Boston Bucket List: What I Loved (and What Went Wrong!)

Boston has been on my travel bucket list for the longest time, people always ask me why, and it’s because contrary to popular belief, I’m a true nerd at heart. I love cities rich with history, reading, and just exploring new cities. Boston has all of that and more, and I’m beyond grateful that I finally got the chance to visit! Even better, I was able to go for a work trip, so it was truly a blessing. God is so good, and He continues to open doors for me in ways I can’t even imagine.

But…no trip is perfect, and let me tell y’all… I had a few hiccups along the way. Between a HORRIBLE hotel experience and a hair appointment disaster, I had to pivot real quick! But despite all that, Boston absolutely stole my heart.

I flew in Friday night on a red-eye so I could enjoy the weekend before jumping into work mode on Monday. I was exhausted and definitely slept in both days, but I still managed to see some of the best parts of the city. My coworkers have already convinced me to come back in the summer when it’s not FREEZING—an offer I just might take them up on.

I didn’t get to do everything on my itinerary, which just gives me even more reason to return (and seeing the Red Sox play at Fenway is still on my bucket list!). Here’s how my Boston weekend went:

Saturday: Exploring the Heart of Boston

11:00 AM – Breakfast at Tatte Bakery & Café (Beacon Hill)

I started my morning at Tatte Bakery & Café, a cozy spot in Beacon Hill. Their pastries are top-tier, and the pistachio latte? Perfection. I grabbed a latte and soaked in the cute atmosphere before heading out for a day of exploring.

1:00 PM – Lunch at Row 34 (Seaport)

Next up was Row 34, one of Boston’s best seafood spots. I had the caviar oysters, a lobster rol, paired with an Aperol Spritz (which is the first one I had in the states that tasted the same as the ones I had in Italy). The oysters were fresh, the lobster roll was buttery perfection, and the whole vibe of the restaurant was just right.

3:00 PM – Exploring the Boston Public Market & Quincy Market

I love checking out local markets when I travel, so Boston Public Market & Quincy Market were perfect for grabbing snacks and seeing all the local vendors. I shopped around at Sephora and found a nail bar to get my eyebrows waxed. It was a perfect day of sight seeing and I ran into a few random, but hilarious street shows.

5:30 PM – The Hair Appointment from Hell

Okay, this is where things went ALL the way left. I booked a hair appointment from a stylist that I’ve had on my bucket list for the last TWO years. The hair appointment cost a COIN, but you know, girl math – everything else was going to be covered by my job, so why not? For some reason, I typically have a terrible experience at hair appointments, either they’re running late, unprofessional, or simply lack customer service, but this horror was ALL THREE.

I arrived five minutes early but couldn’t find the salon (first red flag). The appointment confirmation didn’t include a contact number, so I was going off a hope and a prayer. When I finally found a landline number (who even has those anymore?!), I called, and both the stylist and her assistant were beyond rude.

When I finally got inside, she was silent the entire time. Which—fine, not everyone is social. But for the price tag, you’d think customer service would be included, right? WRONG. She was also running 30 minutes behind, and when I finally sat down, she realized my hair wasn’t washed.

Her reaction? Pure annoyance.

Me? Confused. Because why was a $35 wash not included in a luxury-priced appointment? And why wasn’t I given the option to add one beforehand?

The energy was off the entire time, and I even had to ask her if she was okay. If I wasn’t in town for a major business meeting, I would’ve walked out. But I needed my hair done, so I powered through.

When I finally left, I was traumatized. The stylist was unprofessional, the service was trash, but at least my hair looked good (I guess). One thing’s for sure—she will never see me again!

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11:00 PM Relax & Unwind

After the horrific hair experience, I just needed to relax, I had plans to go to dinner at Comfort Kitchen, a Black-owned restaurant at 10:00 PM, but since my hair appointment ended later than expected, I decided to go for brunch the next day and ordered tacos from Borrachito to my room (and they were SOO good).

Sunday: Harvard, Art, and Rooftop Views

1:30 PM – Brunch at Comfort Kitchen (Dorchester)

After my hair fiasco, I needed some GOOD energy, so I went to Comfort Kitchen, a Black-owned restaurant in Dorchester serving up global flavors inspired by the African diaspora. The food was amazing, and the atmosphere was so warm and welcoming—exactly what I needed to lift my spirits.

3:30 PM – Museum of Fine Arts

The art collection is massive, and because I was short on time I could only see one exhibit which was “Exploring The Early Americas”, now if you know anything about the history of Boston, you know it doesn’t have the best reputation for how it represents African-Americans, and let’s just say this exhibition made that clear.

As I walked around I became angry because every other culture had entire rooms dedicated to them, their history, and their impact to building early America. Pictures of us did not showcase our true history and only showcased renditions of us in a “futuristic” way, ignoring the horror of what it meant to be an African American in early America.

They skipped past all of the bad things, all the things that make us, US, and dedicated a “jazz room” to us, which is clearly not a clear rendition of early America. Major miss by the MFA.

5:00 PM – Harvard University Visit (Cambridge)

Harvard has been on my list forever, so I was excited to finally visit! I walked around Harvard Yard, and explored the Harvard Book Store. The temperatures were dropping and I was not well prepared, I had layers and a leather coat on but I definitely needed something to cover my head and a bubble coat. I would go back to visit with a guided tour, because I must say the campus was extremely…underwhelming.

I headed back to my room to get ready for dinner at Ostra.

7:45 PM – Dinner at Ostra (Back Bay)

My last meal in Boston was at Ostra, a sleek seafood restaurant with Mediterranean flavors. Everything was beautifully plated and tasted just as good as it looked. I met with a coworker and we hit it off right away, I had oysters once again and boy were they so good. The rep that Boston gets for is seafood is well deserving.

Monday: All Work & Some Play

On Monday, I was back in work mode, but my coworkers had the chance to enjoy dinner at Yvonne’s, a stylish supper club known for its amazing craft cocktails—I highly recommend it! The menu is designed for sharing, so we ordered a little bit of everything. The oysters (of course), pork, and lobster dumplings were standouts, but honestly, everything was delicious!

The Hotel Situation: From Nightmare to Dream Stay

Now, let’s talk about my hotel situation…

I originally booked The Moxy, and let’s just say it was a BIG mistake. The stay was absolutely horrible—the rooms were tiny, the service was disappointing, and the whole experience just wasn’t it.

Thankfully, I made a last-minute switch to The Lofton Hotel, and WOW. The difference was night and day! The service was top-tier, the rooms were beautiful, and I felt so comfortable and welcomed. If you’re ever in Boston, I highly recommend staying there!

There were a few things I didn’t get a chance to do, which I’ll definitely keep on my itinerary for when I come back (when the temperatures are warmer).

Boston Public Library (Copley Square)

Y’all… this was one thing on the itinerary that I’ did not get to do and I am’m most upset about missing, I thought I would be able to go once the work week started but there was simply not enough time.

Sunset Drinks at Lookout Rooftop (Seaport)

The views of the city and waterfront looked so beautiful, but I still had a chance to visit the Seaport area when I went to Row34.

Isabella Stewart Gardner Museum

I skipped this due to the weather and time constraints, but the Venetian-style architecture and the incredible art collection is definitely something worth coming back for.

Walking the Freedom Trail

This 2.5-mile route takes you through some of the most historic sites, like Paul Revere’s House and Faneuil Hall. I made it to the Boston Common but by the time I got here, I was freezing and knew it would not be a pleasant experience, so I decided to table this for the next time. But it’s a MUST SEE if you visit Boston!

Final Thoughts

Despite the setbacks (looking at you, hair appointment and The Moxy), Boston was an unforgettable experience. The food, the history, the energy—I loved just about every second of it. I’m so thankful for the opportunity to travel for work, and I know this won’t be my last time in this amazing city.

Until next time, Boston! 💛

Would you visit Boston? Let me know in the comments!