For the first time since Roman was born nearly two years ago, my husband and I left Roman for a weekend away. We chose Boston, Massachusetts to visit. We’ve always wanted to go and we found great deals on flights using credit card points. This Boston itinerary is everything you need to know to spend an enjoyable getaway weekend in Boston.
Was it a little nerve racking leaving our kid behind for the first time? Yes. Was it absolutely needed and good for our marriage? Also yes!
It was so nice to spend time together without constantly being interrupted. We also need to be better about having more regular date nights at home lol. As much as I love traveling with kids, I encourage parents to take some time away and travel as a couple.
Whatever your reason for visiting Boston, this beautiful city is full of history and culture. I loved seeing the contrast of old buildings against the newer skyscrapers. And although Boston is the capital of Massachusetts and is definitely a major city, it doesn’t feel crowded or hectic like neighboring New York City. In fact the traffic was manageable, there weren’t lines in most places and the overall vibe was easygoing.
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Three Day Boston Itinerary
So here is a three day Boston itinerary based on our visit. With minor tweaks made based on what I learned during our trip. This itinerary should offer you the perfect weekend in Boston, especially if you are a first time visitor.
I felt like three days was a great amount of time to see a lot of the city. There is definitely more to see (we didn’t head over to Cambridge to see Harvard University or MIT this trip for example) but we did hit the top sights on my list and had a wonderful weekend in Boston.
Day 1: The Freedom Trail
Before you start sight-seeing for the day I recommend fueling up with a good hearty breakfast. This first day will have the most walking and a filling breakfast will start you off on the right foot. I recommend Tatte Bakery, the food was delicious and they have a location right next to the Boston Common, the first stop on the Freedom Trail.
The Freedom Trail is a collection of 16 key historical buildings, places and cemeteries that played an important part in the American Revolution and the founding of the city. You will follow a 2.5 mile brick trail through the city, some of the 16 stops are free to enter while others are now museums that require an entry fee.
I recommend starting at the visitors center where you can pick up a free map, ask questions as well as purchase guide books and souvenirs. We purchased a small guide book that was IMMENSELY helpful. It gave a small 2-3 paragraph explanation on each stop as well as its historical significance. If you are not booking a tour and going on a self-guided tour instead I recommend using some sort of guide book or audio tour.
The Visitors Center is in the Boston Commons, from there you can follow a literal red brick trail through the heart of Boston and its many historic landmarks. These are the 16 stops on the Freedom Trail.
Freedom Trail Stops
Boston Common: The Boston Common is a large plot of communal land that has been used for cow grazing, camping grounds for the Redcoats as well as a place of celebration. Today it is a large park where people can play, listen to concerts, ice skate and enjoy the outdoors. The Boston Common is the oldest city park in the United States and it is the perfect place to start a long weekend in Boston.
Massachusetts State House: The Massachusetts State House was originally built as a place for government officials to work and it is still used for this purpose today.
Park Street Church: Next is the Park Street Church, once the first landmark that travelers saw as they entered Boston. The church has a mission to support human rights and social justice and was known for supporting abolitionist causes.
Granary Burying Ground: The final resting place of John Hancock, Paul Revere, James Otis, Samuel Adams as well as Benjamin Franklin’s parents is here in the Granary Burying Ground.
King’s Chapel & King’s Chapel Burying Ground: A prominent Angelican church built in an area primarily occupied by Puritans. The graveyard next door was the first burying ground in Boston.
Boston Latin School Site & Benjamin Franklin Statue: Boston Latin is America’s oldest public school and boasts illustrious alumni such as Samual Adams and John Hancock. Benjamin Franklin was a notable student and high school dropout.
Old Corner Bookstore: This old bookstore and printing shop has printed the works of numerous famous writers. Today the large building is home to several businesses including Chipotle.
Old South Meeting House: It was here in this historic church building that the citizens of Boston attempted to find a solution to get the tea from England sent back since they lacked representation in a government that was taxing them. When no solution was found it is said that here in the Old South Meeting House Samuel Adams gave the secret signal to start the Boston Tea Party.
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Old State House: This 300 year old building can be found at the heart of many colonial events where the local government and citizens stood up for freedom and liberty. It was also here on the front steps of the Old State House in 1776 that the Declaration of Independence was first read in Boston.
Boston Massacre Site: The next stop is right in front of the Old State House. The site of the Boston Massacre is marked by a ring of cobblestones to remember the historic events that day.
Faneuil Hall: The hall has been home to successful shops on the first floor since it was built in 1742. Today you can shop in the Faneuil Hall marketplace at several cute local shops. The second floor meeting hall is even more important to the revolution as the location of several protests and inspirational speeches.
Paul Revere House: Paul Revere’s house dates back to the 1680’s and is Boston’s oldest building still in existence. Once the home to Paul Revere and his family it is now a museum you can walk through.
Old North Church (& Nearby Copy Shop): It was in the steeple of this church where Robert Newton with the help of Paul Revere hung lanterns to warn the patriots that the British were coming by boat.
Nearby, at the back of the church’s courtyard is a replica print shop that is worth a visit. A very dedicated man has recreated an era specific print shop where he prints duplicate documents such as the Declaration of Independence. You can purchase some of these replicas if you wish or you can just come in and watch a demonstration.
Copp’s Hill Burying Ground: This cemetery is the final resting place of many Bostonians and close to 1,000 free African-Americans. The area was also used by the British during the Battle of Bunker Hill because of its height.
USS Constitution: This ship has a storied and amazing past that has led it to several countries around the world and a well earned reputation. The USS Constitution is the oldest commissioned warship afloat in the world and is free to visit. You can walk through all three levels of the ship, a true amazing stop to visit.
Bunker Hill Monument: The Battle of Bunker Hill was the first major battle in the Revolutionary War. The monument memorializes the efforts of Colonials in a battle worth remembering.
Lunch, Dinner and Evening Time
The best place to stop for lunch is Quincy Market located behind Faneuil Hall (stop #11). The market has been turned into a ginormous food hall where you can try delicious foods from Boston favorites like lobster rolls and clam chowder to gelato and Chinese food. Every age group and taste bud preference should be able to find something here to eat.
Near Paul Revere’s House is a part of Boston called Little Italy. This would be a great place to grab lunch or dinner one day at one of the many Italian restaurants, especially if you like pasta or pizza. A must visit stop is Mike’s Pastry, this is a great place to grab a canolli for now or for later! The line is long but it moves quickly and is worth the wait. They only take cash so make sure you have some on you or you stop by an ATM.
Walking the Boston trail will most likely take up the majority of the day. For us, we visited in the winter and it took us from morning till sunset at 4:15 and we didn’t pay to enter any of the museums!
After such a busy, tiring day of walking grab some dinner and then either take it easy in your hotel. Or if you are feeling up to it, grab a show in the theatre district at the Wang Theatre or Boston Symphony Hall.
Day 2: Museums and Neighborhoods
To start off day two of the weekend in Boston, head over to Acorn Street. This is the most photographed street in all of America. It is picturesque with its cobblestone streets, gaslight turned electric lamp posts and beautiful doorways. Occasionally there is even an American flag flying which feels truly patriotic. Getting here early will allow you to grab pictures with great lighting and NO CROWDS. We went once in the morning and once at sunset, it was super crowded at sunset.
Once you’ve snapped a few pictures to your heart’s content, it is time for breakfast. About a ten minute walk away is a donut shop called Blackbird Donuts, I loved their classic blackbird donut. They also have a unique everything but the bagel seasoning donut that has cream cheese filling that was pretty good.
If you aren’t feeling donuts, Flour Cafe is a few doors down. It was really busy and was on my list to try, we didn’t make it on this weekend in Boston trip though.
The Libraries
After breakfast, head to the Mapparium inside the Mary Baker Eddy Library. This is a giant glass globe built in 1935 that you can walk inside it! Entry costs a mere $6 and includes a few other exhibits as well. The Mapparium is a large circular room that shows the world as it was in 1935. It is beautiful to see, pictures aren’t allowed inside though so you’ll have to experience it for yourself.
When you’re done here, head 10-15 minutes up the road to visit Copley Square. Here you’ll find the Boston Public Library as well as Trinity Church and many restaurants where you can grab something to eat for lunch. The library is a large and imposing building that is open to the public. They even offer free tours on Mondays, Thursdays and Fridays, you can find times on the Boston Public Library website.
For lunch we ate at Parish Cafe, they serve large sandwiches and salads with indoor and outdoor seating. I would absolutely recommend it.
For the afternoon let’s explore the Fenway Neighborhood. Here you’ll find the Fenway Park, home to the world renown Boston Red Sox. During baseball season you can grab tickets to a baseball game or you can take a tour of the field anytime of year. Nearby are two amazing museums the Isabella Stewart Gardner Museum and the Museum of Fine Arts. You can most likely fit one, maybe two of these activities in an afternoon. If you want to do all three then I would switch this to the morning of day three. Once you’re done grab dinner and turn in for the night. Tomorrow is day three and will be just as full and busy as the previous days.
Day Three: What is there to do in Boston?
Day three is a choose your own adventure day. There are so many fun and exciting things to do, there are several options that you can choose from that best fit your preferences.
After breakfast start your day with the Boston Skywalk. Or if you’re trying to do Boston on a budget then a great alternative is the Independence Wharf Building 14th floor observation deck. It is free to the public, you simply have to show ID at the front desk.
Next head over to the Boston Tea Party Ships and Museum then grab some lunch. After lunch you could head over to explore the Harvard Campus to see Harvard Yard, the MIT campus and eat at the popular Harvest restaurant.
If you are wanting to stick near downtown Boston then I recommend the New England Aquarium or, for a more unique experience and at the right time of the year, you can go on a whale watching cruise in the harbor! You could also get some shopping done or go photo op hunting near Washington St and Summer St. There are lots of stores including Primark which has a “hello Boston” mural. The nearby Brattle Bookshop is very cute and sells discount books outside and antique books inside.
When is the Best Time to Visit Boston
Sometimes you have limited say on when you can take a vacation. If you do get to choose then here are some things to consider when spending a weekend in Boston.
The summer is peak tourist season which means crowds along with higher temperatures. However you are far enough north that the temperatures can be manageable especially in early summer.
The fall is probably the best time to visit Boston as the temperature drops and you can see the beautiful fall foliage. The trees erupt into a rainbow of reds, oranges and yellows. It should not to be missed.
The winter gets chilly and windy but the city is still worth seeing, especially when it is all decked out for the holidays. Make sure you pack in warm layers including a coat, hat, gloves and wool socks. We visited Boston in November, right after Thanksgiving. It was chilly and windy at times but with layers I was still comfortable despite spending hours outside at a time.
The spring can be a beautiful time to visit with mild temps and lovely spring blossoms. However, it rains a lot so make sure you bring along an umbrella and a raincoat to avoid getting drenched while you’re out and about.
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How to get around Boston
Walking
Boston is a very walkable city and many of the sights are not too far from each other. Your best, and often quickest way to get around the city is going to be by walking. Make sure you bring along some comfortable shoes and you’ll be all set for a great sightseeing weekend in Boston.
Public Transport
For the sights that are too far apart to walk between or when your feet just need a break, the subway and bus system is your best bet. Nicknamed “the T”, the buses and subway are very easy to use. Plus google maps will include them in your navigation if you select transport in the menu.
Tourists can purchase a one day pass or a seven day pass called the Charlie Card for unlimited use of the subway and buses while you are on vacation. They don’t offer a three day pass but the seven day pass was less than $25 a person when we visited. Not to mention that kids 11 and younger ride for free. That was really worth it for a weekend in Boston when an Uber from the airport to our hotel alone would have cost us $45.
These passes can be purchased at most subway ticket kiosks. This includes kiosks found in the airport near baggage claim making it a very convenient mode of transportation.
Driving
Driving is more of a hassle than it is worth most of the time in Boston. Traffic can get congested due to confusing narrow streets and parking is really hard to find. Unless you are just visiting the city for the day or taking a day trip out of the city I would avoid renting a car.
Where to Stay in Boston
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Courtyard by Marriott: We stayed at the Courtyard by Marriott right across from the Wang Theatre. The location is unbeatable at this price point. Only a ten minute walk from the Boston Common we had easy access to all the best sights in the city. Plus a nearby subway station got us to any further sights we wanted to see.
Outside of the location the hotel was unremarkable. The rooms were small, there was not mini fridge, and breakfast was not included. One thing to note as well if you are driving a car was the extremely high parking fee per night. I would avoid staying here if you are bringing a car.
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Four Seasons: The Four Seasons is a gorgeous hotel and they are located right across the street from the Boston Commons. If you are looking for a splurge worthy place to stay during a getaway weekend in Boston then you can’t go wrong here.
What to Pack for Boston
First up, make sure you are packing comfortable walking shoes. There is a lot of walking to be done especially if you are walking the Freedom Trail while you are visiting. Bring a pair of cute tennis shoes, supportive sandals or warm boots in the winter but just make sure you can walk several miles in them and still be comfortable.
Beyond the right shoes, what you pack is going to largely depend on when you’re visiting. In the spring and fall make sure you bring a light jacket or two. In the fall and winter I would definitely pack all the cozy sweaters to wear. And in the winter, make sure you bring a hat and gloves especially for when you are outside most of the day.
Top Tips for a Fun Weekend in Boston
- Take the chance to walk around the city or use public transportation. Parking is an absolute nightmare so you’ll probably end up walking between sights anyway. Skip the car rental for this trip.
- The 7 day subway pass includes ferry transfers on the Charlestown Ferry. This can be a fun way to get out on the water and take a day trip somewhere new like Cape Town.
- Seafood is the food specialty of the area. You can find amazing dishes from oyster to lobster rolls to clam chowder just to name a few just about anywhere you go in the city. If you are a seafood lover make sure you get your fill of fresh caught and delicious meals here in Boston.
Practical Information for Boston, MA
Find accommodations, sign up for a local tour, or buy your Boston Travel Guide.
Weekend In Boston
There is so much to do, see and eat in Boston I know you’ll have a wonderful time! Make the most of your weekend in Boston by using this Boston itinerary as a guide for some of the best things to do and see. Make sure you tweak it to best fit your interests and the time you have to spend in the city though to really enjoy your trip.
The city of Boston is steeped in history both good and bad. Be sure to take some time to learn something new but also enjoy the beauty of the area and of course eat some good food. Is there anything I missed that you would add or change? Let me know below.
