5 THINGS: A Travel Guide to Boston


In “5 Things,” I’ll ask some of my favorite bloggers in cities all over the country to share insider travel tips on where to eat, shop, stay, and play in their neighborhoods (plus, what to pack to make the adventure complete). This week, Anna Burns of Dear Friend shows us what’s not to be missed in Boston.

5 Things: Boston
Anna Burns of Dear Friend

It’s no secret that Boston is my favorite city. I moved here just after graduating college—almost 10 years ago to be exact—and I haven’t looked back since.

Just two hours from Portland, Maine, and even less to parts of the Cape and Rhode Island, you could easily find yourself enjoying a day trip to the beach in the summer or hiking the White Mountains of New Hampshire in the fall.

The city of Boston is known for being the walking city—most areas are completely accessible by foot or by train, and if you’re in a pinch, there’s always an Uber around, too. We’ve got great history, the best seafood, and, without a doubt, charm and beauty at every corner (if you know where to look).




Neptune Oyster, 63 Salem Street, (617) 742-3474

When in Boston, eating seafood is a must. And oysters? The best! Try Neptune Oyster on Salem Street in the North End for the coziest, most delicious dinner this side of the Charles River. With only a handful of tables and a bar that’s always packed, the wait for this place can certainly be significant—but it’s worth it! Put your name in, walk around Hanover Street, get yourself a cannoli (Modern Pastry is my personal favorite), or a drink at Bricco or Lucca. Then come back to Neptune when a seat opens up (they’ll call you on your cell to let you know). Once inside, enjoy the warm light and a glass of wine, then decide which dishes strike your fancy. I highly recommend the buttermilk johnnycake and the hot Maine lobster roll. Everything is just so good—you will absolutely love this place.





Follain, 53 Dartmouth St, (857) 284-7078

My favorite place to shop is Boston’s South End, which is home to many local artisans, small shops, and vintage goods. I always make a stop at Follain when I’m in the area, picking up healthy skin care products in the most gorgeous light-spattered space on Dartmouth Street. While you’re in the neighborhood, you’ll also love SOWA Open and Vintage Markets, Olives & Grace, and Pioneer Goods. Grab a coffee and a cupcake at The Buttery if you’re around in the afternoon, or a drink at The Beehive while you listen to some jazz closer to dinnertime.







Airbnb — Beacon Hill

Beacon Hill is one of the loveliest neighborhoods you’ll find in Boston—and one of the most historic, too. The above apartment is my friend Rachael‘s, nestled right on Chestnut Street. It’s a place we were lucky enough to stay at this summer while she and her family were out of town. In Beacon Hill, you’ll find brick-lined sidewalks, gas-lit street lamps, and some of the most gorgeous old brownstones in the city. While you’re there, be sure to walk the length of Charles Street (find Acorn Street if you can!), eat a meal at The Paramount, and meander through the Public Garden and Boston Common. End your adventure at Brattle Book Shop, an outdoor bookstore that’s sure to make you smile.

(If staying in a hotel is more your style, try the Beacon Hill Hotel & Bistro or The Liberty Hotel, for reasonably priced rates.)






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The Charles River Esplanade, Back Bay, on the banks of the Charles River

Skywalk Observatory, Prudential Center, 800 Boylston Street, (617) 859-0648

Boston Public Library, 700 Boylston Street, (617) 536-5400

There really are endless sights to see while you’re visiting Boston, but my favorite days are those spent walking or biking along the Charles River (rounded out with a visit to the Boston Public Library). For the best, most stunning views of the city, visit the top of the Prudential Tower where the Skywalk Observatory is open daily and offers a birds-eye view of each neighborhood, including Fenway Park and the famous CITGO sign. If you do visit the library, be sure to step into the Reading Room—and if it’s a warm summer day, sit out in the courtyard with a book. It’s such a happy place to be.



down jacket, $89.90, a camera, and a leather tote, $168

These photos of Boston are full of warmth, but don’t let that fool you into thinking it’s always sunny here. Boston’s winters are cold and windy, so come prepared with lots of layers and a warm coat, too. A down jacket like this one is keeping me cozy these days, and I never go anywhere without my favorite tote and, of course, my camera. Don’t forget yours—there’s so much beauty here, you’ll want to capture it all!

Thank you so much, Anna! I’ve only been to Boston once: Aron was interviewing for residency and we took a train from New York. I remember carrying a bouquet of baby’s breath on the train and then walking the Freedom Trail through snow drifts in our ill-advised, California-level jackets. We warmed up over incredible pizza and marveled at the history. I’d love to visit again!

All photos by Anna Burns. As ever, thank you to Shoko Wanger for her help with this series. Find all entries in the 5 Things series

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