Disclaimer: This Most Instagrammable Places In Boston post was originally written in August 2021 and was updated during spring 2022 for relevancy.
Happy August! This blog post is going to cover the most Instagrammable places in Boston! Boston has been my home for the past 23 years, although I’ve gotten to know the city especially well this past year. I’ve spent the past year exploring Boston more than ever before, and even became a tour guide through Airbnb, guiding people from around the world along the Freedom Trail on my History and Photo Tour! Unfortunately, I have to put these tours on pause for awhile because I’m moving to Charleston, SC for grad school, but hopefully I’ll pick them back up at some point. Boston is such a charming, historical city with so many hidden gems. I highly recommend walking around and exploring on foot. Hopefully this guide of the most Instagrammable places in Boston gives you some fun photo ideas for your visit!
Disclaimer: This blog post is sponsored by Staypinneapple Boston, a boutique hotel chain located in Boston’s South End neighborhood. I stayed here in July and created some content for them, and am working with them on this post! I highly recommend staying here next time you’re in Boston. As always, all opinions written below are my own.
1. Union Park
Located in Boston’s South End neighborhood, Union Park sits in one of the most charming streets in Boston. Here you’ll find rows and rows of brownstones, neighborhood parks, and even the occasional french bulldog!
2. Isabella Stewart Gardner Museum
This is my favorite museum in the world! Isabella Stewart Gardner was a modern-day girl boss, traveling the world solo and building up her own pristine art collection. After she passed, this museum opened in her honor and features her entire collection. The museum wraps around a center atrium that has been featured in several travel publications in the past. It’s definitely the most Instagrammable place in Boston!
Pro-tip: Watch “This Is A Robbery” on Netflix before visiting to learn about the art heist that happened here in 1990!
3. Acorn Street
Acorn Street is the official most photographed street in Boston. Trust me, I’m a tour guide… this is a fact! You can’t leave Boston without strolling through Beacon Hill and snapping a photo here.
Fun fact: Notice the divots near the curb on either side? These tracks aren’t from car tires, but wagon wheels! This road is over 200 years old and is one of the only original streets in Boston. I think it really adds to the charm of the neighborhood!
4. Fan Pier
Fan Pier is located in Boston’s newest neighborhood, the Seaport! This area is super fun to grab a drink in and offers a great view of the Boston harbor and skyline. Stroll along Fan Pier for this photo.
5. Cisco Brewers
Cisco sits along Seaport Blvd right in the Seaport District and is the perfect place to grab a drink. This beer garden also makes for a fun photo opportunity.
Pro-tip: There’s no happy hour deals in Boston, so don’t expect a discount at 5! You can expect a line though.
6. Tatte Bakery
This local chain definitely wins the award for the most Instagrammable place in Boston in terms of restaurants! The white interior + aesthetically pleasing lattes won’t disappoint if you’re a coffee lover.
7. Old State House
Even if the interior of the Old State House isn’t super Instagrammable, this shot definitely is! Stand on the corner of State Street and Congress Street to grab this shot. I always point it out to people on my tour!
8. Marshall Street Mural
Welcome to my favorite little street in Boston! This cobblestone road separates the Union Oyster House, the oldest restaurant in Boston, from Bell In Hand Tavern, the oldest bar in the US! Everyone on my tour says it reminds them of London, as it’s lined with old pubs and historical charm. There’s also a cute mural of Boston here! Marshall Street is definitely a top contender for the most Instagrammable place in Boston!
9. Ogawa Coffee
This coffee shop on Milk Street in downtown Boston is amazing year-round, but I definetly recommend adding this place to your fall New England bucket list! Ogawa is known for its seasonal latte designs!
10. Lookout Rooftop @ Envoy
Lookout Rooftop is Boston’s most popular rooftop and is a great place to visit for drinks or a special occasion. I recommend coming to this hotel at night to grab one of the best shots of Boston’s skyline!
11. Worcester Street
Another street in the South End that is probably tied with Beacon Hill for being the most Instagrammable place in Boston. Worcester Street is home to the most Instagrammable house in Boston (really, this is its official title). Want to visit? Plug 140 Worcester Street into your GPS. Remember to be respectful of locals while taking photos.
12. Rouvalis Flower Shop
Ok… I know I’ve said this about most places on this list, but THIS may actually be the most Instagrammable place in Boston. Rouvalis Flower Shop in Beacon Hill is the cutest little flower shop. They offer seasonal arrangements inside, and the exterior is just as precious. This area reminds me SO much of Europe!
13. Louisburg Square
Yet another Beacon Hill hot spot. Louisburg Square sits just behind Acorn Street, up a hill a bit. This square is home to some of the most photographed brownstones in Boston. Visit during the holidays to see some local decor and notice how stunning the ivy is here!
14. Brattle Book Shop
Welcome to one of America’s oldest and largest historical bookstores! This 3-story building is filled with used books and magazines, and even a few rare 1st editions. You’ve probably seen the outdoor section of this bookstore online before…be sure to snap a pic in the stacks adjacent to the building!
15. Boston Public Garden
Last but not least is Boston’s Public Garden, one of Boston’s well-known public parks! The Public Garden sits adjacent to the Boston Common, America’s first public park, although the Public Garden is probably more visited. There’s a beautiful man-made pond here with a picturesque bridge running over it. I recommend taking photos both on the bridge, with the skyline in the back, and near the pond so you can capture the bridge in the back. If you visit Boston in the warmer months, you can see the Swan Boats here too!
PS. Don’t forget the check out the sweet Make Way For Ducklings statue here!
And now for the sponsor of today’s blog post, Staypineapple! Staypineapple is a boutique, trendy hotel chain located in the US with locations in Boston, New York City, Chicago, San Francisco, San Diego, Portland, and Seattle. This hotel has one of the most playful, up-beat brands I’ve seen for a property and the most elegant rooms. I particularly enjoyed the Boston property because of the accommodating staff and ideal location. I showed up to this hotel 3 hours before my check-in time and they were able to store my bag for me, give me bottled water (it’s been a hot summer here in Boston), and provide the best restaurant recommendations. The location here is also great as the hotel sits adjacent to the South End and Back Bay neighborhoods in Boston. This area is less touristy than the Faneuil Hall area, for example, but is still within walking distance of popular sites like Newbury Street, the Prudential and Copley Malls, and the Boston Common. If you plan on visiting Boston soon, be sure to consider Staypineapple!
That’s all for today’s Boston post! This post covered the most Instagrammable places in Boston, but if you’re interested in learning more about what to do in Boston, be sure to check out my weekend guide! As always, feel free to leave any questions in the comments below too!
Like this post? Pin it to save it for later and share with others!