Boston, you’re the real deal

I’ve given it quite a bit of thought, and decided I don’t want to leave.

Don’t get me wrong, I am. (Mostly because the price difference to change my flight was astronomical.) But I want it on the record, right now, that I don’t want to go, and I’ll definitely be back.

Boston, you’ve held a bit of my heart since I was 14 years old. I came here to put you and my unparalleled ability to romanticize everything to the test, and you passed with flying colors.

So yes, Boston, I love you. And yes, Boston, someday I will call you home.

But until then, I’m heading back to my other heart and home, Chicago. And while I sit here at the airport terminal on this hazy but sunny Saturday morning, I figured I’d give whoever stumbles upon this a day-by-day account of the second half of my trip.

Let’s get started, shall we?


I slept in a bit in the morning, which to this morning bird, meant just after 8. I had breakfast at the AirBNB while reading my book, and the started out for my first adventure of the day: the JFK National Historical Site.

If you know me, you know how much I love, Love, LOVE JFK. And if you don’t know me, well, you do now.

So naturally, visiting his birthplace was high on my list of priorities for this trip – as was a visit to the JFK Presidential Library and Museum, but I’ll get to that later.

The JFK National Historical Site is in Brookline, Massachusetts – a somewhat lengthy, but definitely manageable, T ride away. I settled in on the green line with my book, and before I knew it – I was hopping off in the Boston suburb and ready for my first JFK excursion.

It was a snowy day in Massachusetts Wednesday – the meteorologists were suggesting anywhere between 3-8″, depending on who you asked and when. (I think it ended up being less than 3, but I digress.) The snow was fluffy and exceedingly picturesque, making all of the sweet houses in Brookline and the streets of Boston look even more magical.

So off the train and in the snow, I walked into the suburbs on the hunt for JFK’s birthplace, which I found…and then found out it was closed for the season. (Oops!) I had checked both my guidebook and Google before heading out, but at that point – I couldn’t get mad. In fact, I laughed. Something like this was bound to happen on my trip.

After a few pictures, and a great deal of standing in the snow, imagining what it was like when JFK was born and lived there, I noticed a light on the side of the house. Curious, and determined to double check, since I’d made it all that way – I went around back to the official entrance. Still closed, I determined, although I could book a tour. (Two weeks in advance.)

While processing this disappointment/wry humor, I noticed a sign posted for a self guided JFK walking tour, among other guided house tours. My interest was piqued: I was already all the way out here, and a walking tour seemed to be something I could do year round. I pulled up the site on my phone, and indeed – I could! So off I went, to get my JFK fix.

The walking tour was nine stops of significant places in JFK/the Kennedy family’s lives. Put together by the National Park Service, each stop was accompanied by a few paragraphs detailing the significance – and while some were more of a stretch than others, I loved seeing some formative places up close.

This spontaneous adventure, coming out of a disappointing closure, was honestly a highlight of my trip.

Along the way, my socks has become soaked from all the picturesque snow, so I stopped in a local bookstore to warm up. While my feet remained soggy (which a secondary stop at TJ Maxx for fresh socks fixed!), I did find a book of essays all about Boston – which I purchased to take a little piece of my new home back to the Windy City. I’m so excited to break it open next.

With dry feet and a JFK fix, I hopped back on the T and headed over to Cambridge. I walked through Harvard’s campus, which was even more beautiful in the snow, and then spent the afternoon at the Harvard Art Museum. I had the place nearly to myself, and was able to really pause and look at all of their incredible collections.

Spanning three floors, with research happening on the fourth and fifth, Harvard has (I suppose, unsurprisingly) amassed a wide-ranging and inspiring collection of art. From the modern (including, of course, my favorite – Jackson Pollock) to ancient works from Mesopotamia and Rome, I saw a bit of everything that afternoon. Standouts included some Renoir landscapes, my current obsession, as well as a curated dive into German art.

An afternoon well spent, in my opinion.

Stomach grumbling, I took the T into the city and stopped in the harbor at the Boston Sail Loft – a local joint with incredible clam chowder, which was literally served in a heaping coffee mug.

As I munched on this clam chowder, and later – a stellar bowl of lobster mac and cheese, which I’m still drooling over, I chatted with a guy sitting next to me. Turns out, he grew up and lives in Madison, and actually is considering an office in my hometown. What a weird, small world! These chance encounters have been my favorite part of traveling solo, and definitely part of the reason I’d do it again.

Stomach satisfied, and albeit, a bit exhausted, I wandered back into the snow, which had changed from delightfully fluffy to wet and windy and pelting my face. Hey, not everything can be perfect – right? I was tempted by the thought of my new favorite dessert, the cannoli, and decided what the heck, I’m on vacation. So over to the North End I went, gathering a cannoli for a sweet treat before bed.

A solid day.


Well rested from an early night, I got up bright and early to visit a local WW meeting before my day of touring. It’s a part of my week and so integral to my mental and physical health, so I try my best to fit it in even if I’m traveling. And I’m always so glad I did.

Refreshed, I hopped the T over to the JFK Presidential Library and Museum – where I spent literally the entire day. No, seriously. I arrived around 9:30 and left just before 5, and easily could’ve spent another hour or so there.

The museum was AMAZING.

I mean it, it was incredible. Both for a JFK devotee as I am, but also for an intense look at a fascinating period of US history. The museum is extraordinarily well curated, intensive but not overwhelming, and utilizes a phenomenal amount of video and audio footage to bring the history to life in an engaging, multimedia way.

Like I said, amazing. And I had the place (essentially) to myself.

No, seriously – a few school groups passed through, but rather quickly. Other than that, I saw no more than like 5 other people the entire visit. And while I got mistaken for a student/chaperone at least once, they left as fast as they came, and I was able to truly engage with the material with the attention and the time I wanted to devote to it.

And so I did. But perhaps my obsession with JFK, and my newfound little tidbits of knowledge, are best spent in another post.

The museum takes you chronologically through his life, starting with birth and his early years and then following though his time in the Navy, his senate run, his presidential campaign, and then his time in office. It dove into major challenges and successes in those three years, and then finished with his death and enduring legacy.

All in all, amazing. (Like I said, time for JFK in another post.)

After spending the whole day at the museum (even with rushing through the last exhibit! Information overload.), I grabbed something to eat quick in the museum cafe and hopped the T over to the Institute of Contemporary Art.

The ICA is a smaller museum, with a curated collection on only one floor. What it lacked in size, it made up for with breadth, including a video piece by Steve McQueen that’s still kicking around in my head.

The other highlight was a room devoted to an exhibit I had only previously read about in the New York Times, and it did not disappoint. Nicholas Nixon is a photographer who’s photographed his wife and her three sisters once a year for more than forty years – and every single one of those portraits was hung chronologically in this gallery.

Walking counter-clockwise around the room took you from his first portrait of the sisters back in 1975 all the way through his most recent portrait, taken in 2017. Watching the age progression and sisterly bond in a poignant manner was captivating, as you see the sisters age seemingly not at all, but then suddenly all at once. For me, it called into question my own perspectives on aging and family, and what it really means to see and be seen.

But despite this exhibit, which certainly was a highlight, I was not smitten with the ICA. While I usually am a contemporary art devotee, some pieces were still a bit avant garde for my taste – which leaves me to wonder if I would’ve benefited from some sort of guided tour. I made it through in barely two hours, and left with a sense of wanting, wanting more, wanting context, wanting something.

After my museum day, I stopped by a packed Irish dive in the financial district for a Guinness and then moved on to a second Irish dive that was slightly less packed, so I could have some dinner. Fish ‘n chips hit the spot as made friends with two different women that night, both with fascinating stories to share. Dive-y places are my favorite, especially when going somewhere solo. The relaxed atmosphere just welcomes conversation, as well as a far more reasonable tab.


My final day in Boston had arrived.

I had a slow start to the morning: breakfast at the AirBNB and packing the wide array of little things I’d managed to pick up throughout the week. (I flew in with a full suitcase and sorta had a feeling it was a mistake – a feeling definitely vindicated as I started to pack back up. Oops!)

Then, it was into the city for my least structured day of the trip; the only thing on the agenda was exploring. I had my sights set on a cool old bookstore I’d read about in Chinatown, a leisurely stroll through the North End, and a trip to Beacon Hill. Paired with a lot of great food and even more walking, it was a relaxed but ambitious day.

The old bookstore in question was Brattle Book Shop, an old used/rare books store in Chinatown that was one of the first hubs of literary history in the United States. And oh my, y’all, this place was INCREDIBLE. Multiple stories with shelves and shelves and shelves of every kind of book under the sun. Contemporary, vintage, rare – there was a little bit of everything.

Slightly overwhelmed, I wandered the aisles until I ended up in a tried-and-true section: historical/political non-fiction. It’s one of my favorite genres, and there were so many books I wanted to read. I’m pretty sure my TBR list grew a hundred fold in just a short visit. I limited myself to just one read, although I’m still adding others to my hold list at the library, and my suitcase was thankful. I’m not sure any more would’ve fit!

Elated, and with lungs filled with the fumes of old books (there even was an outdoor section in an alley, y’all!), I wandered over to the North End, stopping for a lobster roll for the start of my snacky lunch – which also included some local Sicilian food, a cannoli (of course!), homemade pretzel bites, and a scoop of ice cream, over the course of the afternoon. (Needless to say, there was no need for dinner… my personal food tour of Boston had me stuffed!)

While I munched my way through Boston, I explored the North End – so many cute shops! And bakeries! And corner family-ran places! – and then wandered over to Beacon Hill.

In Beacon Hill, I went to Charles Street for some boutique and antique shop exploring. I started on one side of the street, popping into all of the shops that caught my eye.

…which was, well, almost all of them. Seriously, it’s a wonder that my wallet escaped practically unscathed!

The antique shops have so many beautiful pieces, the boutiques are brimming with the preppy, classic clothes I adore, and then, of course, there are plenty of shops that are my weakness – stationary/gift boutiques filled with independent, artisan, and/or unique treasures. I could spend all day in shops like that! So many quirky little joys to admire.

I bought a local artist print of a Boston Street to take home and have framed, kind of a reminder of that “Boston feeling” I feel swelling in my heart whenever I think of the city… or heck, the entire time I was there! And smitten with my new treasure, I went back to the AirBNB for a much needed nap before determining my last-night-in-Boston plans.

My final night. I was so exhausted, but knew I couldn’t waste my last few hours in this city that I love. So after a nap, and a fresh coat of red lipstick, I rode the T into the city and stopped by two bars near the financial district.

In the second, I met up with two guys from Couchsurfing, a site that both fascinates and unnerves – and had an awesome time! They didn’t even know each other, but were so friendly and really showed me around their hometown on my final night. I’m so glad I took the leap: I made a new friend and had an amazing final meal (and a cannoli, duh. Plus this thing called a “peanut butter bomb” which was awe-worthy.) from a little Italian corner deli that couldn’t have been larger than my apartment living room. So tiny and cash only – my favorite.

Grinning ear to ear, I caught a ride back to my AirBNB for a few hours of sleep before heading to the airport.


Which leads us to today. I woke up early, packed the rest of my belongings, chatted with the German guy staying in another room of the AirBNB, and then headed over to the airport via the T.

Woah, was it a much different experience on the way out! I became so much more familiar and comfortable with the transit even over a few short days.

The airport is large, but TSA was a breeze, and before I knew it – I was here at the gate, waiting to board and writing to you. In a few hours I’ll be home, but as I mentioned in the up front: much of me really, really doesn’t want to go.


My trip was amazing, period. Traveling solo is the best!

I’ve been thinking and will be sharing some of the things I’ve learned about myself over the past seven days in another post. So stay tuned for that – and for now, well, grab a (another) cannoli. You earned it!