There is so much to see and do in Boston, Massachusetts. Heading down the coast from Maine to Rhode Island, I stopped into this coastal city to play tourist and sight-see. It’s full of history and perfect for those who want a good mix of tourist stops and coastal views. It definitely still feels like a city, as you are surrounded by historic buildings and new skyscrapers—but it’s right on the water too: a perfect mix for any tourist and for solo female travel.
I only had a day to explore the town, so I squeezed in many attractions quickly. If you're looking for a more in-depth guide full of hidden gems and things you do not want to miss, check out my ULTIMATE BOSTON TRAVEL GUIDE. Only have a day to spend in the city? This ONE DAY ITINERARY is for you.
MY TOP 10: There are many things to see in Boston, but if I could help narrow it down for you, here is my TOP TEN list. These highlights are not in a particular order, but without a doubt, the top of the list would have to include walking the Freedom Trail and visiting the restaurant where Cheers was filmed. Get ready to dive in -- you won't want to miss these top ten things to do and see in Boston, Massachusetts!
1. FREEDOM TRAIL. This is a 2.5 mile urban hike through downtown Boston. It starts in the Boston Commons area and works it way across the Charlestown bridge to the USS Constitution ship (aka, Old Ironsides) and the Battle of Bunker Hill Museum. If you only have time to do one thing, walk this trail. In fact, if you can walk it, you could skip any and all tours and see a nice picture of Boston for free. Truthfully, if you like to stop and take in the history, this could take your entire day. There are 16 stops along the trail, and each of them are worth the visit.
Download the .pdf of the Freedom Trail from the Freedom Trail Foundation here. The 16 stops on the trail are as follows: Boston Commons, the Massachusetts State House, Park Street Church, Granary Burial Grounds, King's Chapel & Burying Grounds, Boston Latin School + Benjamin Franklin statue, Old Corner Bookstore, Old South Meeting House, Old State House, Boston Massacre Site, Faneuil Hall, Paul Revere House, Old North Church, Copp's Hill Burying Ground, USS Constitution, and the Bunker Hill Monument.
What I loved about this trail is that it is clearly marked on the sidewalks with red brick. Once I began the trail, I did not need to spend time looking at my phone trying to find the directions to the next historic stop. I was able to look around me without worrying which way to go, as I was just following the red brick path around town. Just in case you want to skip a few of the sites or see what else is around you, save the below map for your reference.
2. BOSTON HARBORWALK:
This path is also marked. It takes you down by all of the cruise ships, as well as a few restaurants and ocean-front parks. This is a perfect place to watch people, relax after dinner or enjoy not being surrounded by huge buildings. After spending a few hours among all of the tourists in a busy city, I found the ocean breeze and watching the boats come in by the Harbor walk the perfect way to end my day.
If you are struggling to find the starting point, look for the check-in for Boston Harbor Cruises or The Chart House.
2. HOP-ON/HOP OFF TROLLEY TOUR
I am a huge fan of these live narrated trolley tours. Any town that I visit that has one, I purchase a ticket! I have never been disappointed, and it’s a perfect way to spend $45 because you get a tour plus transportation. Trust me: you do not want to try to drive your car around Boston, as there is lots of traffic and it costs money each place you stop.
Boston is definitely a walkable city, but just know that it is also very spread out. If you’re wanting to see everything, this extra transportation is so nice. Most parking lots I encountered were $20, so your bill would easily add up if you want to explore. Why not get a little history and tips while letting Old Towne Trolley navigate traffic for you?
There are two trolleys in town: Old Towne Trolley and City View Trolley Tours . I had traveled with Old Town Trolley in Nashville, Savannah and Saint Augustine and felt their company always came with a good reputation—so I went with them. The other company in town is about $10-$15 cheaper, but they do not stop at as many locations or cover as much ground.
TIP: If you buy a ticket with Old Towne, they give you 50% off an hour long harbor cruise making this additional tour only $20.
You can find their hub located not too far from Quincy Market or Faneuil Hall—two places you should totally explore. If you want to ride the bus from start to finish, it takes about two hours to complete the entire tour. If you have the time, I always ride through the city once and make notes of which stops I want to visit, as it helps me plan my day; however, if are short on time, hop off and visit the sites you encounter along the way. There are buses that come every 10 to 15 minutes and pick you up exactly where you got off. The last bus runs the route at 5:00, so you will have until about 6:00 to explore the last stops of the tour.
4. HANOVER STREET
I absolutely love seafood and tend to only eat seafood when I travel to coastal towns; however, trust me: you want to get Italian food in Boston. You will find tons of restaurants and food options on Hanover Street. Those Italian roots are strong in Boston, and you cannot go wrong with any restaurant choice.
Not hungry? Just walk down this street. It is definitely a sight to see! It will probably be very crowded and remind you a bit of New York—but it’s something you need to check out.
THE CANNOLI DEBATE: There is also a debate with all Boston folks of who makes the best cannoli in town. Why not decide for yourself!? You will find all three shops located near Hanover: Mike’s Pasty, Bova’s and Modern Pastry.
NOTE: The freedom trail runs through Hanover Street, so if you are walking this path, you will actually take Hanover to see Paul Revere‘s house. The Old North Church is also off of Hanover on your left. There is also a smaller parish called Saint Leonards that stayed open past dark and allows people to go inside. They have a peace garden that seems like a respite in the middle of a busy street. You’ll get to see all three of these highlights if you decide to check out Hanover Street—perfect if you are short on time.
5. BOSTON PUBLIC LIBRARY
When I was researching this town and discovered that people suggested I stop at the Boston Public library, I doubted their wisdom. Knowing I was short on time, I did not want to stop somewhere that was not going to be worth it. On a whim, I took their wisdom and WOW. It was the highlight of Boston for me! Do not skip this historical spot. It is a public building that closes at 5:00. So you will actually encounter tons of tourists trying to escape the heat and enjoying the air condition to people who actually live in town and are studying within the halls. There is a gorgeous outdoor pavilion on the first floor with a fountain in the middle. You also have to go up to the second floor and check out Bates Hall. The marble staircase with two huge lions flanking the stairs paired with the chandeliers makes it feel more like a church than a library.
6. TRINITY CHURCH Trinity Church is actually across the street from the library. Their schedule to tour inside the building does fluctuate depending on weddings and church services, but most days, you can get inside before 4:30. I missed it by 10 minutes! However, walking around the building, peering through the courtyards and taking in the massive doors and detailed art on the outside of the church left me in awe. Even if you can't get inside, walk the perimeter. I even saw a wedding party taking pictures on the lawn because it truly is that beautiful! It seems so very odd to have an old gothic-style building surrounded by huge new skyscrapers in the middle of town. It's something you have to see for yourself!
7. PAUL REVERE'S HOUSE Paul Revere's House is tucked in between buildings and cobbled streets. It would be easy to miss, but it's gray wooden exterior gives it away. It is a museum and national park, so you can go inside -- but know that most (if not all) buildings close at 5:00. Interestingly enough, Paul and his first wife had 8 kids. They moved into that house after their fifth child was born. After his first wife died, he married again -- and guess what? They had another eight kids. I had to see the house that held this large of a family!! Sadly, only eleven of the sixteen children made it to adulthood and of those eleven, only five outlived their father, Paul Revere.
Paul Revere's house is the oldest residential building that is still standing in downtown Boston. Lots of history here -- and if you only have time to do a few spots on the freedom trail, make this one of them!
8. CHEERS RESTAURANT I am the gal who has seen every Cheers episode! I am a huge fan of Ted Danson and Shelley Long and watching this old tv show, I feel in love with all of these characters who spent their spare time at this bar in downtown Boston.
You can go inside this bar and crazy enough, it looks exactly like the show. The front entrance is the same, as you go down into the bottom of the building. You can't help but think "NORM!" as soon as that front door swings open. Head up to the third floor to see the actual bar from the set where the majority of the show was filmed. You can even sit in the designated character's spots around the bar. I sat where Frasier sat and sipped a cold Coca-Cola -- geeking out and grinning from ear to ear. You have to make this special stop! BONUS: You can get a nice quality souvenir cup for $12 to bring back home -- and I did!! This is, no doubt, a tourist stop and certainly not off the beaten path, but if you are going to fight the crowds, this one is worth it. It was the highlight of my time in Boston!
9. OLD NORTH CHURCH One if by land, two if by sea. To this day, I still remember memorizing this poem as child that foretold the story of Paul Revere and what began the American Revolution. Informed by Paul Revere, the sexton of this church climbed the tall steeple tower to hang two visible lanterns to alert that the British were marching by sea, not by land. This church holds so much history, and the steeple itself is massive. Inside the church, it has unique pew boxes. This spot is a highlight on the Freedom Trail and is one of the most visited historical sites. The church is also the oldest surviving church building in Boston. You can catch this amazing statue of Paul Revere with the church steeple in the background as you leave Hanover Street and make your way to the church.
10. Boston Common & Faneuil Hall. Boston Commons is the oldest public park in Boston. When you visit this park, you can see the Massachusetts State House in the background. Within this park, many pirates, murderers and witches were hung from 'the Great Elm' tree (now gone), as well as Mary Dryer and three other Quakers who were standing up for their beliefs. It's also the site where over 1,000 British redcoats made camp during the British occupation of Boston in 1775. Just down the street, you can walk to Faneuil Hall where America's first town meeting was held.
There is so much history here. I hope you get out and explore! YOUR ADVENTURE AWAITS.
