Boston is probably my favorite city I have visited! The architecture, food, contrast of old and new, and the beauty of such an old city captivates me. Boston during fall is beautiful with all the leaves changing colors and the cool crisp air. But how do you see Boston in one day?! Let me tell you how we did it!
During a trip to see my grandma in Massachusetts, I knew we had to find a day to visit Beantown! B and I had been trying to find a time to visit my grandma for a few months. He had never seen her cute little house on a pond. Plus, I had never been to “Boston in the fall!” So during our 5 days off in November, we decided to go for it and plan our trip!
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When trying to plan a trip, I always start with a search for plane tickets. Finding the best deals and the cheapest tickets is imperative! Usually, if I cannot find cheap plane tickets, we change our location and go somewhere else. I had already been searching for a couple of days and found that the tickets were sooo expensive. B and I could not pay $300 round trip per person. It just wasn’t going to happen.
During my research, I found a website called Skyscanner! Click this link to see the website –> Compare airlines, dates and prices all in one place with Skyscanner. It shows you the cheapest flights with tons of airlines for multiple search dates. When I searched flights on Skyscanner, I found super cheap flights to Boston from Southern California. I’m talking less than $100 per person round trip!
These tickets were so cheap, that I told my parent to come with us. My mom had been wanting to go see her mom for a while. So we made it happen! All 4 of us got on a plane and headed to Boston.
Most of our time in Massachusetts was spent up on the border close to New Hampshire. My grandma lives in a tiny town up there, a little over an hour away from Boston. Out of the 5 days we were there, we took only 24 hours to wander around Boston. 24 hours is a short amount of time, but we were going to see as much as possible.
Our Boston Day Trip
FIRST STOP: DUNKIN DONUTS….DUH
Anytime you are on the East Coast doing anything, get Dunkin Donuts! (I am so happy they now have one 2 miles from my house!) But really. Their coffee is amazing and kept us awake and energized for our day. So we took off driving into Boston and I was drooling over the colors still on the trees. Thankfully, there were still a lot of colorful trees. Usually the week before Thanksgiving doesn’t have much in way of color from what I was told. However, we still had lots of pretty trees to look at!
SECOND STOP: BOSTON! BEACON HILL
Arriving in Boston, we headed first to Beacon Hill next to the Boston Common and Public Garden. Our first stop included pretty difficult parking even for a week day. However, we parked next to a fancy looking Starbucks, and got out to walk around. The streets were beautiful! The buildings and front doors were so colorful.
We walked leisurely up and down the streets to soak in all the gorgeous architecture.
One street in particular is a MUST SEE. It’s one of the only real cobblestone streets left. (They are actually taking them out because of the damage it does on people’s cars.) The street is Acorn Street See the picture below.
It’s an extremely popular street to walk down. And let me tell you, walking down cobblestone streets is super romantic, but SUPER difficult! Haha!
Even in November, you can still find some extremely colorful trees in Boston.
THIRD STOP: PUBLIC GARDEN AND LUNCH
All of that walking around Beacon Hill made us hungry for lunch. While we were walking, we found an awesome pizza place that I would highly recommend to anyone in the Boston Common area. It’s called Upper Crust Pizzeria, and we took their mouth-watering pizza to a park bench in Public Garden. Public Garden is right next to Boston Common, and there is a gorgeous walking path with tons of trees to admire and animals to watch.
FOURTH STOP: BOSTON COMMON AND FREEDOM TRAIL
Once we had finished our fantastic pizza, we headed across the walkway to Boston Common.
Boston Common is a huge beautiful park right below Beacon Hill on a map. It is also the start of the Freedom Trail! We walked across the park to the beginning of the Freedom Trail and found the visitors center. We got a map and started off! Boston Common is actually the first stop on the Freedom Trail. In the park itself there are a couple of things to stop and see. Then you cross the street and off you go. If you want to read specifics about the Freedom Trail, read this post!
Here are the stops you will see along the Freedom Trail:
- Massachusetts State House
- Park Street Church
- Granary Burying Ground
- King’s Chapel
- Site of the First Public School
- Old Corner Book Store Building
- The Old South Meeting House
- Old State House Museum
- Boston Massacre Site
- Faneuil Hall (Quincy Market behind)
- We did stop at Quincy Market! We had to see all the shops, and of course the Cheer’s sign in Faneuil Hall!
- Paul Revere House
- Paul Revere Mall
- Old North Church
- USS Constitution (a ship)
- Bunker Hill Monument and Museum
We did not venture to the USS Constitution or Bunker Hill. It would be a lot more walking, and we had reached our stop in Boston’s North End. Because it was November, it was getting dark at around 4pm and we were getting hungry. The Freedom Trail is a lot of walking!
FIFTH STOP: NORTH END
The North End of Boston is considered the Italian quarters. You can tell because of the plethora of amazing Italian food smells coming from everywhere! For dinner, we picked Giacomo’s Ristorante. Click the link to find out about it and see the menu! This restaurant in the North End opens at 4:30pm Monday through Thursday and is first-come first-served. I was warned that a line starts at the door sometimes by 4pm! By convenient timing, we got to the restaurant just a little after 4 and plopped down on the sidewalk to rest in line. However, there were already 3 people in front of us!
Once the doors opened, the hostess seated us in a tiny and very cute literal hole in the wall. Let me preface by saying it is TINY! But aren’t those usually the best places? I can tell you that this was literally the best homemade Italian food I have EVER eaten! Also, the price was extremely reasonable! Which means we didn’t break the bank in order to get authentic food. If you have a chance, order the lobster ravioli with diced tomatoes in garlic creme sauce.
After the first bite, I knew I had died and gone to Heaven! Other food that was ordered for our party was fried calamari, fettuccine with sun-dried tomatoes, and chicken parmigiana. We all took turns tasting and I can say that all the food was delicious!
After we were completely full with homemade Italian food, we had to get a cannoli! Across the street a little was a fantastic bakery named Mike’s Pastry North End. Of course, we had to try multiple flavors!
Once we had our fill of sweets, we walked back to our car that we parked under Boston Common. It was so nice to walk the streets at night. Boston is such a beautiful city no matter what time you’re walking around. Because it was November, it was already dark. So, we ended our day after dinner and dessert. I know there are a bunch of things that you can do after dark in Boston, but unfortunately we did not have the time or energy. But hopefully this will give you a guide if you only have 24 hours to spend in Boston.
Serioulsy though, if you haven’t tried Skyscanner, click this link to download the app. It has saved me so much money on flight and rental car deals! Try it out!
Has anyone else tried to see Boston in a day? What are your suggestions?