To kick off November 2023, I took a weekend trip up to Boston, Massachusetts (!!!!). My cousin Sabrina and her girlfriend Nicole live in the nearby Boston suburbs and were amazing hostesses (which I am ALSO so grateful for them opening their home up to me, too!) and I got to also meet some Instagram besties of mine and have them become in real life friends (if you know, you know!). My trip to Boston was SUCH A BLESSING to me and I am OH SO GLAD that I was *finally* able to make this trip happen. The idea of me visiting Boston on my own has been in my head for … 9 years now, and I am very happy that I have been able to make it happen almost a decade later. While in Boston, I was able to see many of the sights that this New England hub has to offer, ranging from points of interest all along the Freedom Trail, Newbury Street, Beacon Hill (including the iconic Acorn Street), North End aka Little Italy, the waterfront, all the way to the Isabella Stewart Gardner Museum. My first full day in Boston, I walked 18,000+ steps and found myself crashed on the air mattress that night – LOL! Overall, I am SO happy and blessed that I was able to visit my cousin Sabrina and Nicole and have an incredible time up in New England (see snippets from my trip to New England in 2022 here, here, here, and here!).
For more United States travel inspiration, check out my Exploring 50 States expedition page.

Getting There:

Living in the Washington, DC area allows me to have MANY MANY MANY flight options for getting to and from Boston, given nearby airports and airlines. I ended up using Delta flight vouchers that I had from cancelled trips to the Carolina’s over the summer and paying $5 (!!!!!!!) out of pocket round trip out of Reagan National Airport (DCA) which is Metro-accessible for me and super close to Washington, DC. I chose to fly to Boston on a Friday evening and fly back to Washington, DC on a Monday morning, to allow for a bit of a vacation post-vacation. Over the years, I have decided to mainly stick with Delta and United Airlines (and their partner airlines) for flights, given that I have a rewards account with each and want to accumulate miles over time. The BEST PART?! Given my rewards account through Delta airlines, *somehow*, I got a free upgrade to Comfort+ heading home and found out when I went to gate check my bag which is the rows behind First Class and got to enjoy many many fun perks during my quick flight back home. I LOVED the incredible service that Delta provided on my flights both to and from Boston and look forward to flying Delta again in the future!
What I Did:

When in Boston, live as fellow Bostonians do! I REALLY enjoyed getting a taste of Boston over the weekend that I was there! The first day I was in Boston, I walked over 18,000 steps and then crashed when I got back to my cousin’s apartment – LOL! Anyhow, I LOVED getting to see SOOO many incredible sites to see here in Boston, including the many points of interest alongside the Freedom Trail, the stunning Beacon Hill neighborhood, Newbury Street, North End (including the waterfront!), and the iconic Isabella Stewart Gardner Museum. I also enjoyed getting to meet up with not one but 3 (!!!!) Bostonian Instagram besties of mine – Griffin, Timmy, and Mikayla – while in town and getting to see their incredible city from their perspectives. Truly, I LOVED getting to see Boston for the first time as an adult and learn to love this stunning, charming, and historic New England city.
While there, I mostly used public transportation via their subway system known as the T. I purchased a 1 ride or 2 ride pass which was either $2.40 or $4.80, respectively. I will note that, over time, the T has become a bit more unreliable to local Bostonians, given that the trains can be super slow and delayed, which can be an issue for those with commitments and commuting to and from work. However, the T is GREAT for not having to drive in and out of the city and around the city as well as saving on Uber/Lyft fares. Compared to Washington, DC’s Metro’s fares, the T’s fares are *pretty close* to what I pay per ride on the weekends.
Boston Public Garden





The Boston Public Garden was probably my FAVORITE spot in all of Boston (!!!!!). Indeed, it felt *just* as if I was walking through a mini Central Park …. But I was in Boston! I truly loved getting to enjoy the vibes of locals, tourists, musicians, and everyone in between in this beautiful and central spot in the city. The city skyline of Boston was also a stunning aspect of the Boston Public Garden, too! I sat on a bench in the Boston Public Garden not once, but twice, and LOVED getting to literally cool my heels and take it all in, whether it be the people-watching, crisp Fall air, or city vibes.
Beacon Hill








Beacon Hill feels like Boston’s version of Washington, DC’s Georgetown neighborhood HOWEVER it has a much much much more colonial and historical feel to it. Just like Georgetown, Beacon Hill has several shops, both locally owned and bigger known names, restaurants, cafes, and several stunning windy cobblestone streets. I popped into the stunning Beacon Hill Books & Cafe, Benefit Cosmetics, Upstairs Downstairs Home, and *of course* Starbucks. I also walked down the iconic Acorn Street – which according to my cousin Sabrina is one of the most photographed streets in the United States. Acorn Street is a historical cobblestone alley essentially that still holds its colonial charm to this very day. The best part?! I ran into my friend Joelle on a whim while wondering the streets of Beacon Hill, and I was SOOOO glad I ran into Joelle and got to see her in Boston where she’s recently relocated while on this trip!
Upstairs Downstairs Home













Acorn Street






Freedom Trail


My fellow Instagram turned in-real life (!!!!) bestie Mikayla of @blissandbows gave me a walking tour of Boston’s Freedom Trail when we met up! We walked the Boston Common to the Old City Hall (which is a favorite of mine weirdly enough!) ALLL the way to Quincy Market and Faneuil Hall. And, *of course* passing a prominent cemetery in between it all. I had a GREAT time getting to meet up with Mikayla in-person and see her incredible city from her perspective. Earlier in the day with my friends Griffin and Timmy, we walked by the Massachusetts State House, which was another super cool site to see. Boston’s Freedom Trail is spread out throughout the city yet it still somewhat centralized, too. I found it SO unique that Boston has sites from the colonial days still standing to this very day as well as tall buildings representing the big city vibe era of today.




Newbury Street

I *of course* did some shopping here on Newbury Street! Newbury Street feels like the shopping street of Boston. I popped into the stunning Lilly Pulitzer store which I had seen SO MANY photos of for many years. The ladies at the Lilly Pulitzer there were SO sweet, too! I enjoyed checking out some of the New Arrivals in-person and chatting with the Lilly ladies of Boston. Then, I headed to Kendra Scott which was such a STUNNING store and all decked out for Christmas, too, (just like Lilly Pulitzer was!!) and *of course* did a little bit of damage, getting the Emerald Elisa necklace. I truly LOVED the interiors of both Lilly Pulitzer’s and Kendra Scott’s storefronts. Like much of Boston, the storefronts of Newbury Street are in older buildings and possess such unique charm on both the interiors and exteriors.
Another neat aspect of Newbury Street was passing religious buildings of all kinds, whether a synagogue, church, or temple, that are still in use today. The biggest theme of all of these religious buildings was the fact that they all brought everyone together. Each place of worship had signs to show that they are a safe place for people of all walks of life, whether LGBTQ+, BIPOC, etc. It truly was a beautiful thing to see the love and acceptance and inclusivity in the air ALL around Boston.














North End


Mikayla and I walked ALL the way to North End from the Freedom Trail. Our first stop was the Boston Waterfront, which was STUNNING. We, then, strolled along the beautiful streets to dinner via Mikayla’s amazing recommendation of BenCotto (more on that below!). North End is known at Boston’s Little Italy neighborhood and is a very popular place for visitors and locals, alike to dine,
Isabella Stewart Gardner Museum


The Isabella Stewart Gardner Museum is probably THE BEST museum that I have ever visited, alongside the Louvre in Paris and the Uffizi Gallery in Florence (!!!!!). The Isabella Stewart Gardner Museum is actually late 1800’s-early 1900’s Boston socialite Isabella Stewart Gardner’s mansion-turned-museum. Isabella Stewart Gardner was an avid world traveler and extremely educated and bright woman for her time. Stewart Gardner learned to read and had tens of thousands of books in her collection, alongside artworks from her international travels, including to Asia, Europe, and all across the United States. Honestly, her collection of artwork and books was STUNNING (!!!!). I was truly in awe of Stewart Gardner’s collection that still prevails to this day and attracts many many many visitors year after year. I went with my cousin Sabrina and her girlfriend Nicole who both have been to the museum in the past and LOVE it. We ended up chatting with a local Bostonian who is a fellow Isabella Stewart Gardner Museum member. He ended up telling us some really neat antidotes and facts about the iconic Isabella Stewart Gardner, who had several friends at Harvard University in nearby Cambridge, Massachusetts where she was able to be inspired to pursue her lifelong passion for learning. What a woman Stewart Gardner was before her time. I left this museum feeling beyond empowered, inspired, and in awe!




















Where I Ate:

Bistro du Midi



My Instagram turned in real life (!!!!) besties Griffin and Timmy suggested that we try Bistro du Midi – a delicious French spot right alongside the Boston Public Garden – for *none other than* brunch! It was SUCH AN HONOR to be able to meet both Griffin and Timmy in-person for the first time. We had an amazing time at Bistro du Midi, too. I tried raw clams for the first time ever and enjoyed a delicious omelette with some amazing pommes frites. I also have to mention that the atmosphere at Bistro du Midi is EVERYTHING, from the bar to the second story (where we ate!) to everything in between. I also had a great time with GREAT company, too!!
Bencotto

Mikayla suggested we try Bencotto and I am SO glad that we went! Bencotto is located in Boston’s North End where Italian cuisines reign, as previously mentioned, and was such a treat. One of my highlights of Bencotto was getting to spend time with Mikayla and learn more about a restaurant that she and her family LOVE to dine at and celebrate occasions together at, too. I *surprise* got an Aperol Spritz with *none other than* a specialty pizza for dinner. Needless to say, my pizza and Aperol Spritz and pizza were well-earned and deserved after walking 18,000+ steps around town that day!
Tous Les Jours

While it is a nationwide franchise, Tous Les Jours is a favorite spot of my cousin Sabrina’s alongside her girlfriend Nicole. And, both Sabrina and Nicole take loved ones to Tous Les Jours when they come to visit them! Before Boston, I had never dined at a Tous Les Jours location and was very impressed by its unique experience. Essentially, Tous Les Jours is a French-Japanese pastry shop and cafe fusion, offering a variety of both sweet and savory pastries. Guests upon entry grab a set of tongs and can select the pastries of their choosing AND order a coffee or tea at the register when they go to pay. I got a savory quiche and a sweet chocolate-filled croissant alongside a pumpkin spice latte!
Pressed Cafe
After wondering and being in literal heaven at the Isabella Stewart Gardner Museum, Sabrina, Nicole, and I headed to Pressed Cafe located at Prudential Center. A New England/Northern-based breakfast and Mediterranean like cafe chain, Pressed Cafe was SO gorgeous on the inside and offered something literally for everyone! I definitely enjoyed the vibes at Pressed Cafe and the market-like array of goods such as hummus and freshly pressed juices for guests to purchase and take home with them. Pressed Cafe was definitely a unique spot that I would try again when in New England!
Wrap-Up:

Overall, I LOVED getting to *finally* visit Boston as an adult. The last time I went to Boston before this trip was when I was 15 and couldn’t really go off on my own and do my own thing. And, since that trip as a 15 year old, I had been wanting to go back to Boston and do *none other than* my own thing on a trip there. I am SO glad I got to do my own thing on this trip … a whopping 9 years later! This trip, I got to explore the stunning Beacon Hill neighborhood, shop and browse the gorgeous stores there at my own pace, explore the historic sites to see alongside the Freedom Trail, and visit a new-to-me museum that I fell IN LOVE with.
At the same time, I am SO SO SO grateful to have many loved ones in Boston, including my cousin Sabrina and her girlfriend Nicole who were incredible hosts during this trip. I LOVED getting to finally meet my Instagram friends Griffin, Timmy, and Mikayla and have them become in real life friends. Needless to say, I feel SOOO much gratitude for this trip and to be able to fall in love with another place in New England (growing up I spent summers up in Maine!). I ALSO am so so so excited for visiting Boston and other parts of New England in the future, as I have some friends in Boston and Newport, Rhode Island that I have yet to meet up with in their respective homes. New England is probably my favorite place in the world, given its charm and stunning coastlines to mountainous skylines. Moving forward, I aspire to visit New England at least once a year!
XOXO – Katie <3





























































