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Guest Blogger Series: A City Girl's Guide to a Weekend in Boston

This month we are featuring guest blogger Vanessa from The City Girl's Guide ! She knows the city well and offers up some of her best tips to get to know the city and make your travel easier.  Let us know your thoughts by leaving a comment below. 


Being a city girl means that I've experienced Boston from sunrise to sunset. This means a lot of brunches, lunches and made-up meals along the way. But as with any city, the options can be overwhelming and it's often hard to know where to go to have not just a meal or a good time but an experience.

If you're visiting Boston for the weekend, making the most of your time is key & I've rounded up some of my favorite spots to dine, drink & discover in my favorite city:


Flour Bakery / Kristin Teig

Breakfast | Flour Bakery & Cafe (multiple locations): If you're looking for a spot where you have the option to sit down or do grab-and-go, Flour has got you covered. Their pastries, cookies and coffee are perfect for a quick bite or a mid-afternoon snack. Croissants, sticky buns and hot chocolate are all favorites here.

South Street Diner: Also a fantastic late night option, South Street Diner is famous for comfort food, crispy bacon and a certified retro vibe. I have a hard time finding a diner this authentic not in the city so I consider this spot a real gem. It's worth noting that my first experience here was for Mardi Gras and the complimentary beads, mimosas (yes, for dinner) and crawfish did not disappoint.

Honorable Mention: Thornton's: Thornton's was a college haunt for me and it remains to be an ideal breakfast-ing locale. You can't go wrong with sweet or savory here and the quaintness of it feeling like a neighborhood spot earns it points where it lacks in being a bit off the beaten path.


@tablefor2cities | Cuban Sandwich

Lunch | Sam La Grassa's: A day of doing tourist-y things can lead to a big appetite which is what you'll need if you venture here for a sandwich. There's no need to order sides (unless you're sharing and want the full experience) but if you do, the fries and slaw are a treat.

Abe & Louie's: This is a great sit-down spot in the middle of the action. A cozy and familiar menu with the comfort of being near some fabulous landmarks make sit so that you don't need to feel rushed by a crowd or plan your next move in a hurry. Their bar bites are the perfect choice if you're stopping in for a late lunch or early dinner and the surf and turf options will please almost every palate.

Honorable Mention: Quincy Market: If you just can't decide (or want smells of everything before you do), Quincy Market is an impressive option that is packed during prime hours for a reason. You can try the Boston-famous, fresh and hot Regina Pizzeria or sip on a cool, tropical smoothie from The Monkey Bar. But whatever you do, don't leave without getting (at least) a half dozen cookies of your choice from The Boston Chipyard.

Credit: Island Creek Oyster Bar (Boston) | Lobster Roe Noodles

Dinner | Island Creek Oyster Bar: Until you've had seafood in Boston, you haven't really lived. Sure this place has seafood from all over but the folks here really know their stuff. The ambiance is warm and glowy so you could definitely come here with a crowd or with a significant other. It's a bit on the pricier side but once you try the lobster roe noodles or a tasting of freshly shucked oysters, you'll be a believer.

Eastern Standard Kitchen: Somehow two of my favorite dinner restaurants are within a block of each other but their vibes are different enough that I think they both deserve to be on your list. If Island Creek is the expert on seafood, consider Eastern Standard to be the master of cocktails. Many of the items on the menu are familiar enough that you'll feel comfortable enough to tell the bartender to surprise you.

Stella | This South End spot is seriously chic. The all-white decor is minimalistic but refreshing and helps you enjoy your company and grilled pizza without distraction. Pasta dishes here are my personal favorite and they also offer a late-night menu from 11pm-1am.

Honorable Mention: Citizen Public House & Oyster Bar: This place can double for a good spot to grab a nightcap but come for the charcuterie and stay for the cocktails. I've also been known to frequent here for brunch as the Huevos Rancheros are enough to make me want to drive from 40 minutes away to meet friends.


Credit: @juliaedom

Nightlife | Harpoon Brewery: I've never met a brewery I didn't like and this one has pretzels so I've all but inquired about what it would cost to live here. I will admit, I've never been here for their famous "HarpoonFest" but if you like beer and a great venue to be social, this is a good place to start.

The Hawthorne: For more of a grown-up venue, The Hawthorne has Gatsby-esque vibes with great small bites for sharing. The decor is pretty luxe so I consider this to be a good spot if you're looking for a few more rounds before calling it a night.

Honorable Mention: Warren Tavern: If your travels take you to "The Town", I highly recommend stopping in here to experience the epitome of cozy. Whether for dinner or a night out, the space is inviting and is housed in the exact spot where Dr. Joseph Warren of the American Revolution once lived. 


Credit: BSO

Things To Do | Boston Common/ Boston Public Garden: Some visitors crave the great outdoors and I believe that you'll miss a lot of Boston if you spend all your time indoors, at museums or in and out of the shops on Newbury Street. The Boston Common and Public Garden are centrally located and feature food trucks, a fountain, skating (or a wading pond depending on the season), botanical gardens and the picturesque swan boats that were basically made for Instagram.

Rose Kennedy Greenway: Another outdoor site you won't want to miss is this open space situated between The North End and Waterfront and Downtown Boston. There are plenty of installations to enjoy, benches to plan your next move and tables to enjoy treats from a nearby food truck. Weather permitting, it's also fun to enjoy a picnic lunch on the grass or simply take in the scenery.

The Esplanade: For a gorgeous view of both Boston and Cambridge, you'l want to head here where the Charles River divides both cities and lays the foreground for the crew teams, sailors and paddle boarders. Perfect for a morning run, romantic walk or scenic egress to your next destination, The Esplanade also home to the Hatch Shell where fun performances take place during the warmer months.

Symphony Hall: If you like the arts, meet the home of The Boston Symphony Orchestra. Inside, the space is truly regal and makes you feel incredibly small. I have fond memories of coming here as a little girl and remember thinking for the first time that "fancy" was an understatement.

Fenway Park: Whether you love them or you hate them, there's something to be said for the Red Sox calling "America's Most Beloved Ballpark" home. They serve Guinness on draught, have phenomenal tours and I haven't gotten to how fun it is to watch a game here yet...