Boston, MA City Guide

by Sabrina Smelko

Boston, MA City Guide

After graduating from college in 2007, New England native Lauren Wells moved to the west side of South Boston with her then-boyfriend/now-husband, Matt. Over the years, they’ve watched developing neighborhoods emerge — including their own — and have enjoyed being a part of the ever-changing landscape.

As Creative Director and founder of her own firm, Lauren often travels for both work and play, but she is grateful to call this four-season, East Coast city her home. From its walkable streets and historic sites, to its world-famous marketplaces and attractions that rein in over 12 million visitors each year, this proud capital of Massachusetts has a lot to offer, and today, Lauren is sharing just a taste of it. –Sabrina

Photography by Lauren Wells


First up, tacos and guac! Border is a staple, right in Harvard Square. Bottomless chips, the best empanadas, and frozen strawberry margaritas — all for under $40.

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Loco in South Boston is a favorite of just about everyone who walks through their doors. Ceviches, oysters, fish tacos and coconut margaritas — not to mention the best service.

In Somerville, The Painted Burro is another favorite, with the most daydream-inducing nachos, an eggy chorizo taco that is heaven, and an amazing brunch menu as well. Be sure to get the horchata iced coffee if you visit!

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Speaking of brunch, two spots we frequent are Tatte Bakery (the muesli and the shakshuka, please), and Rosebud Kitchen. Oh, Rosebud Kitchen. It’s everything brunch should be, from the DIY bloody mary bar to the griddled breakfast sandwich to the blueberry-stuffed pancake. Toro and Puritan serve great brunches, too.

If you are on the run, there is nothing like a South End Buttery bacon, tomato, egg and cheese on a biscuit. Unless, of course, you pair it with one of their blueberry-lemon scones. Perfection!

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Now, onto coffee and cocktails! Thinking Cup on Newbury pours the best hazelnut latte around, while The Coffee Trike is great for a midday pick-me-up. Newly opened Gracenote by South Station is a beautiful spot to check out as well.

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Loyal Nine in Cambridge is my absolute favorite — reminiscent of the open-air coffee shops in Chiang Mai, it is the dreamiest place to sit, work and sip all day. As for cocktails, Drink, Shojo, Trade and Alden & Harlow continuously impress, with inventive drinks and beautiful presentation. If you are a wine enthusiast, be sure to visit Belly in Kendall Square — and roast a s’more while you are there!

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A few favorite dinner spots include Sarma (go with friends so you can order as much of the menu as possible), Island Creek Oyster Bar (their sister restaurant Row 34 is equally splendid), and Menton (fine dining at its finest).

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There are a few casual favorites that we dine at regularly, and they are all sorts of wonderful. Picco in the South End has wood-fired pizzas and homemade ice cream, with an extensive beer list to boot. Myers + Chang offers modern Asian cuisine, served dim sum style with mouthwatering flavors. And lastly, Cafe Jaffa is a tiny gem in Back Bay, serving Middle Eastern dishes and giant vats of “sangria for two.”

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Notable new mentions go to Townsman, Coppersmith and Hojoko, all of which opened their doors this year. It is always exciting to try new places and to add new favorites to the list!



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My favorite neighborhood to shop and stroll is Beacon Hill. There are plenty of boutiques along Charles Street, such as Good (unique, beautiful gifts), Crush (my favorite women’s clothing boutique), Dress (they carry a number of great brands, including Clare V. and Ace & Jig), and December Thieves, offering all sorts of amazing accessories and high-quality finds.

The South End is great for small shops and boutiques as well. Sault offers a great range of menswear and gifts for men, while Niche offers everything you need for an urban garden oasis. Olives & Grace sells food gifts and small goods from domestic makers, and Follain is an organic beauty haven, with the most simple and stunning store design.

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Farm & Fable is the one-stop shop for foodies and culinary collectors, and you can even attend events in the beautifully designed kitchen below the store. Pioneer Goods Co. is another don’t-miss shop, with furniture, home accessories and antique finds. And lastly, Hudson is a fantastic home store, with small accessories and larger pieces of furniture that are both classic and unique.

Harvard Square is another great area to explore. Mint Julep is the best for cocktail dresses and pretty frocks, while Leavitt & Peirce is a tobacco, gift and game shop. Black Ink has all sorts of gadgets and gizmos to delight, and there is an honor-system bookstand right on Brattle Street that is perfect for perusing.

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Boston has plenty of farmers’ markets, with Copley Square and the Greenway hosting two of the best. Pick up fresh fruit, locally grown veggies and handfuls of wildflowers.



Verb Hotel

The Verb Hotel is one of Boston’s newest spots, right in the midst of Fenway. With a mid-century vibe and an outdoor pool, it can’t be beat.



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The museums in Boston are exceptional! From the MFA to the ICA to the Isabella Stewart Gardner, there is art for everyone. Each of those museums have monthly cocktail parties, so be sure to check the calendar before you visit. ICA First Fridays on the harbor are a blast, with DJs, summer cocktails and an Island Creek Oyster raw bar. Another museum that flies a bit under the radar is the Harvard Museum of Natural History. There are two exhibits which always blow my mind — the rocks/minerals and the glass flowers — but the whole museum is worth exploring!

No trip to Boston would be complete without stepping into the Boston Public Library. It is a storied building, pun intended, and so magnificent.

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You should also be sure to wander through the Boston Public Garden, the first public botanical garden in America.

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Get out on the water! Whether you rent stand-up paddle boards for the Charles or Fort Point Channel, charter a sailboat from the Boston Sailing Center, or embrace being a tourist on a Duck Tour, be sure to view the city from the sea.

If you are looking for a fun activity, try a cooking class at Stir, have a picnic at the Arnold Arboretum, visit the SoWa Open Market, or head over to Lawn on D for what is sure to a fun-filled day under the sun.

Is it raining? Catch a movie at one of Boston’s many local theaters. Brattle Theatre and Landmark Theatres, a Kendall Square Cinema, show a wonderful selection of films, with freshly popped popcorn and Boylan natural sodas.

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And lastly, leave the city! One of the most tremendous things about Boston is you can drive two hours in any direction, and you will end up somewhere crazy-beautiful and quintessentially New England, such as Cape Cod, Vermont, Maine or The Berkshires.

Suggested For You


  • This is a great roundup of Boston favorites. I hate to admit it but living in Rhode Island and being 5 minutes from Providence does make going into Boston seem so daunting!

  • I’m from Boston and we may have Mexican restaurants but I really wouldn’t recommend them if you’re expecting good Mexican food. So I was surprised to see places like Border on here…

    • I’m from Boston and I feel the exact same! The only place I ever get mexican here is el Pelon, which is actually great but probably not fancy enough to make this guide

      • I thought the exact same thing re: Border (all praise & glory to El Pelon!). That aside, there are some other really great restaurants on this list. If you can’t get a table at Island Creek – which is likely – Eastern Standard just down the block is run by the same hotel and is also excellent.

        • I’m late to the game, but seriously, if you really need tacos in Cambridge try Naco Taco in Central Sq. or Lone Star Taco Bar. But if you’re hungry in Harvard Sq. you’d be better off walking up Mass. Ave. to the exceptional Giulia for some sensational Northern Italian food or staying on at Alden & Harlow for dinner after your drinks! Night Market is a great casual choice in Harvard Sq., with inventive asian street food small plates in a very funky underground space. (Plus Sake Slushies!!) Area Four in Kendall or A4 Pizza in Somerville are terrific, Puritan & Co. has a great space and intriguing menu, and we have new places opening all the time: BISq and Shepard are both promising new additions to our awesome neighborhood.

  • LOVE, LOVE, LOVE this list!! I cannot get enough of SoWa, the Gardner and the library. Border is my ABSOLUTE favorite restaurant, I go there at least twice a month – amazing drinks & yummy food in a super fun neighborhood! Have to check out the rest of the recos too!!

  • Great city guide!!! I can tell you put a lot of work into it and I am so excited to check all of the places out. Thanks Lauren and Design Sponge!

  • We just returned from a weekend in Boston and stayed at The John Jeffries House http://www.johnjeffrieshouse.com While it is NOT hip like The Verb, it is so convenient and so very reasonable. Very clean, rooms are good size, and all (I think) have some sort of kitchen! All for about half the price of any other Charles St./Beacon Hill hotel!

    • We also stayed at John Jeffries House in August. Great deal and so close to Beacon Hill, Harvard and the T is across the street. The staff could be a little more friendly, but otherwise no complaints.

  • Push beyond south Boston, the south end and Beacon Hill and you’ll enjoy wonderful food in Boston’s other neighborhoods. Ali’s Roti on Blue Hill Avenue has the best West Indian food. There is a second location on Columbus Ave in Lower Roxbury. A short ride on the blue line and you’ll be in sunny Chelsea where just about every restaurant serves the yummiest pupusas. Want great takeaway food, check out Cityfeed and Supply in Jamaica Plain, grab some sandwiches and snacks and head over to JP pond or the arboretum.

  • Great picks! Glad you mentioned Shojo, it’s a really cool spot. Neptune Oyster in the North End is another fantastic spot…. go early though, they often have a long wait.

    • If you can take the train out of the city, take the Worcester line to Wellesley Square station. The town center is fabulous with great restaurants, such as Ming Tsai’s Blue Ginger, or the more affordable Juniper. Wellesley center is also about a mile walk from Wellesley College, which has beautiful Hogwarts-like architecture. The Wellesley town hall also has a cute pond where geese and other birds hang out. The whole area is great for a day or afternoon of walking and exploring.

  • I’ve lived here most of my life and I wouldn’t mention anything on this list really. It’s all swanky! Boston has some great and beautiful spots like the Emerald Necklace and the Fens. Theres so many more affordable friendly places I would list.

    • seriously! Its a good list, but only if you’re made of money. I’ve lived in Boston (JP) for 10 years and maybe would have only mentioned some of the cocktail places.
      Not even a mention of Union Square and all its wonderful restaurants and shops, or Centre St. in JP. Even in town, don’t forget about Flat Black and Cuppacoffee for good cafe’s.
      Lest we forget the wonders of Chinatown and the best vietnamese food in the city; in Fields Corner, Dorchester!

      • Alex

        It’s hard to get everyone’s picks in one guide, but we welcome any additions you’d like to shout out. I love JP and have friends there, so I’d love to hear your favorite spots.


        • JP is my hood! We love Tres Gatos for tapas and yummy wine. Of course, their record/bookstore in the back cannot be beat! Their sister restaurant Centre Street Cafe is insanely good and a few blocks down the street. Chilicates, a new taco/burrito place has great food, less expensive, totally casual, and great when you’re on your way to the Sam Adams Brewery. Man, I’m thinking there should be a Jamaica Plain guide… :)

  • I would throw in Backbar in Somerville for cocktails and small bites! Great cozy spot with excellent drinks and staff.

  • Sorry to be a buzz kill but picnics are NOT allowed in the Arboretum except…..possibly…..on Lilac Sunday. The Rose Kennedy Greenway is also a wonderful green space right in the middle of the city and borders the waterfront.

  • I concur. Boston is not the place for Mexican. We’ve got great food, but Mexican isn’t a strength (unless we’re talking Olecito’s Baja Shrimp Tacos in Inman Sq). Come try the Dominican & Haitian food.

    Also, Border Cafe is a chain, branded as Jose Tejas. I really don’t understand the love affair. My sense is its mostly college kids from Harvard and tourists eating at the Mexican version of TGIFridays.

    But, HIGHLY recommend the Boston Public Market- our new indoor market of local produce and prepared foods. Right near the Rose Kennedy Greenway (go visit the Labyrinth in the Armenian Memorial Park, and the Carousel with New England animals!), a perfect picnic spot before crossing into the North End or Chinatown!