My boyfriend and I just went on our first trip to Boston this spring and it might just be our favorite city either of us have visited! Some planning and a few activities were booked, but otherwise we explored where our AirBnB was and Googled local places to check out.
So if this is you, here’s everything we ate, saw and did while in Boston for the first time and would recommend you check it out too!
I’ll also share what we’d do differently or plan to try next time we visit.
This post is all about the top food and activities for your first trip to Boston.
Places- Beacon Hill Area
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.
Boston Common Park and Public Garden
This, like most things we did was a happy find! The weather was perfect and it was so cool to see so many people out and about in the park.
We got in around lunch time so a lot of people were in the park on lunch break. We’re not used to seeing a park actually being used!
We ended up stopping at one of the many stands throughout the park and got a lemonade. Perfect drink to have while walking through the park and checking things out.
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.
Florina Pizzeria
This happened to be just a couple blocks from where we were staying, and I so wish we went back! The pizza was huge and the perfect thin crust!
We ended up getting a whole pizza and took half of it home. They have a special and, at the time, it was $10 for 2 pizza slices and a canned coke of choice. The slices, easily a ¼ of a large pizza!
We could’ve easily chosen that but we got a spicy sausage and that ended up being 2 meals for us. They wrapped up the other half of the pizza so we could take it home.
Cheers
I LOVE the Cheers show. Super nostalgic for me and a comfort show I go back to when my other shows just aren’t cutting it for me.
Maybe it was because it was the end of a long day, our first travel day.
Maybe it was because I hadn’t seen the show in about a year.
But this was a bit of a let down.
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.
Mike’s Pastry
We picked these up while we were walking around before check in. We honestly passed it twice trying to find it because it was one of many places in a commons area.
We wanted to try a few different cannolis in the area, and Mike’s was one of the first to pop up. They had a lot of fun flavors along with other desserts, and we ended up getting 2 different kinds.
If you’re looking for a variety of cannolis I’d check them out. They were super good and extra filling after the pizza we had.
George Howell Coffee
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.
Bakey
Going around the corner for Bakey was well worth it! I can’t even tell you what kind of bakery it was, but the pasties were amazing!
We got 2 different breakfast pastries and a dessert one to split. I could’ve eaten a whole pan of them and been happy!
My only regret is that we didn’t go back another day, but I’d highly recommend stopping at least once. Staff was great and it was fun to see the bakers working in their open kitchen.
It’s also right across from the Boston Common Park so a great view and way to start the day.
Freedom Trail
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.
Tatte Bakery and Cafe
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.
Trillium
This was a find from my boyfriend and a bit of a walk from our location. But we took a break at our AirBnB beforehand so it was nice to go for a walk through another area of Boston.
We were there when at least 2 other parties or reservations were going on, so it was pretty full. But the beer on tap was so good! We got 2 rounds and were happy with all of our choices!
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!
Boston Sail Loft
This was dinner and, again, I could’ve gone back for more! We had a 40 minute wait once we got there, but put our name down and then just walked around to the docks.
This area was so pretty and it was nice to just have a chill time waiting.
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.
Beacon Hill Books and Cafe
I wish I got pictures of the book store but I was too focused on loving the moment! So breakfast pics will have to do.
Reservations area must of this place, but we somehow got lucky! We decided on just grabbing coffee, but once we got down there, they had 2 spots available so we grabbed them!
The food was amazing and the perfect size where we could still go exploring for the day without feeling super full and lethargic. Coffee was good too, we got a latte and just black coffee and it went perfectly with meal.
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!
Trinity Church
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!
Jonquils Cafe and Bakery
This was maybe a block from the church and online had the prettiest desserts! The kind you go just to take pictures of and post online.
They were pretty expensive, but had great flavor combos. Turned out to be a nice treat before heading back to hang out before the baseball game later.
Cash N’ Flagon
This was a bar and grill right next to Fenway Park, so it was a super easy stop before the game. It was pretty busy even 3 hours before the game started, but when you only have 2 people in your party, it makes seating a bit easier.
We ended up getting a couple drinks and the nachos as “dinner”. This was the biggest portion of food we had the whole trip and it was an appetizer.
Fenway Park
What is there to say about Fenway? This was the reason we went to Boston.
It was for my boyfriend’s birthday and seeing a game at Fenway Park was on his bucket list. So having the Minnesota Twins playing(we live in Minnesota) the week before made the perfect excuse!
Did we go to the ONE game they lost over their 3 game weekend? Yes.
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.
Paramount View Boston
This was a cool random thing to do! It’s a bit spendy, but it gives you a great view of Boston as a whole! And seeing it from the viewpoint when you’ve been walking around it for a few days made everything seem so small!
Like all the cool old homes and apartment buildings that were 3-5 stories high, seemed like such little toys from that height.
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.
Antonio’s Cuicina Italiano
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.
Recommendations for Next Time
Use the Public Transportation
I’ll be honest, we live in the midwest and drive everywhere or do a little bit of walking. I work odd hours and have places outside of the normal bus routes now and my boyfriend works from home. Needless to say there’s no public transportation in our daily lives and I’m an anxious person! We did use the Silverline from the airport to get closer to downtown which was great, highly recommend that! But when we got out to where the rest of public transport was it was super busy and we got too confused.
Then, when we walked back to take the Silverline again to get back to the airport, getting tickets was SO easy!
So if you’ve used public transport before this will be no big deal and you’ll be able to see a lot more without walking everywhere. But if you’re new to it and nervous, it’s really no big deal! Just give yourself time and it’ll make sense.
This may seem like a silly thing to say, but this can be a big adjustment if it’s not something you have available. So be brave and broaden your horizons!
It’s ok to Rest and Chill
This is more for my boyfriend who likes to do and see as much as possible, and being with someone like me who will take solo weekends to a cabin and just stay inside all weekend to recoup. This can be a huge balancing game!
But we did do well when we went to the baseball game. We went out and explored a few places, went back to the AirBnB for a couple hours to hang out then went back out to the game.
That was perfect!
Sometimes it’s nice to remember that vacations can be restful and doesn’t need to be go-go-go all the time to make the most of it. Finding that balance with 2 different types of vacationers is worth it and a little bit of give and take. But again, may be silly to say but it can make or break the vacation for either or both parties.
Enjoy!
Bring Water or Stop More Often
Water. Water. Water.
We somehow always forget about this especially with how much walking we do. And we tend to always be walking during vacations. So be sure to stop at convenience stores to grab a bottle of water or just remember to bring your water bottle with you. I know we would have enjoyed the days a bit more if we were hydrated rather than struggling through people to get back home.
If you need to, find a cute and fun little travel bag to hold your water and extra things. It’s worth investing in one and I wish we had that or just remembered to bring one of our backpacks with.
This post was all about the top food and activities for your first trip to Boston.
It honestly was such a great trip and one of our favorite cities for sure. We prefer small towns and countryside, so loving and navigating a city with little to no problem was a great change of pace!
Be sure to save this post to your board if you haven’t been to Boston yet and want to go, or be sure to explore the Beacon Hill Area on your next trip if you haven’t yet.
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