The Amiable Traveler - A Three-Day, Must-See Itinerary to Boston
“My family and I are coming to Boston for three days? What would you recommend that we see and do? Where should we eat?” These are questions I have happily answered to individuals over and over again. And now I’ve put all your must-see Boston sights and experiences into one blog post. Here you will find all the best tips from my years of experience taking friends and family around Boston and exploring Boston on my own. This post will map out a three-day Boston itinerary that includes, what I will refer to as: Historic Boston, Beautiful Boston, and Delightful Boston.
“The Amiable Traveler Guides - Follow along with the Amiable Traveler Guides, if you, like me, enjoy pleasant travel with companionable people, the comfort of distinctive lodgings with thoughtful touches, seek out good baked goods and restaurants with quiet views, enjoy spending the day in nature but want a good meal and a comfortable bed at the end of it, like carefully curated shops run by cheerful shopkeepers, and like knowing the inside tips before you travel. Based in New England. Explore my day trip and getaway guides to the New England states. Exploring farther whenever possible!”
— Debbie Harpe, Wonderful Life Farm
Inside tips for following Boston’s Freedom Trail.
DAY 1 - DISCOVERING HISTORIC BOSTON
Boston is a fabulous walking city! So, get an early start (that’s an insider tip there), put on your most comfortable shoes (that’s an insider tip), wear a jacket or coat if necessary (that’s another insider tip), and get ready to experience the best historical sites in Boston by walking the Boston Freedom Trail. The 2.5-mile trail will seem much longer and take you a full day of exploring on foot. You will pass 17 historic sites important to the founding of the country. Today will be one of the best field trips you’ve ever taken! The trail is easy to follow, as it is denoted by a brick ribbon or a painted red stripe on the sidewalks and roads of Boston.
Follow the red line or red, brick line to walk the Freedom Trail.
Inside Tip: Here is my best tip learned from years of experience walking the Freedom Trail…start from the end and work your way back to the beginning. Normally, people start in Boston Common and walk to the Bunker Hill Monument. The problem with that is that everyone tends to spend a lot of time at the sites at the beginning. And the very last site, the Bunker Hill Monument, closes at 4:30 p.m., with the last entrance to climb up into the monument closing 30 minutes prior to that. It is, speaking from experience, disappointing for everyone to arrive at the last destination too late to experience it. To avoid this:
Park your car in the underground parking at the Boston Common Garage. (It’s literally underneath Boston Common.)
Exit the parking garage via staircase or elevator. At the top, you will be in Boston Common.
Walk toward the Park Street subway stop by using the tall, white church steeple of Park Street Church as a guide through the Common.
Just across from Park Street Church, you will find the Park Street subway station. Descend into the subway and take the OUTBOUND Green Line to North Station. (Subway tickets are inexpensive.) Here’s a link to the Boston subway system…learn more.
Once you’ve arrived at North Station, exit the subway onto the surface streets and navigate with your phone’s maps program to Bunker Hill Monument. Along the way, you will find yourself meeting up with the red line or brick stripe of the Freedom Trail.
Start your walk of the Freedom Trail at the Bunker Hill Monument.
The Bunker Hill Monument, to this early battle in the American Revolution, is a tall obelisk with a sweeping view of the city at the top. The strong-legged among your group will want to climb the 294 spiral steps to the top. Be sure to visit the visitor’s center adjacent to the base, as well. The visitor’s center across the street is good for a quick walk through and a handy place for restrooms.
From here, you will now work your way back to your car the whole rest of the day by walking the trail in reverse. Most sites along the trail are free. The cost of those that charge is minimal and always worth it.
From the Bunker Hill Monument, you will visit the U.S.S. Constitution (definitely worth a tour). And then you will head back across the bridge and begin to wind yourself through Boston’s Historic North End. As you head toward the Old North Church, don’t miss the tall, narrow house…just one room wide…known as The Skinny House (or the Spite House).
The North End experienced a 19th century influx of Irish immigrants to Boston. They first settled in this area before another influx of Italian immigrants arrived and stayed. The North End is full of historic architecture and Italian restaurants, and the aroma of garlic hangs deliciously in the air.
After touring the Old North Church, you will pass by the famous statue of Paul Revere.
You will definitely want to tour the Old North Church. It is an excellent example of a classic, New England church. And it is famous for its belfry, wherein hung the lantern lights that signaled Paul Revere on his midnight ride. If you are traveling with children, be sure they are acquainted with Paul Revere before coming to Boston, as it will help to bring history alive for them!
LISTEN, my children, and you shall hear
Of the midnight ride of Paul Revere,
On the eighteenth of April, in Seventy-five;
Hardly a man is now alive
Who remembers that famous day and year.He said to his friend, “If the British march
By land or sea from the town to-night,
Hang a lantern aloft in the belfry arch
Of the North Church tower as a signal light, —
One, if by land, and two, if by sea;
And I on the opposite shore will be,
Ready to ride and spread the alarm
Through every Middlesex village and farm,
For the country folk to be up and to arm.”…- The Midnight Ride of Paul Revere by Henry Wadsworth Longfellow
After touring the Old North Church and passing by the iconic statue of Paul Revere, you will be heading through a busy section of Italian restaurants and cafés. It will be very tempting to pop into one for a leisurely lunch. Do so, if you wish, but my advice is to press on today for a quicker lunch elsewhere and return to the North End for dinner at some point in your three days in Boston.
However, you will definitely want to deviate from the brick trail just a few steps to buy a cannoli (or two or three or seven) at Mike’s Pastry. It is a Boston institution and a must-do when you’re in the city! The line may be out the door and down the sidewalk, but it will move quickly, so don’t be deterred by it. Mike’s cannoli come in a myriad of flavors, all photographically displayed around the top of the walls inside this no-nonsense bakery, so you can decide what you want to order before you get to the front of the line. Note: Mike’s is CASH ONLY.
Definitely pay for a self-guided tour of the Paul Revere House.
From Mike’s Pastry, jump back onto the Freedom Trail and follow it to Paul Revere’s House. There is a charge for a self-guided tour of his home, but I highly recommend that you do this. You will learn about the man, his family, and his work, as well as touring an excellent example of colonial architecture. (You’ll appreciate knowing more about his work for Day #2 of touring Boston.) It does not take long to tour the house.
Leaving here, you will now start to make your way out of the North End, through the very nice Rose Kennedy Greenway with its gardens, fountains, and swings. This is a great place to sit and relax for a moment (especially if you can manage to nab a swing for a minute or two). You are now working your way back into the main part of Boston.
And you are probably starting to get hungry for lunch. You will pass historic taverns, but I advise you to grab a quick lunch at Quincy Market (also a stop on the Freedom Trail). Quincy Market, an early-19th century market for commerce, is now a giant food court. Everyone in your party should be able to find something they’d like to eat here, including New England classics like lobster rolls and clam chowder. There are usually street performers in the courtyard between Quincy Market and the next stop on the Trail, Faneuil Hall. It’s fun to sit on the steps and watch them perform while you eat your lunch. Inside tip: If you happen to be walking the Freedom Trail in the autumn, there are sometimes vendors selling hot nuts outside of Quincy Market…so delicious on a crisp day!
You will pass this historic tavern between the North End and Quincy Market along the Freedom Trail.
This Redcoat always makes for a great photo opportunity.
After lunch, just pop across the courtyard into Faneuil Hall. It is run by the National Park Service. You’ll want to listen to their informative presentation. It doesn’t take long, and you’ll learn all about the history of this famous building and the orators who have spoken here.
The remainder of the Freedom Trail will pass by the Old State House, the Old South Meeting House (where the British housed horses!), two graveyards, and the Massachusetts State House (with its gold rotunda) before you end back where you started…at Boston Common! I definitely recommend you pay the nominal fee and tour the Old South Meeting House. And be sure to allow time to wander in the Granary Burying Ground, where you can read the inscriptions on the headstones and see the graves of Boston’s famous citizens.
Visit the graveyards in Boston and find the headstones of its famous citizens, like Paul Revere.
It’s hard to believe that you’ve walked all day and only covered 2.5 miles, isn’t it? But you’ve seen great spots in the city. Time to turn in for an early night and rest those feet. Tomorrow will be less walking.
DAY 2 - DISCOVERING BEAUTIFUL BOSTON
While yesterday, you did miles of walking and saw much of the city, today you will confine yourself to one building. But it’s going to be amazing! Today, you will spend the day touring the Museum of Fine Arts. This is a world-class museum containing art from ancient to modern, with a particularly excellent American Art wing.
The Museum of Fine Arts in Boston is a great, all-day experience.
You can get to the Museum of Fine Arts by car or subway. If you are driving, there is a parking structure for the MFA a short walk from the entrance. If you taking the subway, from the center of Boston, you will want to take an OUTBOUND GREEN line whose subway car is marked “E”. All those details are very important, because only a green “E” train will get you there. Hop off at the Museum of Fine Arts exit and walk across the street to the museum. (To return, you will need to catch an INBOUND train at the same stop.)
Just a note: If you have three days in Boston and one of them is rainy, that might be a good day to spend at the MFA.
The entirety of the Museum of Fine Arts is difficult to see in one day. I suggest discussing among your party if there are any galleries you do not wish to see and eliminating those from your day. My personal list of must-see galleries for a first-time visitor to the MFA would include: American, European, Ancient, the Musical Instrument Room (a small gem of a collection), and the main staircase and rotunda murals. Don’t miss the Revere silver (made by both Paul Revere and his father) in the American Art wing. And I always enjoy the John Singer Sargent paintings in the American wing (being acquainted with his works will be beneficial for tomorrow’s touring.)
This large painting of George Washington can be found in the American Art wing of the MFA.
There are several places to eat in the MFA, but if you are optimizing time and want to economize, I suggest you head to the basement cafeteria. Here you will find a wide-range of quick, grab-and-go options to please everyone. There’s seating within the cafeteria or in the adjacent courtyard (open seasonally). There are also bathrooms on this level.
Visit at least one of the MFA’s excellent gift shops before you leave. Postcards of their favorite works of art are always a simple, compact (easy to pack), economical souvenir for kids.
If you have any energy leftover and want to see still more art, you can walk a couple of blocks to the Isabella Stewart Gardner Museum. If I had to choose between the two, I’d do the Museum of Fine Arts. But I have managed to squeeze both into one day. It houses an extensive art collection spread over three stories in Isabella Stewart Gardner’s home, centered around a soaring courtyard alive with lush plants (making it a haven in the city in the dead of winter). The Isabella Stewart Gardner is famous for experiencing, unfortunately, the largest art heist in world history. The empty spaces, frames still intact, are there for all to see…just waiting for the return of the priceless works.
I hope you’ve enjoyed viewing the most priceless beauty of Boston today with your tour of the Museum of Fine Arts.
DAY 3 - DISCOVERING DELIGHTFUL BOSTON
Your first day of touring gave you a taste of the richness of the city’s history. Your second day immersed you in the beauty of its art. Today is going to be all about falling in love with Boston. If this is the very last day you have in the city, you will be sad to leave at the end of it. It is a day of delights! Insider tips: get an early start, wear comfortable shoes, and bring an appetite!
I recommend that you park your car in the Boston Common Garage, as you did the first day. Exit the parking structure up into Boston Common. Spend a moment to orient yourself. On one side, you’ll find busy Charles Street that runs between Boston Common and The Public Garden. And on another side, you’ll see a long row of brick buildings with shutters, balconies, and fabulous, historic architecture.
That is Beacon Hill, Boston’s oldest neighborhood and where the day starts. Find the intersection of Charles Street and Beacon Street, at one corner of the Common. Cross Beacon Street and wander up Charles Street into the shopping area of Beacon Hill. Resist the urge to stop at Starbucks on the corner (you can go to Starbucks anywhere), and instead head up a few blocks to the intersection of Mt. Vernon and Charles Street and stop in at Tatte (rhymes with latte), where the locals go for “elegant comfort food”…morning breakfast, bakery treats, and lattes. If you happen to be there at lunchtime, I highly recommend the shakshuka.
From Tatte, cross Charles Street and continue in the direction you’ve been traveling up Charles Street to find Beacon Hill Books & Café. This exquisitely curated book shop will have your heart! No detail has been left undone in the interior design of this four-story gem. It is, quite possibly, the most lovingly curated spot in the city. Don’t miss the children’s book department, which encompasses the entire third floor with so many charming details. The basement houses its fine café, where you are wise to have a reservation (booked far in advance). But always ask, there just might be a table for you.
The cozy interior of Beacon Hill Books & Cafe welcomes you in and suggests you stay for a while.
After a thoroughly delightful visit there, exit the door and turn right and proceed up Charles Street to the following intersection, Pinckney Street, and turn right. In about a block, you will come to Rouvalis Flowers, the prettiest little flower shop with an ever-changing curbside display of botanical beauty. Pop inside and pick up one of their signature scented candles as a souvenir of your time in Beacon Hill.
Rouvalis’ storefront is beautiful in whichever season you visit Boston.
Now, you’re just going to wander to your heart’s content the quaint neighborhoods of Beacon Hill. The architecture is some of the prettiest and most charming in the whole of Boston. I love the little details…the window boxes and door knockers, especially. Inside tip: watch for historic markers on homes to learn more. The low doors that you find were once used as servants’ entrances. Use your phone’s maps feature to find Louisburg Square, a small private park with very fine architecture surrounding. If you’re in Louisburg Square in the springtime, you might find the famous, wisteria-covered house in full bloom. And if you’re there near Halloween, there’s one particular house that is over-the-top spectacular! I won’t attempt to tell you which one…it will be obvious. Also in Beacon Hill is the home used in the original Thomas Crown Affair movie with Steve McQueen. It is the last, free-standing home in Beacon Hill. And don’t miss Acorn Street (use your phone’s maps feature). This cobblestone street, a private lane, is one of the most photographed streets in the world.
Take time to enjoy the beautiful area of Beacon Hill, Boston’s oldest neighborhood.
Retrace your steps or find your way back to Charles Street to leave Beacon Hill. You will walk back down Charles Street and cross Beacon Street again, but this time (instead of going to Boston Common) you will cross into the corner entrance of The Public Garden, the first botanical garden in America (est. 1837). Within a few short steps, you will encounter the Make Way for Ducklings statue…the ducks made famous in Robert McCloskey’s children’s book Make Way for Ducklings. (If your children are not familiar with it, do read it before coming to Boston. It’s a classic!) In the springtime, the duck statues wear Easter bonnets. And sometimes they sport Patriots’ jerseys. Boston is a city with a sense of humor!
Wander towards the pond and up onto the bridge. If you’re in Boston in the summertime, the swan boats will be out and you can take a ride on them (for a small fee). It’s an iconic thing to do in Boston, especially if you’re visiting with children.
From here, continue crossing the bridge and heading towards the statue of George Washington mounted on his horse. Pause to admire the seasonally-changing plantings in The Public Garden…always beautiful! Take a photo with the George Washington statue…a Boston classic. Then exit The Public Garden at the gate by the statue. You will be looking straight across at a tree-lined avenue. You are now going to spend the rest of the day in the area of Boston known as the Back Bay, one of my favorite parts of the city.
The tree-lined street is Commonwealth Avenue and is one of the prettiest strolls in the city. Stroll down the middle, beneath the trees and see the statues of famous citizens. This stroll is particularly beautiful near Christmas and into January, when the trees are lit with Christmas lights and walking beneath them is simply magical! Walk as far as Clarendon Street and turn left.
By now, you’ll probably be pretty hungry and need a delicious, quick, healthy, and economical place for lunch. Walk a few blocks on Clarendon Street (passing by that charming chocolate shop…it comes later) until you get to very busy Boylston Street and turn right. Just a few doors down, you will find Dig, our favorite spot in the city for lunch! They offer salad and grain bowls with a myriad of choose-your-own additions. You can eat there, or take your lunch to go. If you take it to go, I recommend continuing to walk down Boyslton Street to the next corner, where you will cross Boylston and enter the Boston Public Library. Find their interior courtyard and eat your lunch in its peace, quiet, and lovely beauty.
Plan to spend at least an hour at the Boston Public Library.
Conveniently, the Boston Public Library is the next stop on this day of touring, so if you’re eating there, you’re in the right place. It is far more than a library. It is, in many ways, a mini-art museum. The bronze doors you opened when you walked in were carved by Daniel Chester French, who carved the Lincoln Memorial in Washington D.C. and the Minute Man statue in Concord, MA. I highly recommend you use the Art and Architecture Tour information on their website, available here, to learn more about what you’re seeing as you tour the library. Walk up the grand staircase and find the reading room.
Enjoy the quiet grandeur of the reading room at the Boston Public Library.
From there, wander into the Abbey Room and marvel at the wall murals depicting Sir Galahad and the quest for the Holy Grail. There should be laminated cards (housed in this room) that you can use to read more about the murals.
Then find your way up to the next story to view the history of religion wall murals by John Singer Sargent (some of whose other works you would’ve seen yesterday at the MFA). Again, there should be laminated papers available explaining what you are seeing in this room.
Exiting the Public Library, return to Boylston Street and continue on in the same direction. Before you have even passed by the entire outside of the Public Library, you will find the finish line for the Boston Marathon. It’s a stripe that runs across Boylston. It’s a great photo opp for any runners in your family.
Passing that, continue on for a few blocks until you get to the Prudential Center, which is a large shopping mall. The Prudential Center is an easy to spot landmark in the city for its pointy antenna tower on the top of a very tall building. I might not normally put a shopping mall in a travel guide, but the Prudential Center stands out to me for three reasons: Läderach (a Swiss chocolatier) where I recommend their dark chocolate-blackberry bark, Eataly a wonderland of Italian food (restaurant dining, grab-and-go, gelato, and a market), and View Boston for an unsurpassed, rooftop view of Boston. View Boston is new (opening in 2023), and I have not personally experienced it. However, there used to be a restaurant where it is, and I have dined there, so can vouch that the views from the top are truly spectacular. Look into advance reservations for View Boston (fees apply).
Exiting the Prudential Center, cross Boylston and walk up any side street to Newbury Street, a major shopping district in Boston. You are now working your way back to your car. Stroll down Newbury Street until you get to Clarendon and turn right, where you will end your day in the sweetest, possible way…at my favorite chocolate shop…L.A. Burdick Handmade Chocolates. It is located in a charming, little house in the midst of tall buildings. You can’t miss it! And I must say that it never looks more enchanting than when it’s snowing in the city.
L.A. Burdick sells handmade chocolates, pastries, cookies, coffee, and hot chocolate.
My daughter, and frequent Boston travel buddy.
It’s a great place to pick up a box of chocolates (including their signature chocolate mice) to take home to someone special. But the real star of the show here is their hot chocolate! The hot chocolate at L.A. Burdick is widely considered the best in Boston, and it never disappoints. If you’re coming in the summertime, order an iced hot chocolate. My go-to order is: one, small hot chocolate half milk-half dark and one chocolate-raspberry cookie (quite possibly the best cookie on the planet).
Exiting L.A. Burdick, turn left to return to the tree-lined Commonwealth Avenue to return to your car. Alternatively, you can continue down Newbury Street with its high-end shops at this end. It’s always beautiful to stroll through the Ralph Lauren store. Either route will return you to The Public Garden, which you will cross to return to Boston Common and your car.
A few other random recommendations in Boston are:
Walk along the Esplanade and the Charles River on the back side of Beacon Hill.
Visit Fenway Park. Grab burgers at nearby Wahlburgers.
Near the Prudential Center, enjoy really good ramen at Hokkaido Ramen Santouka Back Bay.
Enjoy gourmet pizza and excellent pasta at Figs in Beacon Hill.
I’m not a big donut person, but I’d walk a couple of miles for Kane’s Donuts. They are a cut above! Don’t miss the crème brûlée donut, the Boston cream (obligatory in the city), and the raised chocolate frosted (which is so simple, but so monstrously better than anywhere else).
I hope you found this travel guide thoroughly inspiring and incredibly useful for making great memories on your next trip to Boston! See you in the city! Here’s a handy image to pin to your travel or New England boards:
