Boston is a very Instagram worthy city, from the scenic historic streets to quirky hidden gems, there is plenty to choose from. Whether you are trying to capture a laughing candid, show off your adventurous side with images from your explorations, or simply encapsulate how much fun you have had at classic Boston attractions, we’re all searching for the best place to take that Instagram worthy shot. Here’s a top-five list of where you should visit, according to a Boston Old Town Trolley expert and a current Boston resident.
One of the most popular locations in the city, and in the country, is Acorn St located in Beacon Hill. Easily accessible from T stops like the Charles/MGH and Government Center, this area is best visited by foot since street parking is hard to find. This charming little street has made its way onto many lists of Instagram Worthy places and is the most photographed street in the United States. Known for beautiful cobblestone streets and grand brick buildings, Beacon Hill transports you to the old days of Boston. This is the perfect backdrop to show off your #outfitoftheday or Instagram the historic vibe of the city. Local expert and Old Town Trolley employee Iryna Cordero even discovered a beautiful ivy colored wall while exploring the neighborhood.
“I saw this five-story building as I was walking through Beacon Hill and was amazed by the ivy that had taken over the entire wall,” Iryna noted. “I had to stop and take a picture. I’d recommend walking through this area in the fall, the streets and plants come alive with color that time of year.”
Another spot that’s beautiful in the Fall is Faneuil Hall. Easily walkable from the Aquarium, Haymarket or Government Center T stops, Faneuil Hall is great place for tourists and locals alike. If you’re driving, there’s even discounted parking at the 75 State St Garage. The trees that line the walkway change color and add a touch of nature in the otherwise bustling city, especially as you walk the brick paths and feel the crunch of the leaves under your feet. So do a little shopping and grab a pumpkin spice latte for a seasonal shot under the trees. If you’re visiting in the winter for some Christmas shopping, the giant Christmas tree is a must-see. Plus, every half hour there is a light show along with festive music that is fun for families and the perfect Holiday photo opportunity.
“Early morning before the tourists come is the best,” According to Iryna. “And when it does start to get crowded, you can head towards the long wharf. There’s a magnificent view of the water and you can see the boats coming and going.”
Another Boston classic that certainly can’t be ignored is the North End. Conveniently close to Faneuil Hall, just head north or get off the T at the Haymarket stop. Full of amazing restaurants, delicious pastry shops, and lovely cobblestone streets that lead to the water, this is a must-visit area for anyone looking to explore all that Boston has to offer. To elicit jealousy both on the streets and on the 'gram, walk around with a Mike’s pastry box and the comments will be nonstop.
“It’s become a tourist favorite, but Mike’s is delicious,” Iryna commented when asked which North end spot she recommends to friends. “Their cannoli are amazing.”
To avoid the long lines and try something other than cannoli’s, I would recommend Modern Pastry on 257 Hanover St. You can still run into an after-dinner rush of people looking for something sweet, but the line brings you past all the counters filled with pastries, cupcakes, and Italian cookies so you have plenty of time to decide. 
When it comes to views of the water, the Seaport is Boston’s newest area for breathtaking views. With shops and dining options popping up as the neighborhood expands, there always seems to be something new to explore. Iryna’s favorite has always been the ICA, where there is a fantastic view of the water from all glass windows that line the back of the art showrooms.
If you’re driving the One Seaport Garage is available along with Street parking. Or, you can walk from the Broadway stop in South Boston. Personally, while I was walking from the South Boston to the Seaport, I discovered a hidden gem in an overpass along A Street that transforms into a Rainbow Bridge at night with hundreds of colorful string lights. It’s these kinds of secret little spots that make the Seaport such a fun place to visit.
Speaking of secret sites, Downtown Crossing is the ideal place to 
find tucked away shops. Easily accessible by car since there are several parking garages nearby and a T stop located in the heart of the shopping, this is a entertaining place to spend a day or a couple hours.
A personal favorite of mine is Brattle Book Shop at 9 West St. With 3 stories of used books and magazines, along with rare 1st editions, you’ll lose yourself browsing for your next beach read or conversation-starting coffee table book. In the warmer months, the books find their way outside to the open lot next to the shop. This artsy alleyway photographs wonderfully, and the best part is it’s full of fantastic markdowns.
By Digital Content Coordinator, ARIANA JENNELL
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