Hey guys! So last weekend Stephen and I took a quick trip to Boston to visit my sister! Most of the tourist activities we did included eating and drinking (per usual lol), but thought I’d round up where we stayed, and all the places we went to. These were all places that either my sister or our other friends that live up there recommended – so all of these spots were their “local” picks (versus us randomly googling what to do haha).
Where We Stayed
We stayed in this Airbnb in South End and the location was perfect! It was in walking distance to a ton of restaurants, a park, and the street/surrounding streets were lined with the cutest brownstones. Also, it was less than 10 minutes from the airport and if we went anywhere outside of South End, it was a pretty short Uber/Lyft even with traffic. Aside from the location, the apartment itself was perfect for 2 people. Cute, clean, full kitchen, AC, etc.
What We Did / Where We Ate
Carmelinas – Really good Italian spot in the North End. They have a cute outdoor/street set up so we ate here and then walked to the comedy show at Improv Asylum right after. There were 7 of us at dinner and everyone said their entrees were delicious, and the apps we got were really good as well!
Comedy Show at Improv Asylum – Walked here right after dinner at Carmelinas (so also in the North End). I will say that Stephen and I were both very skeptical about an improv show because usually people aren’t that funny BUT we were both pleasantly surprised. The show was really entertaining and funny. Stephen was next to me and was like cackling the whole time – and he is a tough critic! Haha. My sister and our other friends have been to shows several other times here and they said they have always been good. They have a bar at the venue as well if you want to order drinks during the show.
Monument Restaurant and Tavern – This is a restaurant in Charlestown that we went to for brunch – so good!! Everything on the menu looked amazing and it was so hard to decide; there is a lot of variety and something for everyone. We ordered their doughnut holes for the table as an app and you can also order a champagne bucket for the table if you’re in the mood for mimosas. Some people in our group got bloody Marys which looked amazing as well.
ReelHouse – After brunch at Monument, we walked down to the waterfront and took a boat from Pier 6 over to ReelHouse. As a side note, from what I understand Pier 6 is a pretty popular spot but we didn’t eat/drink there. But by the Pier 6 dock, there is a boat (like a speed boat of sorts lol) that goes back and forth from there over to ReelHouse which is the restaurant on the other side of the waterfront. The boat is free, but you can tip the driver with cash or through Venmo. Anyway! We had the boat take us over to ReelHouse and we had drinks outside on their patio while we waited for Tallship to open.
Tallship – Tallship is, well, a tall ship lol, that is docked at the the Boston Harbor with a full bar on board, plus a turf area right next to it with picnic tables, food trucks, cornhole, etc. So you can either hangout on the actual boat or in the other area. Hopefully my photos below give you a better idea of the set up! It opened at 2pm (we were here on a Saturday) and so we got there at 1:45pm and the line was already fairly long. Once they opened and started checking ID’s though, we got in pretty quickly. If you do plan to go here, I would do like we did and get there before they open. It’s my understanding if you get there later, they will probably be at capacity and you will either have to wait in line for a long time or just won’t get in!
Picco – This was a spot that was close to our Airbnb that we grabbed pizza from one afternoon! Really good pizza (and they have ice cream too) if you’re in the area and want to grab it to-go or have a casual meal on their outdoor patio.
Lolita – This is a Mexican restaurant in Back Bay which is definitely a vibe! A good amount of y’all messaged me saying it was a spot you loved to go to for special occasions, if you wanted to splurge, etc. It’s not crazy expensive, but definitely a more upscale Mexican restaurant. I got the Diablo to drink (serrano infused tequila, lime, blood orange, strawberry) and really liked it if you like a little spice. When you first sit down they also serve you this tequila and dry ice concoction which you drink with little spoons haha, it’s hard to explain so I put a video below. And at the end of the meal they also serve the table cotton candy as well! The only thing I’d say is that it’s really dark and pretty loud in here, so definitely not a spot I’d bring my parents too haha.
South End Buttery – This was a little breakfast spot that Stephen and I walked to from our Airbnb Sunday morning and if you’re in the area, definitely recommend if you want to get pastries/baked goods to-go or if you want a more casual breakfast. They have their to-go cafe menu, outdoor seating, and then indoor seating as well (they have a downstairs area which is where we sat) that has a full breakfast menu. I got their brioche breakfast sandwich with potatoes and I will say, they nailed it on the crispy hashbrowns!
Newbury Street – Y’all have probably heard of this street before but it’s where there is a ton of shopping (designer shops too) and restaurants. I had to make a stop at Zara when I was here and otherwise we just walked around and window shopped/browsed. It’s a cool area/street that is probably worth a stop even if you aren’t shopping per se!
Harpoon Brewery -This is where we headed after Newbury St on Sunday and it was the perfect way to end the afternoon. We ordered some beer flights (I loved their UFO one), baked pretzels, and checked out their merch (where I ended up getting a cute baseball cap). It’s also right by the Seaport which is (from what I could gather lol), an area with restaurants, hotels, shopping, etc. So if you go to the brewery, you can walk through this area before or after and grab a bite, and also check out the waterfront!
If any of y’all are from Boston or have visited and have any other recs, please share below!