catch the last ferry back at the end of the day!
Spectacle Island has had several proposed uses over the years, but is now a lovely spot for hiking, picnicking, and swimming. There is a Visitor Center on the island as well, but all trash is carry-in, carry-out. Grilling is also not allowed.
Georges Island is one of Boston's best kept secrets, in my opinion! The island is home to Fort Warren, a Civil War era fort that was subsequently used to train soldiers for many years (and through many wars) after it was completed. There is so much to see! Fort Warren is great for both history buffs and kids. If possible, plan to spend 1-2 hours on the island, but don't miss your boat back to Boston!
I've been to the Boston Harbor Islands several times. All told, I've probably spent the longest time (3+ hours) at Fort Georges. There is just so much to see and explore! For this trip though, I recommend just taking the ferry out and back for the view and the fun of a boat ride to break up the day.
When you've disembarked and walked off your sea legs, you're on to your last few stops in the North End, starting with Paul Revere's House!
Stop 6: The North End
Paul Revere's House
Walk to: North Square & Hanover Street
A brownish/grey wooden structure sandwiched between several other old brick buildings, Paul Revere’s House has been standing on this site since around 1680. Now, I am a huge history buff, but even I’d recommend going to see the house but passing up the tour. Although it is exciting to walk the same rooms as a man who played such a pivotal role in Revolutionary War tradition, the house is rather small and does not have many original details remaining.
The tour is only $6 though, so if you have some extra time and are curious, check it out!
On your way to your next stop at the Old North Church, you’ll want to stop over on Hanover Street to pick up a cannoli from Mike’s Pastry.
Don’t be turned away by the crowds; squeeze your way in and up to the counter to order some of the best pastries in the North End! Once you get to the counter be prepared to order – the shopkeepers more QUICKLY and there is no real line, so first come first serve. Pay with cash if you can – it’ll make the process much quicker. My favorites are Oreo Cannoli, Chocolate Dipped Cannoli, and Hazelnut Cannoli.
And always opt for the extra powered sugar, of course! Cannoli not your thing? Mike’s is also known for their lobster tail pastry and other delicious homemade
confections!
Who serves the best North End's cannoli is actually a hotly contested matter. I am solidly on team Mike's Pastry (for reasons I will go into in another post soon) but if you're down for a taste test adventure, and possibly a stomachache, grab cannolis from Modern Pastry and Bova's as well. Let me know your thoughts in the comments below or tag me on Instagram (@graciegoes_blog)!
Once you have acquired your sweets, continue down Hanover Street towards the Old North Church. You’ll come to the Paul Revere Mall, which just so happens to be the perfect place to sit and enjoy your Mike’s treat!
The Mall connects through to the Old North Church, of “one if by land, and two if by sea..” Henry Wadsworth Longfellow lore and is very much worth a visit!
General Admission is $5 per person for a self-guided tour, and there are docents around to ask any questions you may have. If you have time however, I highly recommend taking one of the guided tours to see the bell tour or the crypts. These are $10 ea and include general admission to the sanctuary as well. Be sure to check out the Old North Church’s website and book in advance if you can!
This will be our last stop on the Freedom Trail. If you have more time another day, I recommend heading to Charlestown to climb the Bunker Hill Monument and see the USS Constitution. But if you don't make it out there don't worry, you've hit the best historical highlights of the city, in my opinion!
If you haven’t already ruined your appetite eating too many sweets or fallen over from the exhaustion of walking across the entire city, you’ll want to stay for dinner at one of the incredible authentic Italian restaurants in the North End. I’ve been to many and can honestly say I’ve had unbelievable meals each and every time.
These restaurants are all pretty small and fill up quickly, so I recommend making a reservation if you do not want to wait in line. Looking for something more casual? Grab a meatball pizza pie from Regina’s. Have a bigger group? Grab a reservation in advance at Carmelina’s. Assaggio, like so many others, has world class pasta and Ristorante Fiore has an open roof deck. Seriously, you can’t go wrong with any North End restaurant, and they are worth the wait!
Ristorante Fiore with their open roof
The line for Regina's can sometimes get long... some of the best pizza you'll ever have though!
My favorite is their meatball pizza.
And as you sit and reflect on your day, be sure to treat yourself to a glass of red wine for me. Cheers and welcome to Boston!
