Planning where to eat during our four-day trip to Boston was more challenging than I imagined because there was just no way to hit all of the amazing restaurants and eateries. Not to mention, we consumed three meals at Fenway – which we have no regrets about. After reading millions of restaurant reviews, we narrowed our options down to what we thought were the best of the best. Most of the places we ate and drank far exceeded our expectations, but there were a couple of “must eat” spots that still have us scratching our heads.
TATTE BAKERY & CAFÉ
Tatte Bakery & Café was our very first stop in Boston. By the time we arrived it was 10 am and Jordan had been awake since 1 that morning – we were in dire need of coffee. I found Tatté on Instagram, which is not surprising because every location is very “gram worthy”. We went to the Beacon Hill location, but they also have spots in Back Bay and Fenway (coming soon), as well as several locations in Cambridge and Brookline.
The Beacon Hill location is located on a corner of Charles Street – the main strip in Beacon Hill. The café was practically bursting with people so I had a hard time getting any good images, which is too bad because the whole space was beyond amazing. They have pastries galore, an expansive brunch menu and all of your coffee needs. I ordered a vanilla latte and a slice of galette that was calling out to me from inside the glass case. I swear it. Jordan ordered an iced latte (wise choice) and the breakfast sandwich. Everything was delicious and provided the perfect amount of fuel for the rest of our morning.
The Paramount is the most recommended restaurant in Beacon Hill. Everywhere I looked told me that this was the spot to go. It’s a long and very narrow restaurant with minimal seating, but they somehow manage to have a seat for everyone once your order is ready. You order at the counter and watch them prepare your food – kinda like Chipotle? You pay right at the counter and someone carries your food to an open table.
Let me cut to the chase here – no. We didn’t like The Paramount even a little bit.
Boston is just covered in Thinking Cup locations, and we didn’t hate it! Thinking Cup is an awesome café that’s perfect for breakfast or an afternoon pick-me-up. We went to the North End location once, but we visited the Back Bay location at least three times because it wasn’t too far from our hotel. Everyone should definitely visit Tatte, but Thinking Cup is the spot you’ll keep going to.
LA FAMIGLIA GIORGIO
Boston’s North End has more tiny, authentic Italian restaurants than you can imagine. We’ve never been to Italy, but the North End is exactly what I imagine an Italian village would feel like. La Famiglia Giorgio was the place that every website and review told us to go, so we did. It felt like a risk after our experience at The Paramount, but we went with it. This time, the internet did not lie – SO YUM.
We ordered homemade pasta with marinara and the stuffed mushrooms. Everything is served family style, so don’t be like one of the couples near us and order two dishes… The marinara was great, but I would recommend ordering something a little meatier. When we go back we plan to try some of the other restaurants, but La Famiglia Giorgio would always be a great choice.
Mike’s Pastry was probably the most recommended thing to do/eat/see in Boston, so we made sure to go! Mike’s is in the North End, always full of people and cash only. Neither Jordan or myself had ever had a cannoli, so we each ordered one and took them back to our hotel room because we were still full from our Italian lunch.
I’m afraid to admit it, but we didn’t like them. I’m so sorry, Boston! That being said I still recommend going to Mike’s Pastry because it’s a Boston institution and you probably will like cannolies!
UNION OYSTER HOUSE
We knew that there was only one night we would be eating in Boston, not at Fenway. You better believe we did a lot of research to determine our one and only dinner out. Union Oyster House came out on top, mostly for its history. Union Oyster House is the oldest restaurant in America that is still operating, and also – seafood. The restaurant sits on a block that has maintained its 1800’s character phenomenally well. It feels very colonial, but also very Diagon Alley.
The interior of the restaurant, while it has obviously been updated, has a very ancient feeling to it as well. The ceilings are low, the floors are creaky and uneven and it’s kind of dark – we loved it! We had a reservation and we were sat almost immediately after our arrival. Everything was more casual than I imagined, especially our server, but I was grateful for her humorous spirit! Jordan and I were going to order an appetizer, chowder (duh) and an entrée. Our server immediately told us that we would be incapable of consuming all of that – ha! We explained that the chowder was non-negotiable, so we skipped the app. Jordan ordered the Ye Olde Seafood Platter, which is an array of fried seafood goodness. I’m actually salivating just thinking about it. TMI? I ordered the Lobster Scampi, which was also very delicious! Next time we go to UOH, we’ll probably each order a bowl of the chowder and the Ye Olde Seafood Platter to share. Or maybe, maybe we’ll just order double the chowder.
Unless you have a shellfish allergy, go to Union Oyster House! It’s just a fun experience.
We stumbled upon Upper Crust while touring Beacon Hill for a second time. I actually turned it down, but when we couldn’t agree on any other place I decided to give it a try. Good thing, because it turned out to be one of my favorite little spots! They appeared to do a lot of deliveries, but inside their little store you can order pizza by the slice. It was the perfect lunch and we loved the pizza!
Don’t you want to visit Boston now? I’m so glad we tried all of these places on our trip, good or bad. Next time we visit Boston we’ll be sure to try new places, but you’ll definitely find us at Thinking Cup and Upper Crust again. If you’re a Boston expert and know of any places we must try next time, send me an email or share in the comments!