Greetings from Boston

I’m here, I made it, and I’m in the midst of my fourth full day here in Boston.

When I made the decision to add solo travel to my 25×25, I was terrified – what if I hated spending that much time alone?! – as well as excited – imagine how much fun it could be to do only what I wanted to do.

And now, four days in – I gotta say – it’s exactly as fun as I thought it would be!

I’m not sure why I’m surprised, but in a way – I am. I’ve always considered myself independent, but this trip has been way outside my comfort zone. Heck, eating alone at a restaurant or ordering a drink at a bar by myself is way outside my comfort zone! But now I’ve had dinner solo 4 times, and I can say that it’s honestly not as bad as I thought it would be.

It’s honestly kind of nice.

And while there have been moments where I wished I was sharing an experience with another person – for instance, some of the art I found at the MFA yesterday! – for the most part, I’ve been totally content being solo. It’s been the perfect trip for me, myself, and I.

So a quick recap of what I’ve done so far, and I’ll share more throughout the week. I’ve been doing my best to go dark on social media so to fully immerse myself in this city and everything it has to offer. And to my surprise, I haven’t really found that all too challenging.

But alas, for my memories, and your (hypothetical) curiosity:


I was off to the airport mid-morning for my flight to Boston. Navigating the L with baggage is always a pain, but luckily on a weekend, the trains are less full.

The same cannot be said for the TSA. I made it to the airport and stood in a long, slow line for security – reminding me why I always fly late in the evening or early in the morning. Another side observation: it seemed most people were heading on ski vacations, and I was strangely jealous. I wrote off skiing in high school, but am considering trying to learn again.

I got distracted at work the day before, so I ended up in the C group. It’s a perk and a downfall of Southwest, not having assigned seats, so I ended up in the middle seat between two women who slept the whole way. We took off, I started my current read (which I am OBSESSED with!) and before I knew it, we’d landed in Boston.

It was off the plane, onto baggage claim (there’s an argument that I simply have far too many toiletries), and then I figured out the shuttle and T, rather than paying $20 for a Lyft. I’m so glad I did, because the first time was the hardest, and every time after has been a breeze! And my 7-day pass for twenty-ish bucks has paid for itself like ten times over by now.

After the struggle of figuring out how to exit the T station and make it to my AirBNB, I finally made it, I got in and got settled. The neighborhood has a bit to be desired, but it’s literally a three minute walk to the T, so honestly – good enough for me.

I dressed for dinner and then ventured out for my first solo meal, nervous but also excited to explore the city some more. I ended up at B&G Oysters in the Back Bay, where I had oysters (shocking!) and this Atlantic cod fish which was killer…and had Brussel sprouts that were to die for. Seriously, still thinking about them.

Dining alone was probably my largest anxiety with this trip, and I’m happy to report that it’s not nearly as bad or as awkward as I imagined it would be. I’m able to slow down, enjoy the food, enjoy the atmosphere, and truly get lost in my own thoughts. There’s a lot to be said about mindfulness, and setting your fork down after every stinking bite.

Plus, at B&G Oyster, the bar overlooked an open kitchen – so I always had something to watch. (Or someone – I can’t lie, the kitchen staff was cute!)

After dinner, where I got bit in the booty by a $12 seltzer charge (oops!), I caught a Lyft deeper into the Back Bay to this divey bar I’d hear about called Bukowski Tavern. My #1 goal when I travel is to avoid tourist-y spots and to not be a shitty tourist, so I’m always on the hunt for where the locals actually eat and actually drink.

(This being said, I’m not above a few touristy stops – after all, they’re touristy for a reason!)

But alas, I ended up at Bukowski Tavern, which did not disappoint. Dark, dingy, and cash only – it was my absolute favorite kind of bar. They only had beer and wine, so a local beer it was, and I ended up chatting with this guy from South End about his life, my trip, and just about everything under the sun. I called it a night just before midnight, and truth be told – it was a pretty stellar first day.


I didn’t set an alarm on Sunday morning, but I still was up just before 8 – pretty standard for this morning person, especially when taking into account the time change. I had a quiet start to the morning, got ready for the day, and walked over to Trader Joe’s for some breakfast and snack provisions for the week – partially to save money, but also because I crave healthy food and breakfast is the most important meal of the day.

After breakfast, I took the T over to the Isabella Stewart Gardner Museum, where I spent my late morning/afternoon. It was INCREDIBLE. Isabella Stewart Gardner amassed this astounding collection of art and then opened a museum to share it with the public. I spent most of the day there, and even got in for $5, thanks to my student ID!

I started in the new wing, which housed a Henry James exhibit, and explored her relationship with this famous author. It was fascinating to see the overlap of the art and literary world, and it was the part of the museum which felt the most like an actual museum – the rest felt like wandering an old mansion, packed with art.

I even discovered a new-to-me, might-become-a-favorite artist: John Singer Sargent. His work was awe-inspiring and frankly, moved me. I’m struggling to really find the words.

Also, I need to learn more about his peer James McNeil Whistler – his work was beautiful, but also he seems so petty and hilarious. He wrote quite a few pieces defending his work and calling out critics, I simply had to chuckle to myself.

After the exhibit, I made my way over to the original part of the museum, where I gave myself permission to just enjoy the art, to be present and see it, and not feel pressured to read everything. I know it seems simple, but this was truly life changing for me. It’s completely altered how I viewed the museum, and I had an amazing time. (Double emphasis necessary.)

I’m usually a read every plaque, page, wall kind of person, so this was outside my comfort zone – and entirely freeing. I think I’m onto something.

After a few hours of exploring, I was experiencing a bit of art overload – so I took off and decided to make a few stops along the way back to the AirBNB. This adventure took me to Copley Square, where I saw Trinity Church, as well as the Boston Public Library (sooo beautiful!!!! and housed some more of my new fave – John Singer Sargent. This time, it was a few of his murals).

I also had to stop and admire the Boston Marathon finish line, of course, which ends right in front of the public library. I’ve been obsessed with this race for years, and it’s on my bucket list to qualify and run it. I found the plaque celebrating the 100th year and took far too many pictures, because what can I say? Total running nerd.

Then, glowing from the running energy, I went back to the AirBNB to get changed, charge my phone, and head out for my second solo dinner: Neptune Oyster.

This experience was slightly less pleasant: I was crammed into this corner at the bar and could barely move. I felt vaguely rushed the whole time, and the door kept opening with people who entered – bringing in a frigid breeze every other minute. Definitely less pleasant.

But the food was good (oysters, shrimp, and a lobster roll, oh my!), and seafood any day makes this girl a happy girl. After, I walked over to Mikes Pastry to try a cannoli and… well, let me tell you – my life has changed forever and I’m pretty sure I’ve found a new favorite dessert. Seriously, I’m 99% positive I saw stars. Yum.

I ate my cannoli at Mike’s and when I was wrapping up, this sweet old woman came and started chatting with me. She told me all about her life, and I told her about my trip. She complimented my gloves and told me I should start a business selling them, calling it Emily’s Treasures. When I was about to leave, she wished me three blessings: health, happiness, and success. With the first two, she said, the third will find me, and then I’ll have them all.

Floating with that blessing, I went over to a local bar called the Tip Tap Room, where I met a friend and had some fried calamari, along with a few cocktails. I called it a night later than usual (almost one, my goodness!) and geared up for my second full day.


Monday started early-ish, watching the snow flurry and enjoying a light breakfast. Then, off to the MFA, where I waited in the longest line, complete with dozens of screaming kids. It’s what I get for choosing the free day, I suppose.

Once inside, I wandered at my own pace, starting with an amazing Rothko exhibit in the modern wing. He’s consistently one of my favorites, and it was wonderful to see a selection of his work all together. Then, I crossed over to the American Art wing, where I started with my favorites (Pollock, plus Motherwell and other greats from the 20th century) and worked my way back until the 1700s. I moved slowly and took my time, enjoying the work and only reading when moved – inspired from my experience at the ISGM.

The MFA has a few Pollock pieces on display, which never fail to stop me in my tracks. One particular one, No. 9, moved me to the point I had to sit, contemplate, and write in my journal. I’m pretty sure I’ll always and forever be a Pollock groupie.

I then moved back to the contemporary wing, peeking at an interesting photo exhibit about families and then a modern exhibit about resistance. Watching how art interacts with politics and culture is endlessly fascinating to me.

I wrapped up my visit with the European wing, mainly focused on the Gothic period – as well as the impressionists, a movement that has only grown on me since I first started studying art a decade ago. (I wasn’t always the biggest fa, admittedly.) I’m finding quite a bit of enchantment with Renoir’s landscapes these days.

Feeling some art overload, I headed back to the AirBNB and dressed for dinner, venturing out to a tiny (think like 15 seats, max) hole in the wall in the North End – the Daily Catch. I tried the aglio olio squid ink linguine with grilled calamari, which was out of this world. And being cash only, I feel like I really stumbled on a local place – my absolute favorite.

I ended the night early, turning in around 9 – I was so wiped from Sunday and my day at the museum! But before I could turn in, I had to put the cannoli rivalry to the test and try one from Modern Pastry. I had a chocolate chip one, and while it was good – it wasn’t Mike’s good… and I determined which side of this rivalry I fall on. (Team Mikes, all the way.)


I woke up sans alarm just after 7, a luxury I sure could get used to. I took a nice slow start to the morning, reading a few essays from the book I started on the plane, and had breakfast. Then, it was off to Fenway Park for a tour.

For all those who know me IRL, yes, I said Fenway Park and yes, I know that it’s a baseball stadium.

I’ve always been fascinated by sports, but mainly in the spectacle. And also, I’ll admit, in a bit of a jealous gosh I wish I “got it” kind of way. Every year or so, I go through a phase when I decide I should get into sports. It’s such an amazing community activity, and something that brings so many people together.

But then there’s numbers. And stats. And names and players and so many intricacies it’s difficult to keep it all straight. Not to mention, so many sports! How do you really choose?

That all being said, I gotta say – Fenway might put me at the brink of another “I should get into sports” phase. I’ve been teetering on the edge for a while, but I think it’s time. The park itself was beautiful and historic, and I loved the tour I had, where I heard all the stories and frankly, the pride, they have in their team.

So yes, me, sports. Maybe.

After getting schooled on some baseball knowledge, I made my way over to Union Oyster House to kick off my touristy afternoon. It’s so touristy and I so love it. The clam chowder was ok, but honestly – my crab cakes were amazing. One of the best things I’ve had on this trip! The bartenders were friendly, even if they were trashing Chicago – oblivious that a Chicagoan was in their midst.

With Chicago as my adopted city, I usually don’t get too defensive. But I just gotta say – real Chicagoans don’t eat deep dish. Really. I swear. At least none that I’ve ever met so shut the heck up please.

Moving on.

After my touristy lunch, I embarked on my touristy afternoon – a walk along the Freedom Trail. Which took me about 3x longer than the guidebook said it would, reaffirming something I’ve learned about myself over the course of this trip – no matter what the suggested time is, for me – I should double it. At the very least. Vacation Emily often moves in slow motion.

But as I wandered along the Freedom Trail, taking in the history, and reading from my guidebook like a nerd, I fell deeper and deeper in love with this city. (Seriously y’all, I’m head-over-heels, in way deep here.)

I’m going to have to come back in the summer, so I can do the trail with all of the stops open (most were closed for the season, or open “by appointment only”) – and I may have checked rent prices 1, 2, or like 7483782 times.

Told ya, I’m in deep.

I wrapped up the Freedom Trail at Bunker Hill, which I couldn’t climb because I got there too late (oops!), and went back to the AirBNB to charge my phone and change for dinner. I had cocktails (whiskey smash, yum!) and dinner at this place called the City Table in the Back Bay, which was good – but I’m not sure I’d highly recommend. Far better local places, in my opinion.

Turning in around midnight, it was case closed on a great third day. (And if you’ve made it this far in my rambling – I’m impressed.)


The first half of my trip has been spectacular, to say the least. I’ve met some amazing people, had some incredible food, gotten hooked on cannolis, and explored the city I’ve been obsessed with since I was 14.

I’m in the midst of my fourth day right now, and seriously wishing I’d extended my visit til Sunday when I booked – I already don’t want to leave! More to come, I’m certain. But for now – go grab a cup of water, or tea, or wine, or heck a cannoli. You’ve earned it!