NYE in boston.
When Connor and I started planning our plans for his birthday (New Years Eve), we didn't anticipate winding up in Boston. Truthfully, we thought we wanted to go to New Orleans, but by the time we started planning, the plane tickets and accommodations were just too expensive for what we wanted to spend. So, I just started typing in cities until I found inexpensive tickets to Boston.
Having grown up not too far out of Boston, I was excited to show Connor around the city that I'd been so many times. We spent five days there and had a wonderful time.
We opted to stay in a little AirBNB in Back Bay which was in the perfect location. Despite it being nearly -10 every day we were there, we truly made the best of it. Boston is certainly a walkable city and we did our fair share of walking, but on colder days opted to use Lyft or the T.
We arrived early on Thursday and stopped in for crepes and nutella hot chocolates at the Paris Creperie in Brookline. The food was quite good, but the ambiance was lacking. I'd still recommend for a quick bite, though! We had time to kill before we could check into our AirBNB, so we pop into Olives and Grace and the Boston Library. My only regret is that we didn't end up making it back to the Boston Library on our trip.
After checking into our place, we headed to see the Mapparium. It was an inexpensive activity ($6 per person), and quite short, but a very fun experience. Technically, you're not allowed to take photos, but as can you can see, we didn't really listen. #SorryNotSorry
After an early morning flight and walking around the city, we opted for a long nap. The evening ended with a late dinner at Stephanie's on Newbury Street. We tried the mussels (loved 'em), salmon and the scallops. We were surprised by the portion sizes in Boston! While Chicago tends to be on the small-plate side, Boston portions are quite large.
We woke up early to travel to Jamaica Plain to tour the Sam Adam's Brewery. Our tour started promptly at 9:30am, and despite me not being a huge beer drinker, it was fun. We met a young couple there who we ended up traveling back downtown together and getting lunch.
After five or six glasses of beer before 10:30am, we desperately needed food. We headed back downtown and ate some delicious pizza at the Salty Pig.
After lunch, we bid our new friends farewell and headed to the Isabella Stewart Gardner Museum. With the bitter temps and kids out of school, it was pretty darn busy, but it was still very enjoyable. The museum itself is Isabella's own home which houses her love for art including some big names like Rembrandt. What I loved about the museum is that it's set up in little vignettes and also has the most beautiful gardens. The day we visited, there was a jazz trio playing which really added to the experience.
After the museum, we walked around a bit before ending with dinner at Union Oyster House. It was not for us and the only meal of the trip we didn't like. I will say that it could be because of what we ordered, but with better options out there, I'd skip it!
We knew Saturday would be the warmest day of the trip, so we planned on walking the Freedom Trail. We started the day at Tatte Bakery in Brookline. By then, we'd gotten the hang of taking the T, and was easy for us to go back and forth. It's a cute bakery with lots of options; there are a few throughout the city. We opted for avocado toast, greek style pancakes, and coffee.
After breakfast, we headed downtown to do some sightseeing. From walking through the cutest streets to walking most (not all) of the Freedom Trail, it was one of our favorite days. Connor and I opted to have a bit of fun with the walking and made this video.
Of course, we also need to walk to the North End to experience Mike's Pastry. I'm still in awe that Connor had never had a cannoli!
After so much walking, we opted for a late lunch / early dinner at The Green Dragon Tavern. It was serious bar food which was just what we needed, and we even got a seat next to the fireplace. Their fried pickles gave me life. We popped by Brattles Bookshop before heading back to our AirBNB to freshen up.
We contemplated staying in after a day of walking, but decided to rally. We headed to Wally's Jazz Club for music and a few drinks. We ended the night with two huge slices of pizza and laughing our faces off. It was one of my favorite nights of the trip.
Sunday was officially NYE and Connor's birthday! We ventured to the Punk & Poet for brunch which is located in South Boston. We didn't get to spend too much time exploring Southie, but brunch was great. We had the Buddha Bowl (me) and French Toast (him). After that, we headed to Beacon Hill for some antiquing. It's one of our favorite past times, and we found some really great items, including fleur de lis mini-ashtrays with matching matchbox containers. Knowing we were going to be out late, we came back & napped prior to dinner.
For dinner, we headed over to Cambridge to eat at Alden & Harlow. Of the places we ate in Boston, this restaurant felt the most like Chicago's small-plate scene. The menu changes quite frequently, but everything we had was delicious; I would highly recommend. The cocktails were wonderful, too.
After dinner, we headed to The Beehive where we had tickets for their NYE event with live jazz. We arrived promptly at 9pm, so we were able to easily find a seat at the bar...thankfully because the place was jam packed after that!
Monday was our last day, and we opted to be fairly lazy after quite a few very busy days. We had brunch, watched Netflix and ended our trip with lobster rolls and oysters at City Table. Connor had yet to have his lobster roll, and we couldn't leave without one!
It ended up being meant-to-be because our server was originally from Humboldt Park and grew up on our block!
Tuesday morning we headed home. Connor ultimately fell in love with Boston like I knew he would, and we already started planning our next visit!