Bar Crawling and Italian Food in Boston’s North End

Any chance that I had to get a head start on bathing suit season was quickly put to rest once I was set loose in Boston. I planned my stay in the big city around the 2015 Women in Travel Summit (which was really excellent, in case you were wondering), so for possibly the first time in my life, food took a back seat to other travel activities. Somehow though, following suggestions via word of mouth rather than the usual scrounging up of every Internet detail and Yelp review turned out wonderfully. I didn’t have a bad meal while we were in the city.

On the contrary, everything I had was pretty damn excellent. Without trying, no less! Don’t worry, this isn’t a lesson I’m going to learn from or anything. I’m certain that I’m doomed to continue my neurotic restaurant research.

Not that I should’ve been surprised (“Hey, you know we broke the record for snow this year, right?” was a common refrain), but it snowed nearly the whole Saturday we were in Boston. Luckily I was occupied with WITS stuff, so it wasn’t a letdown. We were also staying through Monday so we had some free time to explore.

The Seaport District

On Sunday, when the sun finally came out and the temperatures went up a bit, the city was alive with tourists and a shitload of pedestrians. My law school friend Anderson lives in Boston, and he ended up driving around with the windows down, blasting Eric Church, you know, because the weather was just so great. (Leaving North Carolina and the South since graduation has caused him some severe withdrawals.) Keep in mind, it was still only about 45 degrees out.

During our tipsy Saturday night meet-up, Charlie, Anderson, and I decided that the following evening, we would come to his ‘hood, the North End, and have a delicious Italian dinner (preceded by several drinks, of course), check out his pad, and taste test Boston’s most famous cannolis.*

And for once, drunken plans panned out. After an already delicious day, Anderson graciously came and picked us up at our temporary abode in Back Bay and drove us to our first destination: Legal Harborside, a rooftop, waterfront bar in the Seaport area of Boston (which I’m sure gets super hoppin’ when it’s really hot outside). We each had a beer and checked out the beauty that is a big city located right on the water. Seriously, if we wouldn’t have gone there, or flown in over the water, I might have forgotten that Boston was even on the coast. (Aside from all the advertisements for oysters and lobster, of course.)

I quickly lost all shame and wore my camera around my neck, taking photos of unassuming folks on the boardwalk, all the boats and the seagulls next to the bar, and the skyline across the water next to Logan International. Then I made Asian tourist jokes about how it would look more natural if Anderson wore my camera around his neck. Oh yeah, Anderson is Asian. Don’t worry, he can take it.

A Faneuil Hall/Quincy Market Stroll & The Salty Dog

Next we headed to the North End to begin our cultural exploration of the city (kind of…). We strolled through the Faneuil Hall and Quincy Market area which I’d meant to hit up for its variety of food choices but never did, so this was perfect. There was still snow on the ground, tons of people out and about, and we continued to have some great views of the Boston skyline. We even joked about heading into the giant Abercrombie store they have here, and how Charlie’s sixth grade self would have been overjoyed about this. Okay, let’s be honest, we all would’ve begged our moms to let us go in.

From there, we made the game time decision headed into an underground bar at the Salty Dog. (No relation to the Hilton Head place where everybody buys T-Shirts, our bartender informed us).

It was tight quarters, a little kitsch, full of neon, and they let us put the Duke game on, so I was happy. I took lots of pictures, totally creeping out the bartender as he shucked oysters. Ah well, I was a tourist in Boston, a first timer, in fact, so that’s allowed right? I fought the urge to order clam chowder as a snack to go with my beer (because, you know, when in Boston) as I knew we had an Italian feast ahead of us.

The North End & The Green Dragon Tavern

From there we headed to the narrow, brick and cobblestone streets of the North End to The Green Dragon Tavern, the bar where it’s rumored the American Revolution was planned. Paul Revere and John Hancock hung out here, you guys! I’m a sucker for really American and patriotic things (I’ve cried during the National Anthem before, but give me a break, it was a college football game, post-tailgate festivities, and a lovely Carolina blue sky was in effect), so I got really pumped about this. I can’t say that there was much to the decor to reflect the history, but I was just happy to be there, drinking in a bar that was established in 1654. George Washington would have been proud.

We then strolled around the North End as we neared our reservation time. The great tour guide that he is, Anderson led us to the North Church where ol’ Paul hung up his lanterns using that “one if by land, two if by sea” code. Man, the history around here is really unbelievable.

An Italian Feast at Carmelina’s

Finally (finally!) we made it to our Ultimate Italian Dinner destination, Carmelina’s. Anderson has been slowly checking off all of the high-ranking Italian eateries around his place, so we were happy to join him in his research. A tiny, old, super Italian man greeted us at the door and took us to our table by the kitchen. We ordered bottles of red wine and, of course, we were served fresh bread because that is a legal requirement at all serious Italian restaurants.

We chose the mussels in white wine and garlic sauce to start and our server generously offered us MORE bread to sop up all the juice… well the juice that was left after I started ingeniously began scooping it directly into my mouth with makeshift spoon-mussel shells.  By this time I was bold (tipsy) enough to break out the camera and take food photos even in the low lighting of this classy, authentic establishment. Sorry I’m not sorry. Anderson even joined in on the fun.

For our main courses, we all had homemade pasta. Charles went with the classic savory carbonara, I had a great fettuccine with tomato cream sauce, shrimp, chicken, and sausage, and Anderson had the frutti de mare which contained every type of seafood ever, including more mussels. (PS – It’s taking all I have not to type “muscles,” every single time.)

The Cannoli Challenge!

We polished off nearly all of our food and (obviously) all of the wine, and purposefully skipped dessert so that we could end our night with THE Cannoli Taste Test: Mike’s vs. Modern.

Mike’s Pastry is pretty much a Boston legend. It was packed with people inside and out as we passed by before having dinner. Folks were lining up down the street. After dinner (this is like 10 PM), the crowd had gotten a little better, though the line was still to the door. They only take cash, and they have a wide assortment of desserts. Hell, they have a wide assortment of cannolis.

Modern Pastry Shop is located on the same street just a few steps away. Direct competition. It’s over 70 years old, also only takes cash, and has pretty much the same feel as Mike’s with all its desserts. However, it did have a noticeably smaller crowd. Anderson told us ahead of time that Modern was his favorite. We grabbed a cannoli (with the ends dipped in mini chocolate chips!) and a tiramisu from each place… for science.

With our laughably similar string-tied boxes from each pastry shop we popped up to Anderson’s place (which is ridiculously full of North Carolina paraphernalia, of course). And there, over an after-dinner bourbon, we carefully cut each cannoli and tiramisu in half to taste test and pick the winners – I was too distracted/talking too much to get a comparison shot of the cannolis before they were cut into pieces. Living here, Anderson has obviously already done this challenge, so he left this one to us. Charlie crammed both of his down this throat before I even had a chance to inspect the situation, loudly proclaiming Modern the champion.

Personally, I would have preferred to perform this experiment without so many outside influencers and opinions, and maybe a palate that wasn’t numbed with so many drinks and plates of food, but I gave it my best shot. Taking a bite of Mike’s first, I exclaimed that I didn’t see how any cannoli could possibly be better than this one, ever, like ever ever.

But honestly, to me, Modern’s tasted almost identical. I tried my hardest to discern the subtle differences, but with no real support or distinction to report, I say that Mike’s is the winner. There was just something about that first bite [there’s gotta be a joke to be made here using The First Cut is the Deepest as the punchline, but I won’t subject you to that]. To further verify these taste results, I would need approximately three more unshared cannolis from each place.

I was so impressed with our glutinous romp around the North End that I feel like I must return to Boston to eat all the things (there’s still fresh seafood to be had!). Everything we ate bordered on phenomenal. A big thanks to Anderson for leading us on this impromptu food and drink tour. He’s still a lawyer, but I’ll be sure to report if he decides to take his talents to the food tour circuit. Hanging out with a local definitely made this experience more fun, and the food and camaraderie couldn’t have been better.

And this wasn’t the only serious eating we did in Boston. I also developed a strong love for Chinatown…

*I have since learned that the plural of cannoli is just cannoli. The singular is cannolo. However, I will use “cannolis” incorrectly throughout this post.

So have you guys ever been to Boston? The North End? Have a favorite Italian spot? A favorite cannoli?