Travel Tuesday with Taylor to Boston, Massachusetts

Posted on Social Impact, Travels with Taylor November 21, 2017 by Taylor Deer

A Girl Cousin’s Getaway

by Taylor Deer

Happy Almost Thanksgiving! As I ponder over what I am grateful for, one of the many things that come to my mind are all of the adventures I went on over the past year. A lot of my trips were planned ahead, some of them came un-expectantly with work and most of them were planned last minute like my recent weekend getaway to Boston with my cousin Alexie (of Travels with Lexy).

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Although I was born and raised in the Northeast, I had never been to Boston before. As many of you question why, since I have traveled to places much further, it is mainly because I always thought of it as a small boring Colonial city with not much culture. One of the things I have been working on lately is to stop assuming things about a certain place. Just like my trip to Ireland last month, Boston exceeded my expectations for a weekend getaway!

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This quaint US city is filled with charming neighborhoods, amazing restaurants, fun bars, beautiful parks and a lot of history. Alexie and I decided to do a quick trip right before the Thanksgiving/Black Friday rush to check it out and enjoy a girl cousins’ weekend getaway.

Even though summertime is the best time to visit New England, the fall season is too beautiful to miss out on. I was so excited to visit Boston and see the beautiful fall colors right before they diminish. Since I am from the New York City area, I decided to drive up to Boston (it takes a little over 3 and a half hours without traffic). Because Alexie is from the Miami area, she flew to Boston and we met up on Friday night to begin a fun-filled weekend!

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The hotel we stayed at in Boston was AWESOME! The Liberty Hotel is located in Beacon Hill, which was my favorite area in the city. Before it became a luxury hotel, The Liberty Hotel was the Charles Street Jail. The jail was completed in 1851 and operated for over 120 years.

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From 1851 through 1973, the prison housed some of Boston’s most notorious criminals. The prisoners later revolted because of poor living conditions and the jail ended up being declared unfit as it violated their constitutional rights. On Memorial Day weekend in 1990, the last prisoners were moved to the new Suffolk County Jail.

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In the early 2000s, the old jail was remodeled into a beautiful and innovative hotel. Apart from renovating the building, the jail’s granite exterior and expansive interiors remain unchanged. The jail cells and wrought-iron gates featured within the hotel lobby, restaurant and bar are examples of preservation. It was so cool staying in an old jail! Plus, the place was rocking with millennials who were looking for a fun night out, corporate employees enjoying a happy hour and travelers from all over the globe enjoying Boston’s historical culture. When I arrived on Friday night, I was exhausted, but once I entered into the hotel, my energy soared. There was so much excitement going on around me that I couldn’t wait to unpack in my hotel room and join in on the fun!

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Since my cousin went to school in Boston, she had a few of her friends meet us at the hotel to enjoy the night. Before we started the party, we got an amazing burrata, truffle and arugula pizza at Liberty Bar. The bar was so much fun, so we stayed there for a little bit before heading to the dance bar on the first floor called Alibi. Set in the old “drunk tank” of the jail, Alibi features original brick cell walls. There are also celebrity mug shots scattered along the walls of the bar. Some of the celebrities we saw were Jay-Z, Lindsay Lohan, Justin Bieber and Matthew McConaughey. These celebrities weren’t inmates in this specific jail, but it was interesting to see their mug shots.

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We had a blast dancing all night long and meeting new people. When I got back to the hotel, I enjoyed one of the best sleeps I had in so long. The next morning, I could not wait to enjoy brunch! I LOVE brunch, especially on a girl’s weekend getaway and it has been forever since I enjoyed one.

Since the hotel had so many great places within it, we decided to have brunch at a cool restaurant called Clink. The restaurant features restored jail details and architecture, but have big windows that let the sunlight shine in. I enjoyed one of the best brioche French toast dishes with Canadian maple syrup and Vermont maple sausage on the side. Alexie had the smoked chicken quesadilla. Even though I am not a Bloody Mary fan, I thought it was awesome that the restaurant had a DIY bar to make your own! Alexie took advantage of it.

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After our amazing brunch, we were ready to take on Boston! Since the hotel is located in the most charming area of the city, we were excited to start exploring Beacon Hill. Featuring beautiful Federal-style houses, Beacon Hill is known for its narrow, gas lit streets and brick sidewalks. It is regarded as one of the most desirable and expensive neighborhoods in Boston and I could tell it was right when I stepped out of the hotel.

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We were lucky because the weather wasn’t as cold as we expected it to be, but it was still a little chilly, so we stopped in a cute coffee shop called Peet’s Coffee to pick up a nice peppermint-mocha to warm ourselves up as we continued to explore more. The cool thing about Peet’s is that you can find them in various locations throughout the city.

As we continued to wander around Beacon Hill, we stopped at another gem called Rouvalis Flowers. This welcoming corner shop offers a warm feeling right when you walk in. The smell of fresh flowers and pines (for the season) filled the air! There were also a variety of different home good pieces, ornaments, coffee mugs and more. It was lovely!

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We eventually made our way over to the Boston Public Garden, which is adjacent to the famous Boston Common. This lovely park has different walking paths, beautiful Spanish moss trees, adorable animals and a pretty bridge that goes over a little pond. It was nice to walk around and see some nature within the city.

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Right across the street from the Public Garden is the iconic Cheers Bar from the Nick At Nite sitcom, Cheers! I remember watching Cheers at night when I was in Elementary School and finding their accents amusing. Of course this bar was on my bucket list and I thought it was funny that we just stumbled upon it un-expectantly rather than searching the entire city for it.

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The Cheers Bar is actually bigger than what you could imagine. There are three rooms in the place: the original bar where they shot the sitcom, a restaurant area and another bar that overlooks the park. There are several gift shops in the bar and it is even attached to a beautiful hotel! My cousin and I enjoyed a beer in Cheers’ famous glass mugs.

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Since we were in New England, it was only right that we got a lobster roll – my all-time favorite seafood lunch item! Prior to going to Boston, I was recommended a delicious lobster roll place in the North End area called Pauli’s. You can choose between a hot and buttery lobster roll or a cold mayo roll. I personally am not a mayo fan, so I chose the hot one, while Alexie got the cold lobster roll. In addition to lobster, you can also get Italian sandwiches, salads, burgers, wraps and more! Pauli’s is a fun place, but it gets crowded and there isn’t much seating room. They have a barstool by the wall where you can stand and eat, but Alexie and I decided to take our lobster rolls outside and people watch. One thing I learned about Boston is that the people aren’t as interesting as they are in NYC.

After our fulfilling lobster roll, we decided to head back to the hotel to relax, nap, watch Christmas movies and get ready for the night. Since Alexie and I grew up spending Christmases together, it was awesome to relax and pretend like we were back at my nana’s old house.

Later in the evening, we decided that we wanted to enjoy Italian food since Boston has a renowned “Little Italy” area. Located in the Faneuil Hall district are numerous Italian restaurants, bakeries and cafes to enjoy a delicious meal or treat. I was recommended to check out Dolce Vita Ristorante on Hanover Street. The owner, Franco Graceffa, was super friendly and welcoming as we stepped into his restaurant. The restaurant is spacious with a lot of seating and there is even a wine bar area if you want to enjoy antipasti or light appetizers.

The meals we had at Dolce Vita Ristorante were out of this world! I had the special, which was fettuccine with jumbo shrimp and scallops in a white wine tomato sauce with fresh sundried tomatoes. (My mouth is watering as I think about it.) Alexie had a delicious gnocchi dish in a vodka sauce. We were definitely satisfied!

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Since we had a late dinner, we went out straight from there. Located in the Fort Point area is a craft cocktail bar called Drink that blends classic cocktails of the prohibition era with modern artisanal ingredients. My friend Courtney who goes to Boston quite often recommended this great speakeasy to me! (Thanks Court!)

Drink is a hotspot in Boston, so there was a line to get into the bar area. We only had to wait 15 minutes and once we got in, I fell in love with the atmosphere. It was the perfect place to enjoy a drink crafted just for you! That’s right, the bartenders at Drink are pros at making the best craft cocktails based on your preferences. After you find a seat, a bartender will make his or her way over to you and ask you what flavors you like in a cocktail. Since I like my cocktails more sweet than strong, I told our bartender that I like anything maple syrup-related, molasses and rum. In addition, Alexie loves spices, so he made the perfect drink for both of us. I definitely recommend visiting this place if you are in the Boston area.

Both Alexie and I were sad when we knew we had to leave the next day. Even though it was our last day, we were going to make the best of it! I was dying to try the famous Mike’s Pastry, but it was too far and we didn’t want to waste time going to the other side of town. I’ll admit though, I highly regret not going there because I heard it is amazing!

We were craving a nice brunch again, so we found a great place right near our hotel called the Tip Tap Room. This great American bar features an open space and delicious food and drinks. Both Alexie and I enjoyed the smoked salmon omelet with their delicious coffee. I had a mimosa along with that and Alexie had a Bloody Mary again. It was delicious.

After we checked out of our hotel, we wanted to check out the famous Samuel Adams Brewery, since it is one of my favorite beer brands, but were disappointed when we found out it was closed on Sundays. Instead, we made our way over to Harpoon Brewery, located in South Boston on the Boston Main Channel. This ended up working out since it was close to Boston’s Logan Airport, where I had to drop Alexie off afterwards.

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Harpoon Brewery is a lively and fun bier hall that features delicious beers straight from the source along with a freshly, baked pretzel. We got the UFO flight, which consisted of coffee, vanilla bean and fruity-flavored beers. We also enjoyed the views of the water from the brewery. It was the perfect way to end our weekend getaway in Boston.

I hope you all enjoyed my blog post on my cousins’ weekend getaway in Boston. If you are looking for a quick getaway or a four-day weekend trip, you can experience the fun we had by having us book it for you! Email me at or call us for more information.

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Happy Travels!


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2 responses to “Travel Tuesday with Taylor to Boston, Massachusetts”

    America's Best Foodie Spots

    May 8, 2018

    […] Click here to read my blog post on Boston and book your trip today. […]

    The Best Destinations to Travel with Your Mom

    May 1, 2018

    […] and hotels like The Liberty Hotel; famous and iconic bars such as Cheers and beautiful parks. Click here to read my blog post on […]

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