23755562_10155876287232640_5245508374282114067_n

Fall foliage in Boston

Boston, Massachusetts is a beautiful city that cannot be missed when visiting the East Coast of the United States. In fact, Boston makes for the perfect girls weekend getaway and I cannot wait to show you why!

The city of Boston is the capital of Massachusetts and it was named after a town in England. It’s one of the most popular and abundant cities in the USA and the city was also home to the Boston Tea Party in the late 1700s. Nowadays, this quaint U.S. city is located in New England and is filled with charming neighborhoods, amazing restaurants, fun bars, beautiful parks and a lot of history. It’s the perfect place to visit in the fall!

Stroll through Beacon Hill during a girls weekend in Boston

During fall 2017, my cousin and I visited New England for a well-needed girls weekend in Boston and we ended up having the time of our lives! (I also revisited Boston with a friend during autumn 2020.) Overall, Boston makes for one of the best fall vacations on the east coast!

In addition, visiting New England during autumn is a beautiful site to see since the colors of fall foliage are in full swing. When planning a fall getaway, you cannot do wrong with anywhere in New England. If you’re looking for a fall weekend trip from Boston, visiting destinations like Salem, the White Mountains of New Hampshire, Woodstock, Vermont and the Berkshires will not leave you disappointed.

In this article, discover the best things to do during a girls weekend getaway in Boston.

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like.


Pin the Below Image to Keep Handy

A Weekend in Boston

Planning a Trip to Boston:

Beacon Hill during a girls weekend in Boston

Since Boston is a larger city, you can easily travel there from anywhere in the world by taking a flight into Boston Logan International Airport. You can find affordable flights through Skyscanner!

Other ways to get to Boston are through public transportation. The Amtrak train runs from major U.S. cities like New York, Philadelphia and Washington D.C. and takes passengers to Boston every day! If you’re coming from the New York City area, like I did, you can either drive to Boston or take a Flixbus.

From the New York area, it is around a 3.5-hour drive to get to Boston, depending on traffic. From Philadelphia, it takes 5 hours to get to this stunning city and from Washington D.C., it takes over 7 hours to get to “Beantown”. If you decide to drive to Boston and either don’t want to put miles on your vehicle or even if you do not have a car of your own, it is best to rent one.

For those who fly into Boston, the best way to get from the airport to your accommodation is via a taxi or ride sharing app like Uber or Lyft. Another way to get to your hotel is through Go Airport Shuttle!

Looking for an RV for your next trip, reserve here!

Where to Stay in Boston for a Girls Weekend:

A woman at the Liberty Hotel in Boston

Thanks to Crawford Concierge, the hotel that my cousin and I stayed at during fall 2017 was EPIC! They helped us plan the perfect girlfriends guide to Boston!

The Liberty Hotel is located in Beacon Hill, which is 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.

From 1851 through 1973, the jail 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 in 1990, the last prisoners were moved to the new Suffolk County Jail. In the early 2000s, the old jail was remodeled into a beautiful, luxury and innovative hotel. Apart from renovating the building, the jail’s granite exterior and expansive interiors remained unchanged.

The jail cells were wrought-iron gates that were featured within the hotel lobby, restaurant and bar. They are examples of preservation! It was cool staying in an old jail during this fun girls weekend in Boston! Plus, the place was rocking with people having a good time.

In addition to The Liberty Hotel, you could find numerous hotels to suit your budget in Boston. There is also a variety of rental options that make for great places to stay in Boston!

Best Places to Stay in Boston:

Luxury: Fairmont Copley Plaza (I stayed here my second time in Boston in 2020.)

Boutique: Kimpton Nine Zero Boston

Mid-Budget: Boston Marriott Long Wharf

Budget: HI Boston Hostel

Food and Entertainment in The Liberty Hotel:

Staying at the Liberty Hotels during a girls weekend in Boston

Liberty Bar: Before my cousin and I enjoyed our first night “out” in the hotel, we savored an amazing burrata, truffle and arugula pizza at Liberty Bar. (It was amazing!)

This bar is a great place to casually grab food and drinks in the hotel. It is also the perfect spot for an afterwork drink! I say it like that because happy hour bars are actually illegal in the city of Boston.

A mug shot of Lindsay Lohan at the Liberty Hotel

Alibi: For some late night dancing and fun, my cousin and I went to 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. We had such a blast dancing and meeting new friends at Alibi.

Staying at the Liberty Hotel in Boston during a girls weekend

Clink: During a girls weekend in Boston, it is obligatory to get brunch! Since The Liberty Hotel had so many great places to eat, 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.

During my first trip to Boston in 2017, I enjoyed one of the best brioche French toast dishes with Canadian maple syrup and Vermont maple sausage on the side. My cousin had the smoked chicken quesadilla. (I had an omelet during my second Boston girls weekend in 2020.)

Brunch during a girls weekend in Boston

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! My cousin took advantage of it while I had a mimosa.

In addition to the above, The Liberty Hotel also has another fine dining Italian restaurant called Scampo, an outdoor venue called The Yard, an upscale bar called Catwalk and they also have great room service.

Where to Eat and Drink during a 3-Day Boston Itinerary:

Two women enjoying at drink at a speakeasy during a girls trip in Boston

Pauli’s: Since we were in New England, it was only right that my cousin and I get a lobster roll during our weekend Boston trip in 2017.

Prior to going to Boston, I was recommended a delicious lobster roll joint in the North End area called Pauli’s. You can choose between a hot and buttery lobster roll (Connecticut roll) or a cold mayo roll (Maine roll). I got the Connecticut roll and my cousin got the Maine roll.

In addition to lobster, you can also get Italian sandwiches, salads, burgers, wraps and more! Pauli’s is a great place, but it gets crowded and there isn’t much seating room.

Dolce Vita Ristorante: During our girls weekend trip in Boston, 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 cafés to enjoy a delicious meal or treat. We were recommended to check out Dolce Vita Ristorante on Hanover Street.

The owner, Franco Graceffa, was friendly and welcoming as we stepped into his restaurant. The restaurant itself is spacious with a lot of seating and there is even a wine bar if you wish to enjoy antipasti or light appetizers.

For my main meal, I savored fettuccine with jumbo shrimp and scallops in a white wine tomato sauce with fresh sun dried tomatoes. Alexie had a delicious gnocchi dish in a vodka sauce.

An Italian dinner from La Dolce Vita in Boston

Drink: Located in the Fort Point area of Boston is a speakeasy bar called Drink that blends classic cocktails of the prohibition era with modern artisanal ingredients. It is one of the best spots to have fun in Boston this weekend and beyond!

Drink is a hotspot in Boston, so there was a line to get into the bar area (when I visited in 2017). At the time, we only had to wait 15 minutes and once we got in, I fell in love with the atmosphere.

Overall, 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 what flavors you like in a cocktail. In 2017, I liked my cocktails more sweet and not strong, I told our bartender that I enjoy anything maple syrup-related, molasses and rum. In addition, Alexie loves spices, so he made the perfect drink for both of us. I couldn’t recommend this place more! (Next time, I’d love to try their smokey cocktails.)

State Street Provisions: During my second girls weekend trip to Boston in 2020, my friend and I enjoyed a lovely dinner at the rustic and contemporary restaurant of State Street Provisions in the Long Wharf area.

I loved the ambiance at State Street Provisions and during our evening, I savored a delicious Angry Queen Pizza (which was a Margherita pie) with a fall sangria. My friend had the steak frites with a sangria too. Everything was amazing!

Pizza from State Street Provisions in Boston

Mike’s Pastry: Located in Boston’s North End along with Cambridge, Somerville and TD Garden, Mike’s Pastry was founded in 1946 and it’s known as one of the best Italian pastry shops in the city.

Owner Michael Mercogliano created a one-of-a-kind cannoli that keeps locals and tourists coming back for more. It is at this amazing pastry shop where you could get cannoli and pastries, Italian cookies, pies, cakes and gelato. It is a MUST if you are visiting Boston!

I unfortunately didn’t make it to Mike’s Pastry with my cousin in 2017, but my friend and I visited the Cambridge location in 2020. I got the Nutella cannoli, which was amazing and my friend got the lobster tail, which she also enjoyed!

The Best Itinerary for a Girls Weekend in Boston:

Wander through Beacon Hill:

A woman sitting on a stoop in Beacon Hill during a girls weekend getaway in Boston

A girls weekend in Boston would not be complete without getting lost in Beacon Hill, the city’s most charming area.

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.

Discover 5 misconceptions and 5 truths about life in Boston!

A beautiful building in Beacon Hill of Boston

I mainly got to explore Beacon Hill during my getaway in 2017 because I had more time, but I also had the opportunity to walk through a piece of it during my shorter time in Boston in fall 2020. It’s one of the best places to explore during your girls weekend in Massachusetts!

Overall, my cousin and I were lucky when we visited in 2017 because the weather wasn’t as cold as we expected it to be, but we still kept extra warm by visiting the cute coffee shops in Beacon Hill.

Rouvalis Flowers in Boston, Massachusetts

As we continued to wander around Beacon Hill, we stopped at another gem called Rouvalis Flowers. This lovely corner shop offers a warm and welcoming feeling right from the moment 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.

Walk through Boston Public Garden and Boston Common:

A woman strolling through Boston Public Garden

Two great places to walk around in the city during fall trips in Boston are the Boston Public Garden and the Boston Common.

The Boston Common is a 50-acre urban park that hosted the British troops during the American Revolution.

The Boston Public Garden, on the other hand, has different walking paths, beautiful Spanish moss trees, adorable animals and a lovely bridge that goes over a little pond. They are both romantic places in Boston to stroll around and admire beautiful nature.

Make a Visit to the Cheers Bar:

The Cheers Bar in Boston, Massachusetts during a girls weekend

Right across the street from the Public Garden is the iconic Cheers Bar from the Nick At Nite sitcom, Cheers!

I used to always watch Cheers at night when I was in elementary school, so of course the bar was on my bucket list and I thought it was funny that we just stumbled upon it unexpectantly rather than searching the entire city for it.

The Cheers Bar is actually bigger than what you could imagine! It’s a fun experience to add to your Boston itinerary.

A woman enjoying a beer during a Boston girls weekend

There are three rooms at the Cheers Bar: 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!

Visit the Paul Revere House:

If you are big history person, then you will totally love Boston! There are so many memorable and crazy things to do in Boston to learn all about the city’s past.

Since my cousin and I were only in Boston for a short, girls weekend, we didn’t have the time to see all of the historical sites. One place you must see is the Paul Revere House. Built in 1680, this colonial building was home to the American patriot Paul Revere during the Revolution.

Shop Your Way through Newbury Street:

Go shopping on Newbury Street during fall in Boston

If you are a big shopper, then you definitely have to head to Newbury Street during a girls trip, which is located in the Back Bay area of Boston.

It is on Newbury Street where you could find fashion stores, consignment shops, restaurants, coffee shops, hotels, beauty salons, bars, art galleries, tourism offices and so much more!

Stroll around Boston Harbor:

Enjoy the Boston Harbor during a girls weekend in Boston

Known as the site of the Boston Tea Party, Boston Harbor is a peaceful place to stroll around and admire the beauty of the city.

The Boston Tea Party took place on December 16, 1773 when members of the Sons of Liberty dumped crates of tea into the Boston Harbor as a way to protest against the Tea Act and its provisions for taxation of tea. Nowadays, it is home to the Port of Boston, which is a major shipping facility in the Northeast.

Overall, Boston Harbor is a beautiful area to walk around, admire a sunset and relax at. It’s one of the best vacation spots in Boston, Massachusetts!

Attend a Sporting Event during your 2 Days in Boston Itinerary:

Seeing a New England Patriot's game during a girls weekend in Boston

Whether you’re visiting Boston in fall, when the New England Patriots are playing, or in the spring, when the Boston Red Sox play, I highly recommend attending a sporting event because the spirit in the city is unreal.

Fenway Park (where the Red Sox play) is a great place to visit year round since concerts are also held there.

Enjoy an Afternoon at a Boston Brewery:

A woman drinking a beer at Harpoon Brewery in Boston during a girls weekend

Samuel Adams Brewery: Known as Boston’s most famous lager, Samuel Adams is a must-visit when you’re in the city during a girls weekend.

Please note though that the brewery is closed on Sundays. Unfortunately, my cousin and I didn’t get a chance to go in 2017 since we didn’t know that originally.

Each year, beer enthusiasts at Sam Adams travel to Germany to select the world’s best heirloom aroma hops for their lager!

Harpoon Brewery: Since Sam Adams was closed, my cousin and I made our way to Harpoon Brewery, located in South Boston on the Boston Main Channel. Spending a day at this spot makes for one of the best girls weekend activities!

Harpoon Brewery is a lively and fun bier hall that features renowned beers straight from the source along with German and American food.

We both 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.

A craft beer flight from Cambridge Brewing during a girls weekend in Boston

Cambridge Brewing Co.: During my trip to Boston in 2020, my friend and I decided to check out the Cambridge area (including Harvard University) and had lunch at Cambridge Brewing Co.

Located in Kendall Square, Cambridge Brewing Co. is the oldest brewpub in the Greater Boston area and it offers flavor-forward beers using only water, malt, hops and yeast.

My friend and I had lunch at this great spot and enjoyed a flight of four delicious beers. I had the Cambridge Amber, which is an American Amber; The Great Pumpkin Ale, which is made with local pumpkins; I Remember My First Check-in, which is a kettle sour gruit and Heather Ale, which is an unhopped herbal ale.

For lunch, I savored the delicious fried chicken sandwich with fries and my friend had the buffalo chicken tenders that also came with fries. Everything was delicious!


Other trips you must take with your girlfriends:

7-Day New England Fall Road Trip Itinerary

A Perfect Girl’s Getaway at Woolverton Inn

Best Girl Trip Destinations in the World

I hope you all enjoyed reading about the best things to do during a girls weekend in Boston, Massachusetts. If you have any questions about my time in Boston, please email me at info@browneyedflowerchild.com.

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., MA State Capital: Boston, Time Zone: Eastern Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my Boston look:

Click here to shop my Poshmark closet!

Related posts

What to Eat at German Christmas Markets

A trip to Germany in December is not complete without visiting the Christmas markets (or Christkindlmarkts) that pop up in...
check out the post

A Day Trip to Hallstatt from Salzburg

Known as one of the most photographed destinations in the world, Hallstatt, Austria is a magical place to visit during...
check out the post

Warm Places to Visit in November

November is one of the best times to enjoy a great trip before the start of the holiday season. From...
check out the post

32 Comments

  1. Merrie Rodriguez on August 19, 2019 at 8:11 am

    My husband and I have really been wanting to head to Boston for the longest time! Hopefully we can get there soon!

    • Taylor Deer on August 19, 2019 at 12:03 pm

      It’s a great city and I highly recommend it for the fall! 🙂

  2. Courtney Delfino on August 19, 2019 at 2:34 pm

    My favorite part of Boston is for sure Boston Common! Such a beautiful park! Great read Taylor!

    • Taylor Deer on August 19, 2019 at 3:56 pm

      Yes, I loved the Spanish moss they had. It was so lovely!

  3. Josefine on August 19, 2019 at 3:28 pm

    I’ve been wanting to go to Boston for the longest time! I’d love to see the leaves during fall some time ? it looks like you had a great time there! And the photo of Boston from above is crazy beautiful!!

    • Taylor Deer on August 19, 2019 at 3:57 pm

      You definitely have to make your way to the Northeast of the United States during the fall season. It is so beautiful and you would love it! 🙂

  4. Zsuzsanna Paluska on August 20, 2019 at 9:52 am

    Such a nice trio, loved to read your experiences! Boston sounds like a perfect city for a weekend getaway! It’s our dream to visit the US one day, we can include Boston in our itinerary ?

    • Taylor Deer on August 20, 2019 at 12:24 pm

      Thank you so much Zsuzsanna! I highly recommend to visit Boston during the fall season. It is so beautiful! 🙂

  5. World of Lina on August 22, 2019 at 5:12 am

    I don’t know why but I have the feeling I would totally love Boston! Looking at your photos makes me wanna book a flight there immediately ☺️

    • Taylor Deer on August 22, 2019 at 8:49 am

      Yes, I loved it so much when I went almost two years ago. My cousin and I had such a blast and I totally recommend going in the fall! 🙂

  6. Bucketlist Bri on August 22, 2019 at 4:42 pm

    Aww another beautiful blog post, Tay! Ya know I just went through Portland, Maine the other day and thought of you. Shame we didn’t make it to Boston!

    • Taylor Deer on August 24, 2019 at 4:45 am

      Thank you so much Bri! Ah I hope you enjoyed Portland. Next time you have to make it to Boston! 🙂

  7. Francesca on November 2, 2020 at 12:08 pm

    I love Boston! It would be such a fun place for a girls weekend! The Samuel Adams Brewery was so fun. I also love wandering around the Boston Common and Public Gardens.

    • Taylor Deer on November 2, 2020 at 11:20 pm

      It really is a beautiful city! This recent trip was my second time in Boston and I fell in love with it even more! 🙂

  8. Katiesaway on November 4, 2020 at 8:34 am

    I love it in Boston! My uncle moved there a few years ago so we have been to visit a few times! Such a beautiful and calm city

    • Taylor Deer on November 4, 2020 at 9:41 am

      It really is a stunning city! I want to go back and see more. 🙂

  9. Megan on November 14, 2020 at 12:26 pm

    oh my goodness that is SO cool you could see the Cheers bar! What a cool stop!

    • Taylor Deer on November 14, 2020 at 5:45 pm

      Yes, it was a fun place! Much bigger than I would’ve imagined though. 🙂

  10. Jamie on November 14, 2020 at 4:30 pm

    Boston has so many great breweries, and the Public Gardens are my favorite!

    • Taylor Deer on November 14, 2020 at 5:47 pm

      Yes, I loved them all, especially Cambridge! 🙂

  11. Krista on November 14, 2020 at 6:07 pm

    These are some great places to visit in Boston for a weekend away! Adding some of these stops to my list for when I visit the city.

    • Taylor Deer on November 15, 2020 at 9:58 am

      Yes, I love Boston so much! It is such a beautiful city! 🙂

  12. Rebecca on November 15, 2020 at 10:08 am

    I’ve been to Boston a couple of times but haven’t seen a lot of the places you posted! I will be saving this for my next trip out there!

    • Taylor Deer on November 15, 2020 at 11:15 am

      It’s such a beautiful city! The things to do there are endless. 🙂

  13. Emma on November 15, 2020 at 12:47 pm

    Boston is such a great city. I really want to go back again soon. Last time I was there was with my friend and it was an amazing girls trip. We did some of the touristy stuff but also just enjoyed checking out the city. I need to visit some of those breweries though. Next time for sure

    • Taylor Deer on November 15, 2020 at 8:23 pm

      Boston really is amazing! I feel like you definitely have to do the touristy stuff there. Also the food is great too! 🙂

  14. Ildiko on November 15, 2020 at 7:53 pm

    What a fun blog! I do love Boston. Learned so much. I would love to stay at the old jail cell Hotel. Very cool concept. I also love history so would enjoy the Paul Revere House and Boston Harbor. Great foo recommendations too!

    • Taylor Deer on November 15, 2020 at 8:24 pm

      Thank you Ildiko! It sure was a lot of fun staying at the Liberty Hotel. 🙂

  15. Vanessa Shields on November 15, 2020 at 8:03 pm

    I love Boston! Such a fun city with so much history and is a great weekend getaway ant time of the year. The Liberty Hotel is such a great place to stay for its unique history and fun decor!

    • Taylor Deer on November 15, 2020 at 8:24 pm

      It really is a great city! The Liberty Hotel really is a lot of fun! 🙂

  16. Courtney on December 7, 2020 at 6:03 pm

    I LOVED this post! I’m dying to explore Boston and your article listed so many incredible places! Such a fun read.

    • Taylor Deer on December 7, 2020 at 6:23 pm

      Thank you Courtney! You totally have to go to Boston at some point. It is a beautiful city. 🙂

Leave a Comment





23755562_10155876287232640_5245508374282114067_n

Fall foliage in Boston

Boston, Massachusetts is a beautiful city that cannot be missed when visiting the East Coast of the United States. In fact, Boston makes for the perfect girls weekend getaway and I cannot wait to show you why!

The city of Boston is the capital of Massachusetts and it was named after a town in England. It’s one of the most popular and abundant cities in the USA and the city was also home to the Boston Tea Party in the late 1700s. Nowadays, this quaint U.S. city is located in New England and is filled with charming neighborhoods, amazing restaurants, fun bars, beautiful parks and a lot of history. It’s the perfect place to visit in the fall!

Stroll through Beacon Hill during a girls weekend in Boston

During fall 2017, my cousin and I visited New England for a well-needed girls weekend in Boston and we ended up having the time of our lives! (I also revisited Boston with a friend during autumn 2020.) Overall, Boston makes for one of the best fall vacations on the east coast!

In addition, visiting New England during autumn is a beautiful site to see since the colors of fall foliage are in full swing. When planning a fall getaway, you cannot do wrong with anywhere in New England. If you’re looking for a fall weekend trip from Boston, visiting destinations like Salem, the White Mountains of New Hampshire, Woodstock, Vermont and the Berkshires will not leave you disappointed.

In this article, discover the best things to do during a girls weekend getaway in Boston.

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like.


Pin the Below Image to Keep Handy

A Weekend in Boston

Planning a Trip to Boston:

Beacon Hill during a girls weekend in Boston

Since Boston is a larger city, you can easily travel there from anywhere in the world by taking a flight into Boston Logan International Airport. You can find affordable flights through Skyscanner!

Other ways to get to Boston are through public transportation. The Amtrak train runs from major U.S. cities like New York, Philadelphia and Washington D.C. and takes passengers to Boston every day! If you’re coming from the New York City area, like I did, you can either drive to Boston or take a Flixbus.

From the New York area, it is around a 3.5-hour drive to get to Boston, depending on traffic. From Philadelphia, it takes 5 hours to get to this stunning city and from Washington D.C., it takes over 7 hours to get to “Beantown”. If you decide to drive to Boston and either don’t want to put miles on your vehicle or even if you do not have a car of your own, it is best to rent one.

For those who fly into Boston, the best way to get from the airport to your accommodation is via a taxi or ride sharing app like Uber or Lyft. Another way to get to your hotel is through Go Airport Shuttle!

Looking for an RV for your next trip, reserve here!

Where to Stay in Boston for a Girls Weekend:

A woman at the Liberty Hotel in Boston

Thanks to Crawford Concierge, the hotel that my cousin and I stayed at during fall 2017 was EPIC! They helped us plan the perfect girlfriends guide to Boston!

The Liberty Hotel is located in Beacon Hill, which is 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.

From 1851 through 1973, the jail 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 in 1990, the last prisoners were moved to the new Suffolk County Jail. In the early 2000s, the old jail was remodeled into a beautiful, luxury and innovative hotel. Apart from renovating the building, the jail’s granite exterior and expansive interiors remained unchanged.

The jail cells were wrought-iron gates that were featured within the hotel lobby, restaurant and bar. They are examples of preservation! It was cool staying in an old jail during this fun girls weekend in Boston! Plus, the place was rocking with people having a good time.

In addition to The Liberty Hotel, you could find numerous hotels to suit your budget in Boston. There is also a variety of rental options that make for great places to stay in Boston!

Best Places to Stay in Boston:

Luxury: Fairmont Copley Plaza (I stayed here my second time in Boston in 2020.)

Boutique: Kimpton Nine Zero Boston

Mid-Budget: Boston Marriott Long Wharf

Budget: HI Boston Hostel

Food and Entertainment in The Liberty Hotel:

Staying at the Liberty Hotels during a girls weekend in Boston

Liberty Bar: Before my cousin and I enjoyed our first night “out” in the hotel, we savored an amazing burrata, truffle and arugula pizza at Liberty Bar. (It was amazing!)

This bar is a great place to casually grab food and drinks in the hotel. It is also the perfect spot for an afterwork drink! I say it like that because happy hour bars are actually illegal in the city of Boston.

A mug shot of Lindsay Lohan at the Liberty Hotel

Alibi: For some late night dancing and fun, my cousin and I went to 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. We had such a blast dancing and meeting new friends at Alibi.

Staying at the Liberty Hotel in Boston during a girls weekend

Clink: During a girls weekend in Boston, it is obligatory to get brunch! Since The Liberty Hotel had so many great places to eat, 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.

During my first trip to Boston in 2017, I enjoyed one of the best brioche French toast dishes with Canadian maple syrup and Vermont maple sausage on the side. My cousin had the smoked chicken quesadilla. (I had an omelet during my second Boston girls weekend in 2020.)

Brunch during a girls weekend in Boston

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! My cousin took advantage of it while I had a mimosa.

In addition to the above, The Liberty Hotel also has another fine dining Italian restaurant called Scampo, an outdoor venue called The Yard, an upscale bar called Catwalk and they also have great room service.

Where to Eat and Drink during a 3-Day Boston Itinerary:

Two women enjoying at drink at a speakeasy during a girls trip in Boston

Pauli’s: Since we were in New England, it was only right that my cousin and I get a lobster roll during our weekend Boston trip in 2017.

Prior to going to Boston, I was recommended a delicious lobster roll joint in the North End area called Pauli’s. You can choose between a hot and buttery lobster roll (Connecticut roll) or a cold mayo roll (Maine roll). I got the Connecticut roll and my cousin got the Maine roll.

In addition to lobster, you can also get Italian sandwiches, salads, burgers, wraps and more! Pauli’s is a great place, but it gets crowded and there isn’t much seating room.

Dolce Vita Ristorante: During our girls weekend trip in Boston, 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 cafés to enjoy a delicious meal or treat. We were recommended to check out Dolce Vita Ristorante on Hanover Street.

The owner, Franco Graceffa, was friendly and welcoming as we stepped into his restaurant. The restaurant itself is spacious with a lot of seating and there is even a wine bar if you wish to enjoy antipasti or light appetizers.

For my main meal, I savored fettuccine with jumbo shrimp and scallops in a white wine tomato sauce with fresh sun dried tomatoes. Alexie had a delicious gnocchi dish in a vodka sauce.

An Italian dinner from La Dolce Vita in Boston

Drink: Located in the Fort Point area of Boston is a speakeasy bar called Drink that blends classic cocktails of the prohibition era with modern artisanal ingredients. It is one of the best spots to have fun in Boston this weekend and beyond!

Drink is a hotspot in Boston, so there was a line to get into the bar area (when I visited in 2017). At the time, we only had to wait 15 minutes and once we got in, I fell in love with the atmosphere.

Overall, 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 what flavors you like in a cocktail. In 2017, I liked my cocktails more sweet and not strong, I told our bartender that I enjoy anything maple syrup-related, molasses and rum. In addition, Alexie loves spices, so he made the perfect drink for both of us. I couldn’t recommend this place more! (Next time, I’d love to try their smokey cocktails.)

State Street Provisions: During my second girls weekend trip to Boston in 2020, my friend and I enjoyed a lovely dinner at the rustic and contemporary restaurant of State Street Provisions in the Long Wharf area.

I loved the ambiance at State Street Provisions and during our evening, I savored a delicious Angry Queen Pizza (which was a Margherita pie) with a fall sangria. My friend had the steak frites with a sangria too. Everything was amazing!

Pizza from State Street Provisions in Boston

Mike’s Pastry: Located in Boston’s North End along with Cambridge, Somerville and TD Garden, Mike’s Pastry was founded in 1946 and it’s known as one of the best Italian pastry shops in the city.

Owner Michael Mercogliano created a one-of-a-kind cannoli that keeps locals and tourists coming back for more. It is at this amazing pastry shop where you could get cannoli and pastries, Italian cookies, pies, cakes and gelato. It is a MUST if you are visiting Boston!

I unfortunately didn’t make it to Mike’s Pastry with my cousin in 2017, but my friend and I visited the Cambridge location in 2020. I got the Nutella cannoli, which was amazing and my friend got the lobster tail, which she also enjoyed!

The Best Itinerary for a Girls Weekend in Boston:

Wander through Beacon Hill:

A woman sitting on a stoop in Beacon Hill during a girls weekend getaway in Boston

A girls weekend in Boston would not be complete without getting lost in Beacon Hill, the city’s most charming area.

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.

Discover 5 misconceptions and 5 truths about life in Boston!

A beautiful building in Beacon Hill of Boston

I mainly got to explore Beacon Hill during my getaway in 2017 because I had more time, but I also had the opportunity to walk through a piece of it during my shorter time in Boston in fall 2020. It’s one of the best places to explore during your girls weekend in Massachusetts!

Overall, my cousin and I were lucky when we visited in 2017 because the weather wasn’t as cold as we expected it to be, but we still kept extra warm by visiting the cute coffee shops in Beacon Hill.

Rouvalis Flowers in Boston, Massachusetts

As we continued to wander around Beacon Hill, we stopped at another gem called Rouvalis Flowers. This lovely corner shop offers a warm and welcoming feeling right from the moment 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.

Walk through Boston Public Garden and Boston Common:

A woman strolling through Boston Public Garden

Two great places to walk around in the city during fall trips in Boston are the Boston Public Garden and the Boston Common.

The Boston Common is a 50-acre urban park that hosted the British troops during the American Revolution.

The Boston Public Garden, on the other hand, has different walking paths, beautiful Spanish moss trees, adorable animals and a lovely bridge that goes over a little pond. They are both romantic places in Boston to stroll around and admire beautiful nature.

Make a Visit to the Cheers Bar:

The Cheers Bar in Boston, Massachusetts during a girls weekend

Right across the street from the Public Garden is the iconic Cheers Bar from the Nick At Nite sitcom, Cheers!

I used to always watch Cheers at night when I was in elementary school, so of course the bar was on my bucket list and I thought it was funny that we just stumbled upon it unexpectantly rather than searching the entire city for it.

The Cheers Bar is actually bigger than what you could imagine! It’s a fun experience to add to your Boston itinerary.

A woman enjoying a beer during a Boston girls weekend

There are three rooms at the Cheers Bar: 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!

Visit the Paul Revere House:

If you are big history person, then you will totally love Boston! There are so many memorable and crazy things to do in Boston to learn all about the city’s past.

Since my cousin and I were only in Boston for a short, girls weekend, we didn’t have the time to see all of the historical sites. One place you must see is the Paul Revere House. Built in 1680, this colonial building was home to the American patriot Paul Revere during the Revolution.

Shop Your Way through Newbury Street:

Go shopping on Newbury Street during fall in Boston

If you are a big shopper, then you definitely have to head to Newbury Street during a girls trip, which is located in the Back Bay area of Boston.

It is on Newbury Street where you could find fashion stores, consignment shops, restaurants, coffee shops, hotels, beauty salons, bars, art galleries, tourism offices and so much more!

Stroll around Boston Harbor:

Enjoy the Boston Harbor during a girls weekend in Boston

Known as the site of the Boston Tea Party, Boston Harbor is a peaceful place to stroll around and admire the beauty of the city.

The Boston Tea Party took place on December 16, 1773 when members of the Sons of Liberty dumped crates of tea into the Boston Harbor as a way to protest against the Tea Act and its provisions for taxation of tea. Nowadays, it is home to the Port of Boston, which is a major shipping facility in the Northeast.

Overall, Boston Harbor is a beautiful area to walk around, admire a sunset and relax at. It’s one of the best vacation spots in Boston, Massachusetts!

Attend a Sporting Event during your 2 Days in Boston Itinerary:

Seeing a New England Patriot's game during a girls weekend in Boston

Whether you’re visiting Boston in fall, when the New England Patriots are playing, or in the spring, when the Boston Red Sox play, I highly recommend attending a sporting event because the spirit in the city is unreal.

Fenway Park (where the Red Sox play) is a great place to visit year round since concerts are also held there.

Enjoy an Afternoon at a Boston Brewery:

A woman drinking a beer at Harpoon Brewery in Boston during a girls weekend

Samuel Adams Brewery: Known as Boston’s most famous lager, Samuel Adams is a must-visit when you’re in the city during a girls weekend.

Please note though that the brewery is closed on Sundays. Unfortunately, my cousin and I didn’t get a chance to go in 2017 since we didn’t know that originally.

Each year, beer enthusiasts at Sam Adams travel to Germany to select the world’s best heirloom aroma hops for their lager!

Harpoon Brewery: Since Sam Adams was closed, my cousin and I made our way to Harpoon Brewery, located in South Boston on the Boston Main Channel. Spending a day at this spot makes for one of the best girls weekend activities!

Harpoon Brewery is a lively and fun bier hall that features renowned beers straight from the source along with German and American food.

We both 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.

A craft beer flight from Cambridge Brewing during a girls weekend in Boston

Cambridge Brewing Co.: During my trip to Boston in 2020, my friend and I decided to check out the Cambridge area (including Harvard University) and had lunch at Cambridge Brewing Co.

Located in Kendall Square, Cambridge Brewing Co. is the oldest brewpub in the Greater Boston area and it offers flavor-forward beers using only water, malt, hops and yeast.

My friend and I had lunch at this great spot and enjoyed a flight of four delicious beers. I had the Cambridge Amber, which is an American Amber; The Great Pumpkin Ale, which is made with local pumpkins; I Remember My First Check-in, which is a kettle sour gruit and Heather Ale, which is an unhopped herbal ale.

For lunch, I savored the delicious fried chicken sandwich with fries and my friend had the buffalo chicken tenders that also came with fries. Everything was delicious!


Other trips you must take with your girlfriends:

7-Day New England Fall Road Trip Itinerary

A Perfect Girl’s Getaway at Woolverton Inn

Best Girl Trip Destinations in the World

I hope you all enjoyed reading about the best things to do during a girls weekend in Boston, Massachusetts. If you have any questions about my time in Boston, please email me at info@browneyedflowerchild.com.

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., MA State Capital: Boston, Time Zone: Eastern Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my Boston look:

Click here to shop my Poshmark closet!

32 Comments

  1. Merrie Rodriguez on August 19, 2019 at 8:11 am

    My husband and I have really been wanting to head to Boston for the longest time! Hopefully we can get there soon!

    • Taylor Deer on August 19, 2019 at 12:03 pm

      It’s a great city and I highly recommend it for the fall! 🙂

  2. Courtney Delfino on August 19, 2019 at 2:34 pm

    My favorite part of Boston is for sure Boston Common! Such a beautiful park! Great read Taylor!

    • Taylor Deer on August 19, 2019 at 3:56 pm

      Yes, I loved the Spanish moss they had. It was so lovely!

  3. Josefine on August 19, 2019 at 3:28 pm

    I’ve been wanting to go to Boston for the longest time! I’d love to see the leaves during fall some time ? it looks like you had a great time there! And the photo of Boston from above is crazy beautiful!!

    • Taylor Deer on August 19, 2019 at 3:57 pm

      You definitely have to make your way to the Northeast of the United States during the fall season. It is so beautiful and you would love it! 🙂

  4. Zsuzsanna Paluska on August 20, 2019 at 9:52 am

    Such a nice trio, loved to read your experiences! Boston sounds like a perfect city for a weekend getaway! It’s our dream to visit the US one day, we can include Boston in our itinerary ?

    • Taylor Deer on August 20, 2019 at 12:24 pm

      Thank you so much Zsuzsanna! I highly recommend to visit Boston during the fall season. It is so beautiful! 🙂

  5. World of Lina on August 22, 2019 at 5:12 am

    I don’t know why but I have the feeling I would totally love Boston! Looking at your photos makes me wanna book a flight there immediately ☺️

    • Taylor Deer on August 22, 2019 at 8:49 am

      Yes, I loved it so much when I went almost two years ago. My cousin and I had such a blast and I totally recommend going in the fall! 🙂

  6. Bucketlist Bri on August 22, 2019 at 4:42 pm

    Aww another beautiful blog post, Tay! Ya know I just went through Portland, Maine the other day and thought of you. Shame we didn’t make it to Boston!

    • Taylor Deer on August 24, 2019 at 4:45 am

      Thank you so much Bri! Ah I hope you enjoyed Portland. Next time you have to make it to Boston! 🙂

  7. Francesca on November 2, 2020 at 12:08 pm

    I love Boston! It would be such a fun place for a girls weekend! The Samuel Adams Brewery was so fun. I also love wandering around the Boston Common and Public Gardens.

    • Taylor Deer on November 2, 2020 at 11:20 pm

      It really is a beautiful city! This recent trip was my second time in Boston and I fell in love with it even more! 🙂

  8. Katiesaway on November 4, 2020 at 8:34 am

    I love it in Boston! My uncle moved there a few years ago so we have been to visit a few times! Such a beautiful and calm city

    • Taylor Deer on November 4, 2020 at 9:41 am

      It really is a stunning city! I want to go back and see more. 🙂

  9. Megan on November 14, 2020 at 12:26 pm

    oh my goodness that is SO cool you could see the Cheers bar! What a cool stop!

    • Taylor Deer on November 14, 2020 at 5:45 pm

      Yes, it was a fun place! Much bigger than I would’ve imagined though. 🙂

  10. Jamie on November 14, 2020 at 4:30 pm

    Boston has so many great breweries, and the Public Gardens are my favorite!

    • Taylor Deer on November 14, 2020 at 5:47 pm

      Yes, I loved them all, especially Cambridge! 🙂

  11. Krista on November 14, 2020 at 6:07 pm

    These are some great places to visit in Boston for a weekend away! Adding some of these stops to my list for when I visit the city.

    • Taylor Deer on November 15, 2020 at 9:58 am

      Yes, I love Boston so much! It is such a beautiful city! 🙂

  12. Rebecca on November 15, 2020 at 10:08 am

    I’ve been to Boston a couple of times but haven’t seen a lot of the places you posted! I will be saving this for my next trip out there!

    • Taylor Deer on November 15, 2020 at 11:15 am

      It’s such a beautiful city! The things to do there are endless. 🙂

  13. Emma on November 15, 2020 at 12:47 pm

    Boston is such a great city. I really want to go back again soon. Last time I was there was with my friend and it was an amazing girls trip. We did some of the touristy stuff but also just enjoyed checking out the city. I need to visit some of those breweries though. Next time for sure

    • Taylor Deer on November 15, 2020 at 8:23 pm

      Boston really is amazing! I feel like you definitely have to do the touristy stuff there. Also the food is great too! 🙂

  14. Ildiko on November 15, 2020 at 7:53 pm

    What a fun blog! I do love Boston. Learned so much. I would love to stay at the old jail cell Hotel. Very cool concept. I also love history so would enjoy the Paul Revere House and Boston Harbor. Great foo recommendations too!

    • Taylor Deer on November 15, 2020 at 8:24 pm

      Thank you Ildiko! It sure was a lot of fun staying at the Liberty Hotel. 🙂

  15. Vanessa Shields on November 15, 2020 at 8:03 pm

    I love Boston! Such a fun city with so much history and is a great weekend getaway ant time of the year. The Liberty Hotel is such a great place to stay for its unique history and fun decor!

    • Taylor Deer on November 15, 2020 at 8:24 pm

      It really is a great city! The Liberty Hotel really is a lot of fun! 🙂

  16. Courtney on December 7, 2020 at 6:03 pm

    I LOVED this post! I’m dying to explore Boston and your article listed so many incredible places! Such a fun read.

    • Taylor Deer on December 7, 2020 at 6:23 pm

      Thank you Courtney! You totally have to go to Boston at some point. It is a beautiful city. 🙂

Leave a Comment





Related posts

What to Eat at German Christmas Markets

A trip to Germany in December is not complete without visiting the Christmas markets (or Christkindlmarkts) that pop up in...
check out the post

A Day Trip to Hallstatt from Salzburg

Known as one of the most photographed destinations in the world, Hallstatt, Austria is a magical place to visit during...
check out the post

Warm Places to Visit in November

November is one of the best times to enjoy a great trip before the start of the holiday season. From...
check out the post