Top Food and Activities for Your First Trip to Boston

So we stayed in the Beacon Hill Area. From the airport we could take the Silverline which was free and it dropped us off at the last location which was South Station. We were a few hours early to check into our AirBnB so we walked around to see the area. It actually turned out to be about a 25 minute walk right to where we were staying and was pretty straightforward.

And right between both locations was the Boston Common Park.

This is actually where the Freedom Trail starts too so you’ll want to check it out no matter what.

We also ended up going through the Public Gardens which is just the east part of the park that has a street going through it.

This has a little lake/pond, a bridge, fountain and a lot of other great picture locations.

On top of us being there for the PERFECT tulip bloom. They had so many little gardens full of different colored tulips.

The original bar the show was designed after closed down, so this is just a remake of it. They do have a better set up or example of the set upstairs that you can look at, but it’s just a bar honestly with Cheers merch.

If you’re a big fan or even just want to check it out for yourself, then do it! I’m glad we went just to cross it off my bucket list, but it won’t be something I go back for.

We love coffee and trying local spots, so when planning our next day, finding this close to our route was perfect.

It’s a lot “fancier” than we’re used to. As in there was a flavored espresso shot and we thought it was like an Americano or latte. So asking for an espresso shot over ice got us a weird look but that’s ok!

We ended up adding more water to it later and it was perfect. Just good coffee and it was super busy too but we didn’t have to wait long for our drinks.

Heads up, this will take most of your day, even if you don’t do the tour. You’re going to be covering a few miles walking all through Beacon Hill, a bit of Downtown, the North End and up towards Bunker Hill.

Bring water and plan to stop for food along the way.

With that being said, this is a must do! We didn’t do the tour but grabbed the $3 map from the Visitors Center and had no problem getting around. There’s actually a brick trail that takes you the whole way, and it’s just following along on that.

The map tells you what historical markers are coming up, you can stop at any of them along the way and then keep going.

I’d also recommend Googling the route and seeing if there’s any restaurants or other locations you want to stop at along the way. This would help you plan out food so you aren’t stopped on the sidewalk searching like we were for far too long.

I saw this cafe on one of our walks and it looked super cute I wanted to be sure we stopped in. Turns out there are A LOT of them throughout the area, and there was one actually just off the Freedom Trail near the end.

It was the perfect pit stop for a pick-me-up coffee.

I would’ve loved to try their deserts or food, but we were too full from another meal to try anything.

Could tell it’s a great place to stop after work or to start the weekend. My boyfriend even picked up a sweatshirt there because it was starting to get cold and I’m a bit jealous I didn’t get one too.

Their merch is great!

Once we were seated we both ordered the clam chowder cups and it was the perfect amount of food. And SO good! They had a lot of great options but this was delicious and a great way to end the day.

The walk back wasn’t bad either at night. We stayed in pretty safe areas and had no one try to stop us the whole time.

Then heading upstairs to look at the books only made my TBR list grow! I didn’t want to spend all my money and extra bag space on books, but we did end up going back to get one.

I picked the Boston Lioness which is by a local author. I haven’t started it yet but be sure to check out my book recommendations for when I have!

There are churches everywhere in Boston, and it’s crazy to see them next to modern skyscrapers. This was a really cool church with lots of history and detail that you don’t see in the small town churches.

We ended up going on a Friday, and that’s when they have an Organ concert! They don’t do guided tours on Friday because the performer is practicing before the noon performance so we did the audio tour.

It was cool to do, but we couldn’t hear much of it at all since they were practicing. I’m not super mad though because we didn’t stay for the performance but it was so incredible to hear the giant organ playing.

If you’re interested in going and can make Friday work, I’d definitely recommend doing it!

Did we end up at a college bar in our 30’s where it was shoulder-to-shoulder people because 2 nice girls outside the game told us that was a better bar for 30 year olds? Yes.

But it was still a great time! I’m not a huge sports person, but I wouldn’t mind going to another game if one was happening when we visit again. Compared to our home state field, it’s super nostalgic and was fun to see an older baseball field with history.

We obviously got hot dogs too but the line got super long. We even split up so one of us grabbed more drinks while the other got food, and we still had to wait awhile to meet up again. We could’ve waited for people to come around with them, but we waited too long and by that time wanted more beer that they didn’t have with the people walking around.

We also got to just how much distance we covered over the days too by finding all the stops we made. It also made it very clear we made the right choice not trying to walk to MIT or Harvard from the Beacon Hill area.

So if you’re looking for a place to kill time and like to see everything, Paramount View is a good place to see.

I will say, this was a second choice as the first choice was about a mile away and it was starting to rain when we headed out for dinner. It was close, like maybe 2 blocks from where we were staying, but we’re so glad we went!

It’s super small and intimate, and feels like it’s a bunch of Italian family members working together. The food was super good and comforting, and you got a good portion for the price.

We could’ve easily split our meal since my boyfriend and I both got the carbonara, but it was a nice snack for later.

We also grabbed a cannoli to go and that was amazing! Really simple compared to Mike’s and more traditional, but still really good.

We even heard some locals say this was a great spot to stop at and wish they had sooner since it’s close by.

It’s also not super fancy so we felt comfortable in our travel clothes of jeans and sweatshirt, not under dressed.

I didn’t grab any pictures because we were just enjoying the conversation and, in all honesty, were pretty tired our last night.