Some people form habits with restaurants, repeating them again and again, even after they’ve just been there. It’s like being in a rut but in the good way. Well I form habits with cities, returning again and again, like an addiction I can’t shake.

My current addiction is Boston, where I found myself last month even though I was there last year, the year before and a few years before that. I just can’t seem to get enough of it. And I’m perfectly fine with that.

A Week of Food, Family & Friends in Boston

Boston is an enchanting place, luring tourists to its charm, history and distinctly New England accent. For me, the allure is all that and more: It’s one of the best food cities in the country. Its baseball stadium is practically a magical holy place. And it has a vibrant energy and pride that’s distinctly, uniquely, Boston.

The trip was inspired by two equally awesome factors: my parents were going to Boston for their first time and my friends recently moved there. With the city just a two-hour flight from Chicago, I had to go.

Boston Must-Dos

Luckily my parents are as obsessed with food as I am and were more than happy to half-ass The Freedom Trail, which is a Boston must do, in exchange for wandering through the city in search of food.

Neptune Oyster is as much of a Boston requirement as The Freedom Trail, so we put our name on the notoriously long wait list (3 hours that day) and leisurely followed the Freedom Trail until we found a pizza place. Yeah, we ate while waiting to eat. The lobster rolls at Neptune Oyster put the tiny oyster bar on the national radar. They are routinely named the Best Lobster Rolls in Boston/New England/the United States, even though the executive chef has never actually eaten one. Paired with a glass of crisp Albariño, the buttery chunks of lobster instantly signaled that I was, indeed, in Boston.

We walked off our lunch through the winding streets of The North End, marveling at how old the buildings and bars were. We stopped in historical cemeteries (my favorite) and churches, like The Old North Church (made famous by Paul Revere’s “one if by land, and two if by sea” lanterns).

Exploring Boston’s Back Bay Neighborhood

The next day we started with brunch on Newbury Street, then wandered through The Boston Public Library, one of the most striking libraries — if not buildings — in the United States. The “Palace for the People” was built in 1895 with elaborate detail, stunning reading rooms and a courtyard that instantly transported me to Spain.

Across the street, the Trinity Church is also a must see. The historical building is practically an art museum, with stained glass windows and over 21,000 square feet of murals. The American Institute of Architects named it one of the Ten Most Significant Buildings in the United States and it remains the only building on the top ten since 1885.

Steps away is a restaurant disguised among brownstones called Saltie Girl, where my friend and I shared a lobster bacon cheeseburger and fried caviar gnocchi that tasted awfully life-changing. They catapulted Saltie Girl to a can’t miss restaurant in Boston.

A Day Trip to the Cape

Spending a week in Cape Cod has become a summer tradition since I moved to Chicago and I wasn’t about to break the habit this year. Plus I wanted to show my parents Provincetown, but we only had a day to spare and I wasn’t sure a day trip to the Cape was possible.

Turns out, it’s completely possible to do a day trip in Cape Cod from Boston, thanks to several ferries that leave the city every morning and return every night. Stay tuned for all the details on how to get to Cape Cod for the day and what to do once you’re there.

Our day in the Cape morphed into an impromptu bar crawl because it was so much fun stopping in all the little restaurants while exploring the historical town. We made sure to have legendary clam chowder at The Lobster Pot and dinner at the epic Red Inn before ferrying back to Boston.

The Boston Bucketlist: Fenway

Like the rest of my trips to Boston, the highlight was cheering on the Red Sox at the iconic Fenway stadium, the oldest baseball stadium in the country. (The “oldest blank in the country” is beginning to sound like a broken record at this point, isn’t it?) No matter how many times I visit Fenway or where in the stadium I sit, the energy is always incredible. From standing on the Green Monster to box seats and everything in between, there is a powerful pride that Boston fans have that permeates the stadium like none other I’ve ever been to.

Every strike thrown, every run scored feels like the winning play of a tie-breaking game at Fenway. Fans erupt in cheers on good plays and rowdy boos on bad calls. Maybe that’s because it barely holds 37,000 people. Maybe it’s because Bostonians are obsessed with sports. Whatever it is, it’s uniquely Boston and it makes going to Fenway an absolute must in the city.

Iconic Food

On our last day, we had one simple agenda item. We’d eaten all of Boston’s iconic foods — lobster rolls, clam chowder, oysters and Italian food — except one: Boston Cream Pie. Somehow I’d managed to miss it every time I’d been to the city.

So we went for the original. Boston Cream Pie was supposedly invented at the Parker House Hotel in 1856. Like many places in Boston, the Parker House has a string of historical accomplishments. It’s the oldest continuously run hotel in the country. It’s where Charles Dickens lived and first performed A Christmas Carol. Where Jacques Offenbach found inspiration for his opera Tales of Hoffman. And where John F. Kennedy proposed to Jackie. Oh, and Malcolm X, Ho Chi Minh and Emeril Lagasse all worked there — before they were famous, of course.

The Boston Cream Pie is served in individual mini cakes, made with the original recipe (that’s available online), with its sides coated with tiny toasted almonds. It was a perfectly sweet and historical end to our week in Boston.

Boston is a Time Capsule

On our first day, we covered almost the entire city on foot. Just by traversing Boston we crossed through centuries of time. We started at Boston Common (the oldest city park in the country dating to 1634), weaved through the Back Bay’s iconic brownstones from the 19th Century, passed Fenway (the nation’s oldest ballpark built in 1912) and finished at my friend’s apartment, a high rise just a few years old.

For me, part of Boston’s magic lies in that simple story: the way the city itself is a time capsule and how walking through it feels like a time lapse of American history. So much of what we hold sacred to us as Americans is contained within Boston’s streets, even down to the baseball stadium.

As you can tell, my infatuation with Beantown isn’t ending anytime soon. Old habits die hard, and Boston isn’t one I want to quit.

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Thank you James and Emily for hosting me in Boston! Can’t wait to return the favor when you come to Chicago. :)

Related :: Why Neptune Oyster is a Must Visit in Boston, Where to Eat in Cape Cod, and Where to eat in Boston