9 Non-Touristy Things You Absolutely Must Do When Visiting Boston

Courtesy: Bostonusa.com

When I visit a new city I like to experience it like the locals do. Rarely do I opt to visit/experience a tourist attraction, frankly because I know it’s just that! I’d much rather walk like the locals, talk like the locals and play like the locals – it’s way more fun.

Having lived in Boston now for eight years (time flies!), I often get asked “what should we do in Boston?” from people that are visiting the area for the first time, and while I have some good options, I’m still learning, too! I feel like I find a new hidden gem every time I set out to explore what Boston (and its surrounding towns) has to offer. So, I thought it fitting to tap into the locals for some additional insight.

Here are the top nine things to do when visiting Boston – straight from Bostonians themselves.


Summer Thursdays at the ICA 

Courtesy: weekendpick.com
“While the Modern Art might be hit or miss on Thursday nights at the ICA in the summer, there’s free music (world class musicians, alumni from the Berklee College of Music), an outdoor bar, food and an incredible view of the harbor. Makes for a perfect outdoor picnic.”
Sean McGrail, co-founder of Paint Nite 

Explore Eastie

Courtesy: Kelsey Converse, @tinytravelerblog
“One thing that I’m in forever awe of is the view from East Boston. You can either grab a delicious cocktail at ReelHouse and take in the views from there, or grab a cider at Downeast then head to Piers Park for one of the best views of the city. TIP: in the summer, there’s a free ferry to and from Reelhouse and Pier 6 (in Charlestown) so you can easily hop on to get to either spot.”
–  Kelsey Converse, travel blogger at The Tiny Traveler Blog 

Sip a Caipirinha at Yvonne’s

Courtesy: Sunrise-villa.com
“Visit Yvonne’s in Downtown Crossing and ask for Bruno. Tell him you want a traditional Caipirinha. It’s hard to get the cocktail made the right way and Bruno knows how.”
– Emily Burns, Lifestyle Publicist

Take a Peak Inside Fenway Park – From a Bar Stool

Courtesy: Bleacherbarboston.com
Fenway is one of my favorite Boston neighborhoods – I just love the vibe! It’s super laid back, and non-threatening, though vivacious at the same time. If you don’t have the opportunity to actually attend a game at the ballpark, head into Bleacher Bar on Lansdowne Street. It’s the only place that has a view of the park from the inside. Sports fan or not – seeing inside America’s oldest baseball stadium from the comfort a bar stool – cold beer in-hand – is a pretty cool experience.
Me, lifestyle blogger + owner of CKO PR  (shameless plug 😄)

Grab a Sandwich from Kelly’s Roast Beef

Courtesy: Natick Patch

Kelly’s Roast Beef is a New England staple. Hop on the Blue Line (T) and get off at the “Wonderland” stop. Grab one of Kelly’s legendary sandwiches and enjoy by the ocean.

Tasha Bracken, owner of SD Events

Visit Brattle Book Shop

Courtesy: TheNewEnglandLife.com

“When visiting Boston, I recommend a stop at the Brattle Book Shop. It’s hidden in an alleyway off of West Street, right near the Boston Common. The historic indoor and outdoor shop is a book lovers dream, where you can find classics, like a 140-year-old Charles Dickens book sitting on the shelves, for just $5. Plus, it’s the perfect photo opp, with its unique oversized pencil as a store sign, the outdoor bookshelves, and art murals.”

Robbin Mangano, lifestyle + travel blogger at The New England Life

Wine + Dine on Tremont Street 

Courtesy: AmericanInno.com
“Go walk, dine and drink on Tremont – a wide, tree-lined street in the historic South End with fantastic restaurants lining the blocks from Berkley to Brookline. Grab a glass of wine from The Butcher Shop, catch some Jazz at The Beehive, and eat at Frenchie (best Brussel Sprouts EVER).”
 Krista Paton, co-owner of Urban Axes (opening in Boston this summer!)

Kayak on the Charles

Courtesy: Kali Hawlk @kalihawlk
“For folks who come to visit in the warmer months, kayaking on the Charles is a really fun way to experience the city. It gives you such a different perspective – and getting to do something a little adventurous and very outdoorsy in the middle of the city is a really fun and unique activity that most folks visiting don’t usually consider.”
– Kali Hawlk, finance + lifestyle blogger at Going Beyond the Wealth

Find the North End’s Hidden Deli

Courtesy: Patricia Camerota @ConPiccoliPiedi
“When in the North End, people usually run toward Mike’s or Modern Pastry only to wait in a heinous line for a cannoli that I would argue isn’t Boston’s best. Instead, people should start their foodie adventure in the North End at Bricco’s hidden deli. It’s down a tiny alleyway (marked by a sign that’s easy to miss) right near the entrance of Bricco’s main restaurant.
Inside the hidden deli there is an abundance of delicious imported Italian foods, including a large metal bowl filled with octopus soaking in oil that sits on display—my favorite. After marveling at the gastronomic goodies, head to the counter and order the Porchetta sandwich, it will transport you to Italy. Once you’re finished, grab your cannoli over at Maria’s, a family-owned pastry shop where celebrity chef and writer Andrew Zimmern visits whenever he’s in Boston.”
Patricia Camerota, food + travel blogger at Con Piccoli Piedi 

Feature photo courtesy of Bostonusa.com.

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