Sober Travel Guide: Boston
… rich in history, culture, and undeniable charm
Boston, Massachusetts, baby. Isn’t that fun to say?
Founded in 1630, Boston is one of America’s oldest cities. While Boston is known for its cobblestone streets and historic landmarks, make no mistake that Boston is more than just what it used to be.
Exploring Boston was a true delight. Highlights include hopping on the famous Swan Boats in the Public Garden, feeling like a true sports fan at Fenway, and catching an epic concert at one of the city’s most iconic venues.
It doesn’t hurt that Boston’s Mayor is a woman named Michelle. ;) Under her leadership, Boston is more welcoming and is an amazing city to explore sober.
I loved the historic beauty of Beacon Hill and the Italian vibes in the Northend, and felt that Boston offered endless ways to connect to its culture, scenery, and community - all without a drop of booze.
Whether you’re visiting for the history, sports, or arts, the guide is meant to experience the best of Boston, completely sober and fully present.
Let’s dive into all the amazing things that Boston has to offer.
But first, does anyone remember this song by Augustana? It was released in 2005 and has been stuck in my head since I visited..
Getting to Boston:
For domestic flights, I love Southwest. I’ve been flying with them for years and love the vibe. I always chuckle when the flight attendant makes a joke before or after landing.
If you’re considering flying with Southwest (or any airline, honestly), I recommend signing up for their Southwest Rapid Rewards® Credit Card.
I’ve had great experience using points for flights & I’m always impressed with their customer service.
Getting around Boston:
According to walkscore.com, Boston has been dubbed “The Walking City” and is a perfect place for a pedestrian. Also home to MBTA, Massachusetts Bay Transit Authority, America’s first subway system, Boston is the 3rd most walkable large city in the US with 617,594 residents.
Getting around Boston is easy. After taking a shuttle from the airport to the Silver Line, I purchased a “CharlieCard.” This card cost about $20 and was good for an entire week. The card can also be used for buses and ferries in the Greater Boston metro.
Tbh, I was getting European vibes while using public transportation, and I’m optimistic that more cities in the States will prioritize this.
Another great option is the Blue Bike Adventure Pass, which is citywide. A $10 pass gives you 24-hour access to literally thousands of bikes in Boston for unlimited 2-hour rides. This was a blast! I love riding bikes in new cities to explore, and there are plenty of bike lanes downtown.
Usually when traveling in the US, I like to get rental cars, just so it’s super easy to get around, but after Boston I’m feeling inspired to utilize more city public transportation - it’s a cool way to see more the city which is important to me.
You definitely don’t need to rent a …….
Staying in Boston:
I stayed at The Liberty, a Marriott property in Beacon Hill. It’s a cool mix of history and luxury, set in what was once the Charles Street Jail.
The hotel keeps a lot of the original 19th-century architecture, so you get this unique vibe where old meets new. You can still see the cell bars and catwalks, which was rad.
Other luxury hotels I recommend in Boston (in no particular order):
The Langham Boston
Mandarin Oriental Boston
Four Seasons Hotel Boston
To make your trip to Boston even more epic, book your hotel using this link. You’ll receive VIP amenities, upgrades, and other exclusive offers.
Cute Neighborhoods Everywhere
When it came to exploring Boston’s neighborhoods, I spent the most time wandering through Beacon Hill's historic charm, soaking up the sports vibes in Fenway, smelling delicious pasta in the North End, and eating dumplings in Chinatown.
Each neighborhood has its unique personality and something special to offer, and I wish I could have spent time in every single one! If you’re planning to visit Boston, you can look at all of the Boston neighborhoods below to see which one you’d love to enjoy.
1 NA Bottleshop & 3 Mocktails to try in Boston
Dray Drinks: Boston’s NA Bottle Shop
The rise of non-alcoholic bottle shops is a promising trend, and Boston is now part of it with the opening of Dray Drinks in the South End in 2023.
Dray Drinks is the city’s first store dedicated entirely to non-alcoholic beverages. The NA bottle shop offers a wide range of products, from zero-proof liquors, beers, and wines to canned mocktails. Founded by Pat Dooling, who was inspired by a growing demand for alcohol-free options during the pandemic, the shop is helping to shift Boston’s traditionally alcohol-focused culture.
Dray Drinks carries over 200 thoughtfully selected products, including non-alcoholic wines made through traditional methods with the alcohol removed and even unique creations like CBD-infused seltzers. What I love about the store is that they aim to build a community around zero-proof living, hosting events, and donating a portion of profits to local addiction and recovery causes.
Follow them on IG @draydrinks
Mocktail #1: Every Free Spirited Beverage at Comfort Kitchen
While this woman-owned cafe by day and restaurant by night is technically outside Boston, their menu is outta this world. Comfort Kitchen’s take on mocktails is this:
Around here, we don’t call them “mocktails.” We prefer to be free-spirited!
I’m obsessed, and I’ll let the menu speak for itself:
Follow them on IG here: @comfortkitchenbos
Mocktail #2: Winter Melon Smash at Wusong Tiki Bar
Located in Harvard Square, this tiki bar combines a playful & retro atmosphere with a creative drink menu that features both classic and modern tiki cocktails/mocktails.
I know this is meant for mocktails, but can we just take a second to look at their bao buns?!
Like WHAT?!?!
Their menu offers a range of unique, flavorful drinks, including their imaginative mocktails. A must for your next trip to Boston.
Follow them on IG @wusongroad
Mocktail #3: Self Care at Café Sauvage Boston
This hip Parisian bistro opened in 2021, and never looked back. Owned by a wife & husband (so freaking cute), both originally from France after having worked at various French restaurants in the city. Their food menu is WOW and blends traditional French cuisine with influences from Vietnam, Portugal, Ethiopia, and more.
The Zero Proof selection showcases their attention to detail - I mean, coconut lime foam?! Yes, please.
Follow the French cafe on IG @cafesauvageboston
For those who are always down to try something new:
Lifebloom Candles:
I love this couple and what they’re doing. This candle-making bar allows visit to craft their own custom-scented candles, choosing from so many different smells and colors to create a one-of-a-kind product. It’s a perfect activity for friends, lovers, family, and even solo. They guide you through the entire hands-on process, letting your creativity spark a flame. See what I did there?
They have two locations, one Boston Public Market and another storefront in South Boston.
Now, this is a bar I can get behind.
Follow them on IG @lifebloom.
Afrobeats Dance Boston
If you love to dance and experience other cultures, don't miss Afrobeats Dance every Wednesday at 6 pm in Roxbury where you can join the free dance workouts hosted by the Afrobeats Dance Boston dance company.
These sessions, created in partnership with the Boston Parks and Recreation Department as part of their Winter Fitness Series, are set to energetic African Pop music and celebrate dance and movement styles from Nigeria, Ghana, and more. AMAZING. And if you can't make it to the free Wednesday classes at the Vine Street Community Center, the studio also offers regular community classes starting at just $15.
Follow them on IG @afrodancebeatsboston_ and follow their upcoming events here.
FENWAY PAHK
Fenway Park is a must-visit for any trip to Boston, and I had a blast catching a Red Sox game against the Diamondbacks. The energy in the stadium was AWESOME, especially when I saw someone hit the ball right to Pesky's Pole for an automatic home run—iconic.
While the mocktail options were limited, I kept it simple with just water and a classic Fenway hot dog. The atmosphere was so fun, with everyone cheering and enjoying the game, making it an unforgettable experience in Boston and something I’ll remember forever.
Iconic Landmarks
Charles Street
My hotel was a block away from Charles Street and on the way to Boston Public Garden, so I spent a lot of time walking up and down the iconic street.
Charles Street in Beacon Hill offers a charming mix of unique boutiques, art galleries, book shops, and a palm reader. You can find everything from women's fashion and gifts to vintage and preppy clothing, antiques, art, stationery, and pet supplies.
There are plenty of cozy cafes and restaurants to explore, too.
Boston Public Garden
The Boston Public Garden, established in 1837, was America's first public botanical garden. It makes sense, but isn’t that SO COOL?!
The garden is maintained by the Boston Parks Department and supported by a non-profit with over 2,000 members dedicated to maintaining all of its 24 acres.
In my sobriety, I have grown to love visiting parks, and while I travel, I spend time in nature with the beautiful landscapes. It’s easy to feel overstimulated while traveling, and I’ve found that a couple of hours in the park can do wonders for the heart and soul.
Swan Boats
The Swan Boats!! This might have been my favorite thing.
The Swan Boat story dates back to the 1870s when Robert Paget, whose family continues to operate the business, was granted a boat for hire licensed by the City of Boston. Rowing a small boat in the Boston Public Garden lagoon was a favorite summer pastime for city residents at all hours of the day. ADORABLE.
The Paget family has kept up this tradition for almost 150 years, maintaining the charm and integrity of a vision that became a reality for a young boat builder and his wife. They are the only boats of their type in the world and are an iconic symbol of Boston. SO EPIC!
This cost $9 for two adults, and it was so worth it.
Boston Common
Boston Common, established in 1634, is America's oldest public park and a historic centerpiece of the city.
It was used as a communal ground and a site for public gatherings (I witnessed a few while visiting), and it has evolved into a beloved green space. The Common has beautiful lawns and shaded pathways and is right across the street from Boston Public Graden.
Boston Tea Party
I’m no history buff, but it’s cool to know what happened where you’re visiting.
In 1773, a group of radical Bostonians dumped A LOT of tea into the Boston Harbor to protest what they believed were “unjust” taxes imposed by the British Parliament, aka the “Boston Tea Party.”
As I learned more, it became clear this was quite controversial. Benjamin Franklin and George Washington disapproved, and it took nearly 100 years for it to evolve from being viewed as a reckless act to becoming a celebrated part of American history.
Boston does a great job of showcasing the historical impact of this event and even has a dedicated space to enjoy tea where the event happened: Abigail’s Tea Room & Terrace, known as the best place for afternoon tea.
If history is your thing, check out this Boston Tea Party Guided Museum Tour.
USS Constitution
The USS Constitution is a treasured piece of American history anchored in Boston Harbor at the Charlestown Navy Yard. Launched in 1797, it’s still the world’s oldest warship.
Today, the USS Constitution is a living museum where visitors can step aboard and get a feel for life at sea in the 18th century. You can explore the decks, see the cannons up close, and hear fascinating stories from active-duty sailors dressed in period uniforms. A super fun spot if you’re into history!
The Hahvahd Touah
One of the highlights of this sober Boston adventure was the student-led tour of Harvard, where we got to dive into the iconic university's rich history and traditions. Our guide, an adorable, sweet gal named Quee, had just graduated from Harvard with a DEGREE IN PHYSICS. FROM HARVARD.
….
She was gearing up to start her master’s in the same field. I wondered if I was smart enough even to be standing next to her…
…..
Anyway, she was AMAZING! She brought the campus to life with her stories and insider knowledge, making the tour super informative and interesting, which was unexpected. I only had one question - where did Zuck create Facebook?
Quee showed us the dorm where Facebook was created and later took us to one of the many libraries where we spent a lot of time learning about the backstory of the library’s namesake.
The Harry Elkins Widener Memorial Library is Harvard’s flagship library, with its massive collection of around 3.5 million books. Sounds like heaven on earth.
It was named in honor of Harry Elkins Widener, a 1907 Harvard grad and avid book collector. The library was a tribute built by his mom, Eleanor Elkins Widener, following his tragic death on the Titanic in 1912. With family wealth, Harry and his father, George Dunton Widener, had access to the lifeboats on the ship and heroically gave up both of their spots to women and children on the ship. Eleanor survived and passed on their beautiful legacy through this library.
Seafood
Two words: Alive & Kicking. Or is that 3?
This seafood spot DOESN’T EVEN HAVE A WEBSITE. That’s how you know it’s good.
This no-frills spot is known for its lobster sandwich, and omg, whoever said there is no God has never tried this sandwich. IT’S CHUNKS OF LOBSTER ON HOMEMADE BREAD.
It paired perfectly with their lobster bisque and honestly if I ever get married I’ll just do it here.
Another quintessential spot in Boston is The Barking Crab. This place has a website, and it also has a wait.
I waited extra long for a table on the water, I’m all about those views.
If I had just eaten a lobster sandwich and lobster bisque, I would have ordered one of their infamous 3lb lobster meals. ($88) This time I went for oysters.
I was too busy eating horseradish to order mocktails, but you can see their Zero Proof options in their drink menu below.
If you’re like me and obsessed with seafood, check out this Small Group Boston Seafood Lovers Tour. Thank me later.
Chinatown
Chinatown in Boston is just a short walk from the Boston Public Garden, Charles Street, and Boston Common, making it a perfect stop while exploring.
The neighborhood has a great vibe, filled with different options for delicious food. I couldn’t resist trying the amazing dumplings—fresh, flavorful, and exactly what I needed after a day of sightseeing.
I also quickly stopped into a local grocery to scope out the different options - so much seafood - and I was surprised to see eel as an option. Can we eat eel?!
I almost tried the Roasted Garlic Oyster flavor chips but chickened out at the last second.
Emo is for lovers
I love live music, and another highlight of my visit to Boston was seeing New Found Glory on the 20th anniversary of their album Catalyst. The venue? Roadrunner. So epic. It’s a gem with a super intimate vibe, yet big at the same time. Not sure how they do that. The energy was amazing, and I felt right at home. While I wasn’t a huge New Found Glory fan, I am now. The venue didn’t have many NA options, so I opted for my go-to: water.
Their concert was full of crowdsourcing, people screaming at the top of their lungs, and even a Disney cover by the band. They ended with a confetti cannon.
It was a perfect introduction to the Boston music scene, and that experience inspired me to explore more concerts in other cities and be open to new bands and venues along the way.
Follow the venue on IG here.
Boston: until we meet again
While I knew Boston would be amazing, I was high-key blown away by all of it, and I have loved exploring new parts of our beautiful country.
The city truly offers a little bit of everything for the sober traveler - plenty of delicious seafood (you can’t enjoy that while hungover), visiting the halls of Harvard, or witnessing history at the legendary Fenway Park; there’s no shortage of iconic experiences here in Bean Town.
Boston vibes, history, and welcoming spirit make it a city I want to visit again - especially for that lobster sandwich.
If you’re ready to start planning your trip, use this link to look at all of the epic tours in Boston.
Next Steps for Sober Travel:
I hope this Sober Travel Guide to Boston gives you great ideas and helpful tips for your next alcohol-free trip.
I said it once and I’ll say it again: do not go to Boston without eating at Alive & Kicking.
Here are ways to travel better:
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Book exclusive travel experiences, including tours, excursions, and transfers here.
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Happy Sober Travels in Boston 💃
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