Recently, I got a gift to do a walking food tour in the Mission of San Francisco. It was pretty cool, we got to try out some new places (one of which we loved), and check out some of the amazing art. We enjoyed it so much that I thought that it might be nice to do when we went to Boston, but looking into it, it focused primarily on the North End and Italian food, and honestly, I think there’s more interesting stuff than American Italian, as it’s incredibly easy to get in North Beach in San Francisco. That’s when the other half said, “Why don’t we just do our own?” It was a brilliant idea, because we get to share everything, try more stuff, and focus on more than just one area of town.
So, if you’d like to check out where we went and the route we took (and perhaps even do part of it yourself if you are visiting or live in the area), I’ve provided this great map and detailed route you could take to enjoy some or all of the things that we did while we were there! You don’t even have to do it all in one day (we didn’t), but the route I have created is definitely doable in a day, and while you might be full, you’ll be walking a lot to help out!
Start: Boston Cream Pie from Flour Bakery
Yeah I know, dessert first? Well that wasn’t my original plan, but by the time we got to one later in the day, the Boston Cream Pie was sold out. And rightly so, because it’s pretty much the best of the three pies I tried in Boston, and if you’re going to be there, you should definitely go for one of the better ones! The second time we tried, we got to Flour slightly after noon, and we got the last slice, so I highly recommend going early to get the multi-layered deliciousness from Joanne Chang, and I want the cookbook!
Stop 2: Regina Pizzeria
There are a lot of slice options in the North End, but Regina definitely was a great choice. You can order slices of cheese or pepperoni to go (unless you’re really hungry, and you can have a whole pizza there, as there were some amazing looking choices). We opted for the pepperoni and scarfed it down outside the restaurant. It was a great crust, and a very traditional American style slice! (But I’m sure there are others nearby you could also go to, depending on the slices you are looking for!)
Stop 3: Galleria Umberto
This place does basically two things: Sicilian slices and arancini, and if you don’t get there early enough, they could be out, so we made sure this was early on our agenda for trying out. We went with an arancini, and we were not disappointed. It had a very crunchy exterior with a really delicious meaty filling. They are cash only though, so make sure to grab a bit of money before you leave!
Stop 4: Modern Pastry (or Mike’s… or both!)
There are two top cannoli contenders in Boston, and they are right down the street from each other, so stop into one and get a pastry to try. There are long lines at both, so be prepared. We opted for Modern Pastry because they fill their cannoli to order (we weren’t sure about Mike’s), but Mike’s offers a lot more flavors, so really, it just depends on what you prefer. We went for a classic ricotta filling with pistachios, and we were not disappointed as the shell was super crispy and the filling was incredibly smooth and tasty! If you’re lucky you can grab a table to quickly eat it, but you may have to take it with you! Another cash only venue so at least the money you took out of the ATM will still be useful!
Stop 5: Faneuil Food Hall
We had actually come here the day before, but it’s so close you can definitely just swing by after you are finished in the North End to try some other Boston eats. There are plenty of options here, but we went for a hot buttered Lobster roll, and it was definitely the best of the trip! The lobster was perfect, and the butter was delicious. Sadly, I can’t remember which one of the several places to get them we stopped at, but I think it was the most expensive one, because it must be best, right? Or you could just try them all and decide which one is best for you. Depending on when you start, there is also a great Escape Room nearby called Boxaroo, which was the best one we’ve ever done, so you could always take a break and solve some puzzles before continuing your walk through Boston!
Stop 6: James Hook & Co
More Lobster? Don’t mind if I do! After a nice walk along the waterfront, you can grab the other kind of Lobster Roll: The cold one that is mixed with mayo! They offer two sizes, and since we had more stops planned, we went for the regular sized one, but if you’re feeling like a splurge, you can always go large! And while it’s not quite as good as warm butter, you do get to sit outdoors near the water, which is always a plus. They offer beer as well, if you’re feeling ready to start day drinking!
Stop 7: The Barking Crab
Just across the bridge to the Waterfront there is a great venue called The Barking Crab. People love it so much they have some not-so-pleasant signs reminding you that you can’t just sit there and drink, you must order food. But that was okay with us, because we were hear to get some New England Clam Chowder! And it was definitely a great version of it with soft clams, creamy soup and bacon! Again, if you’re ready for drinks, have a beer and chill, but we were planning on beer and the next location, so we just had our soup and got going.
Stop 8: Trillium Brewing
Just down the street from The Barking Crab is local brewery: Trillium Brewing. They have a large selection of beers, from IPA to sours to stouts. They offer beer by full glasses or smaller pours if you want to try more, and there’s even food on the menu, but we decided just to have some drinks! Stouts all around!
Stop 9: High Street Place
As the day has gone by and a lot of walking has been done, you may be ready to just go somewhere and chill, and High Street Place is a great place for it. It’s a great indoor food hall with a lot of different places to try out, and a fantastic wine bar to hang out at and have some wine! If wine isn’t your thing, there is also cocktails and beer, allowing for plenty of options for whoever you are with! We tried a burger (that was fantastic), some happy hour oysters ($2 each!), a mixed container of fries and rings, and a chicken burger. And there were plenty more food vendors available too!
Final Stop: Yvonne’s
Our last stop was at Yvonne’s, which we had heard about from the bartender at the wine bar. She recommended it because it’s pretty old school and deluxe looking with two bars inside to sit at. It was a great way to end the night as they have a fantastic spirits list, and we managed to have a few different spirits and some dessert to boot! The service was great, and they do have some interesting cocktails available to try as well.
While I highly recommend any walking food tour that you may opt to pay for an be lead on, there was something awesome about planning one myself and trying some places. If you like to do things at your own pace, and you like to have options of things to try, I highly recommend following some or all of my route and seeing what Boston has to offer!
