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Boston Travel Guide: The Spots I’d Take Someone Who’s Never Been Here
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items A little Boston guide with the places I’d actually take someone visiting for the first time. Classic Boston spots, good food, cute cafés, shopping, photo spots, hidden gems, and a few places that are easy to miss.
Map
Sections
5
Classic Boston
Food
Photo shoots
Shopping
Hidden Gems
Classic Boston
Such a pretty little bookstore and café on Charles Street. I’d go here when you want to wander around Beacon Hill and have somewhere cozy to stop.
Beacon Hill Books & Cafe
The Boston classic. The line can be ridiculous, but if you're visiting the North End for the first time, I'd still say it's worth getting a cannoli here.
Mike’s Pastry
A very Boston stop if you want a lobster roll without making it a whole fancy dinner. And it’s right on the waterfront.
James Hook & Co
Bookstore downstairs, café upstairs, and right on Newbury Street. I’d definitely add this to a slow afternoon of shopping and wandering around Back Bay.
Trident Booksellers & Cafe
One of those stores you can walk into with no plan and somehow spend 30 minutes looking at everything. Good for records, comics, random gifts, and Boston souvenirs.
Newbury Comics
One of those places that feels very old-school Boston. Go for seafood and the history of the place as much as the food.
Union Oyster House
Food
Dumplings with fun New England-inspired fillings, so it’s a little different from the usual Boston food stops. Definitely one to try with friends when you want something quick and not too serious.
Mei Mei Dumplings
An old-school little sub shop in the South End that feels like the kind of place you stumble across and end up going back to. Good pick for a cheap, easy lunch.
Billy's Sub Shop
This is such a good little breakfast spot when you want something quick but actually filling. Their breakfast sandwiches are the thing to get, and it’s an easy stop before exploring the city.
Mike & Patty's Bay Village
Photo shoots
This is fully a Pinterest street. The brick, little houses, and narrow street make it one of my favorite places for photos around Beacon Hill.
Acorn Street
The courtyard is gorgeous and gives you a completely different look from the usual Boston brick streets. An added bonus for those named Isabella is its free!
Isabella Stewart Gardner Museum
Shopping
A cute little shop for gifts, candles, jewelry, and random things you’ll probably want even if you walked in with no intention of buying anything. It’s also an easy stop while walking around Beacon Hill.
FLAT OF THE HILL
A good place to look for secondhand clothes without having to dig through racks forever. You can find everything from everyday pieces to nicer designer stuff, so you never really know what you’ll find.
Covet Boston. Curated Secondhand and Vintage.
One for when you actually want to go vintage shopping instead of just browsing a cute boutique. They have a really good mix of clothes, jewelry, and accessories, especially if you like finding pieces that feel a little different.
Vivant Vintage Allston
This one is definitely more unexpected — it’s a family-run shop with leather goods, boots, jackets, and western-style stuff. Even if cowboy boots aren’t your thing, it’s a really fun place to look around because it feels completely different from the...
Helen's Leather Shop
Hidden Gems
A huge outdoor art space underneath the highway covered in colorful murals and street art. It’s a really fun place to wander around and take pictures without feeling like you’re at another tourist attraction.
Underground at Ink Block
This tiny North End shop is packed with coffee, spices, and all kinds of Italian grocery finds. It feels like one of those places you could walk right past if you didn’t know it was there.
Polcari’s Coffee
A record shop inside an old firehouse in Allston with records packed basically everywhere. You have to actually dig around, which is half the fun.
Looney Tunes
Tucked into the Fens, this feels surprisingly far removed from the city even though you’re still in Boston. It’s especially pretty when the roses are in bloom and makes for a really peaceful little escape.
James P. Kelleher Rose Garden
A tiny Beacon Hill record shop that’s especially fun if you like digging for music you’ve never heard before. They have a really curated mix of rare, weird, and older records, so it’s worth taking your time and looking through everything.
Music Research Library