
Traveling Solo in Boston
Traveling solo in Boston, or anywhere for that matter, for the first time anywhere can feel intimidating. I had never had the opportunity to travel to a new city alone and I was eager to prove to myself that I could do it.
I found Boston incredibly walkable and tourist friendly. Between all the beautiful architecture, the historic landmarks, and the easy to use public transportation, it’s easy to get around Boston in just a few days.
What surprised me more was just how friendly all the people were. People usually hear the stereotype that Bostonians are blunt and speak their mind, but everyone I came into contact with offered up a wealth of knowledge and friendly conversation.
Practical information on Traveling Solo in Boston
Where to stay
Because I was working in Cambridge, I stayed right off the Lechmere stop just on the other side of the river. This made my commute to work just a 20-minute walk, but after hours, I could get into the city easily with the train. For those visiting just for funsies, I recommend staying downtown. You’ll be at the center of it all and be able to walk everywhere, no problem. If you don’t like walking, you can still take trains or bus lines, but I feel walking allows you to discover all the beautiful random quirky things in between main attractions.
How to get around
I recommend walking to allow for spontaneous discovery, but Boston does have a really great train system and buses that will take you anywhere. You can buy a “Charlie Card” at any bus station. This is how you will pay your train and bus fairs. If you need to get somewhere fast, there are pleanty of Uber and Lyfts.
The Weather
Much like a lot of cities back east, the summers are hot and humid and the winters are cold and snowy. Everything in between is often pleasant. I went for work in the height of summer and suffered under the humidity. I would recommend going in spring or fall if you don’t like dealing with extreme temperatures, but know that those are likely the height of tourist season as well.

Boston Common Park
139 Tremont St, Boston
Boston Common is alive with visitors and locals enjoying the good weather. Children squeal in glee, splashing each other, as they wade into the 1-foot pool. Ducks waddle by the edge of the pond at Boston Public Garden, unfazed by the tourists creeping closer and closer with their cameras. The willows dip their long limbs like tassels into the still waters, drawing intricate patterns and swirls. The humidity is heavy in the air, but does not detract from a perfect afternoon in the park.



As the park ends, the red brick buildings come into view.


Twentieth Century Ltd.
73 Charles St, Boston
It’s easy to overlook this small, basement level gem on Charles Street. You really have to be looking for it but if you spot the entrance, take the stairs down into the shop and enter a world of floor-to-ceiling displays packed with vintage jewelry, hats, and tiaras.
There is so much to look at and every piece has a story. If you ask the shop owner, he’ll likely tell you what he knows about it, with warmth and passion.
I quickly gravitated toward a display with a large crab pendant. It sat there dead-center, standing out against the silver and bronze bug pieces surrounding it. The shop manager began to tell me who made it and how it came to be in the shop. As he opened up more cases, I felt so welcome and really was touched by his willingness to talk to me and share his stories.
I left thanking him for the information and looked forward to coming back on a day when I could spend more time deciding on a vintage souvenir to take home. I recommend visiting Charles street and if you do, make sure you stop in and say hello at Twentieth Century Ltd.



Beacon Hill Chocolates
91 Charles St, Boston
From the street, you may confuse this with some sort of gift shop or stationery store. Vintage style art boxes in the window pique your curiosity. Upon entering, however, you are delighted to discover that this place not only sells the pretty boxes, but you can buy artful chocolates to go inside!



It took me nearly 5 minutes of staring at the display to decide on my 4 chocolates to take home.

I opted for the traditional vintage Boston box, though the mermaid one was a close contender.

My chocolate choices: Banana (yellow), Mint (leaves), Toffee (regular), and their famous Caramel Sushi Swirl

Quincy Market
206 S Market, Boston
Quincy Market and Faneuil hall seem to be interchangeable. A local told me they are right next to each other and often get confused for one another. This whole area is full of food, shopping, and street performers. Most locals will tell you it’s a tourist trap, but not being from here, I will say that it’s still fun to walk around. I recommend a short visit, get food amongst any one of the stalls, and take it outside on a nice day.



1630
4 S Market St, Boston
At the edge of South Market building in Quincy Market, the store 1630 stands out with gold script lettering on the windows. Inside you can find unusual Boston-centric “curiosities”. Unlike any other gift store in Boston, it marries old American history with a contemporary twist to create unique and memorable gifts. It’s difficult to pick out just one thing to buy. I ended up circling the room so many times that the store associate, a lovely lady named Anna, asked me if she could help me with anything. We got to talking and I learned that she actually makes the pins they sell at the counter. When she said that, I knew I had to have one. It doesn’t get any more personal and authentic Boston souvenir than that.


Everywhere you turn, there’s something new to admire.


Anna, The store associate, told me she reclaims old vintage books and recycles their pages by turning them into these pins. I picked one that had North America on it and she told me it came from an old astrology book. She then pulled out a bag behind the counter and offered me a free one-of-a-kind bottle opener shaped like a big pin. I chose one that I thought screamed my dad and knew it would be the perfect gift for his birthday. Check out her facebook page!

Marveling at Architecture and Landmarks
Downtown Boston is a hodgepodge of modern and old buildings. The city is littered with historic landmarks and from a map view, they all seem so easily identifiable. But when you’re actually in the middle of it all, you’re walking around and you might be standing right next to a historic building and miss it because you can’t back up enough to see what you’re looking at.



The old grain exchange building
As I was taking a photo of this building from right under that tree, a man came out of the building and approached me. He started telling me the building’s history and significance. He told me that it was made in 1891 and used to be the old grain exchange building. The went on to tell me all about how they remodeled the interior lobby and offered to take me up to the 7th floor to see some of the original interior. I would have loved to go, but being a solo female traveler, I was hyper aware that it would be better not to walk off with some stranger, no matter how nice he is. He was a lovely man and I could tell how much pride he had sharing that piece of history about this building. I could see it in his eyes and hear it in the friendliness in his voice. He disclosed to me that he had been managing this building for 30 years. He really made my day by taking the time to share his knowledge.


Old South Church, Backbay

Pin it!



Myfarrahdise
I feel envy, I wish can travel solo too when I have all the courage to do it, hahah! I love all your your photos, they are amazing Especially the black & white exchange building and church.
lorettamay
Thank you! You know I had the opportunity to go to Boston YEARS ago on my own for a conference, but I chickened out. It’s only recently after traveling with my husband so much that I’ve felt more comfortable getting around. I figure if i can navigate around in Norway where the signs aren’t even in english, i can probably do boston just fine. 🙂 Also I planned ahead by knowing exactly where to go for everything. Good luck to you!
Penny
I love the blue and white plate/decor. It is an integral part of Goa or rather the old Goa that we knew. I’ve seen it in Netherlands too. I think we got it from our Portuguese ancestory.
lorettamay
Wow Penny, that’s fascinating! I didn’t know that. Thanks for sharing!
Liz
I have never been to Boston but it looks beautiful. It kinda reminds me of London… Really beautiful pictures and great advice, thanks!
lorettamay
Thanks Liz! I’ve never been to London, but I want to go. We have a London office, so maybe I’ll be sent there in the future and travel solo there. Happy Travels to you!
Maxine
What an awesome idea, using old book pages to create pins. Beacon Hill Chocolates looks so pretty (and yummy). All your photos of your trip are very pretty 🙂
lorettamay
Thank you Maxine! I definitely plan on going back to Beacon Hill Chocolates. I was a little stingy and didn’t get any for my husband haha. They make great gifts!
Rajlakshmi
your photos are spectacular 😀 Thank you for this amazing virtual tour of Boston 😀
lorettamay
Thank you so much!
Missy
I had no idea there was so much beautiful architecture in Boston! It looks like you found great unique shops to look around in! Lovely photos, thank you for sharing!
Julie
I love Boston! I love all your beautiful photos of the city! I can’t wait to visit again!
lorettamay
Thanks, Julie! Yeah, I’m going back next month for work. Can’t wait to explore Harvard!
Christina
I am ready to book a flight from D.C. to Boston right now, just to get some of those Beacon chocolates!!!!! I have never been to Boston, but it is on my long list, especially since I just moved to the East coast. It is amazing to see so much culture and history there compared to other cities found in the U.S. Lovely post.
lorettamay
Thanks, Christina! There’s so much to see. I was only able to walk around a few hours for 2 days. I can’t wait to go back and see more.
Emma
Great post! It’s awesome to hear stories about other solo female travelers. Thanks for including a variety of different activities. Great info!
lorettamay
Thanks Emma! I’m Glad you liked it!
NieNie
I haven’t been to Boston since I was a kid and now I have been really wanting to go! I met someone on my travels who raved about Boston and these pictures definitely help sell me on the idea of traveling to Boston soon! Thanks!
lorettamay
It’s definitely worth a return visit as an adult! Thanks!
Zara
I would really love to go to Boston, especially in Autumn/Fall! You take lovely photos.
lorettamay
Thanks Zara
Victoria
I think you have truly captured the essence of Boston in this post. And your photos are amazingggg! I know how daunting it can be to go out somewhere for the 1st time. I’m glad you enjoyed yourself. If you ever go back make sure to check out Chinatown on a weekend. You won’t be disappointed
lorettamay
Thanks, Victoria!! I’m going back in two weeks for work again. Will definitely make it over that way!
Caroline
Boston has been on my list for awhile and it looks like a great spot to explore solo. Thanks for this guide, will save so I can check out some of these spots when I go!
Diana Petterson
Love your photos! I was just in Boston for the very first time and loved every minute of it. Thanks for sharing your story and photos!
lorettamay
Thanks Diana! Glad you liked it.
Steph
Gorgeous photos, they really give a sense of what it’s like walking around Boston. Wandering around new cities on my own is possibly my favourite thing to do in the world. And that chocolate place looks AMAZING!
lorettamay
Thanks Steph! I’m glad you like it.
Fritz & Susan
thanks so much for including our shoppe, 1630, in your post. we, too, like to think it’s “unlike any gift store in boston.” hope you had a great time visiting our city!
Tara Mouk
Where did you stay?
Did you walk to most of these places? Or use transportation?
lorettamay
Hi Tara,
I stayed just on the border of Cambridge and Boston at an Airbnb right off the Lechmere train line. I chose it because I was working during the week in Cambridge, but I wanted easy access to downtown Boston after work. The actual Airbnb wasn’t all that nice, so I didn’t mention it. I would recommend staying anywhere downtown. I particularly liked Charles street north of Boston Common park. I took the Lechmere from my Airbnb into town and then walked everywhere. Downtown Boston is very walkable.
Thanks for commenting!