One Weekend in Boston

After spending six years in Boston, I am taking a hiatus in Italy. Coming back for the holidays though, I’ve realized that I never wrote anything about my favorite city in the world re: what to really visit while you’re here (if you’re looking for a list that includes the Freedom Trail in its entirety, search elsewhere). It’s heavily food-centric, but nevertheless, check out my idea for a fun weekend in Boston AND Cambridge, REGARDLESS of the season you’re visiting in!


Friday (evening):

Assuming you spend half a day getting to Boston, a great way to spend Friday night is at a local restaurant and lounge. (Hopefully you have found a hotel or AirBnB near an MBTA train line!)

FOOD: My favorite restaurant in the city is Lolita’s, a Copley Square tequila bar that recently opened a second location in the Fort Point/Seaport neighborhood. A reservation can be difficult to get here, especially at the original, smaller Copley location, so plan ahead and reserve online.

TO DO: If you don’t get a reservation, and you’re willing to wait the traditional 2-hours, I recommend the Copley location as it’s between Newbury Street and Boylston, which both have many high-end shops to visit during that time, and Copley Square is home to both the finish line of the Boston Marathon (see if you can find the bricks with the winners’ names inscribed each year), as well as as Trinity Church, beautifully reflected in the John Hancock Tower. If you have time, visit the Boston Public Library at Copley. The new and old parts of the library are separated by a courtyard, and the 2nd floor of the McKim (old) building, namely Bates Hall, is impressive to see. All of this would be great to do during the day as well, if you arrive earlier to the city.

Back to FOOD: When you finally get to dinner, you’ll find that the dark decor at Lolita’s is lightened when you sit down and the server brings your table a gratis treat. The broken heart margarita is superb, and the food is tasty, if a little expensive. Upon requesting the check at the end of your meal, expect another sweet (and complimentary) surprise! Each location as a few bars inside as well, if you’re not looking to sit down. Bostonians are not known for going out with the intention of meeting new people (we like to catch up with existing friends instead), but everyone has a unique opinion on the city and won’t say no if you ask them to chat about it. You could easily spend a whole evening here, but if you’re looking for a more traditional bar after dinner, the Copley location is surrounded by various Irish bars, and the Fort Point location is walking distance from Lucky’s Lounge, a small but lively venue with both a sit-down area and a dance floor, with live music after 10pm.



FOOD & TO DO: Saturday morning should be spent at the Boston Public Market, located inside the same building as the Haymarket MBTA Station (it’s above the station, so you have to exit the station and walk to the corner to enter the Market). There are wonderful breakfast options (I love the Shakshuka from Inna’s, as well as the bagel sandwiches from The Bagelry), along with many local and handmade gifts.

If the food options at the Public Market aren’t broad enough, you can wander down the street to Faneuil Hall & Quincy Market. Faneuil Hall is famously lined with dozens of food counters, where you can get anything from traditional clam chowder, to candied apples. My favorite stop is the new(ish) Magnolia Bakery, right at the beginning of the hall. Magnolia is transplant from NYC, and you can get the world’s best banana pudding there! (NOTE: If you’re ever looking to get a full sit-down meal near Faneuil Hall, Zuma’s (on the outer side of the hall, downstairs) is the best and most (only?) affordable option!).

TO DO: Alternatively, nice weather can mean the walk toward Boston’s North End (the Italian neighborhood, search for Hanover Street), can lead you through part of the Greenway (a nice park to rest, with water for kids to play in in the summer), or toward gelato, cannolis, and pizza (Regina’s is known to be the best here, although Boston is not a pizza-centric city and can’t compare to NYC). You may see people walking around with Mike’s Pastry’s boxes, but the cannolis at Modern Pastry are better and the wait is never as long. If you stumble upon a bocce court, you may be standing in the location of the great Molasses Flood (it was exactly what it sounds like; 21 people died).

If you’ve chosen the Faneuil Hall route, there are many international shops (Uniqlo, Ghirardelli, an abnormally large Crocs store, etc). History buffs will enjoy the area, which is a stone’s throw from City Hall (Government Center), voted many times the world’s ugliest building… as well as the beautiful Old State House (where there are stones marking the location of the Boston Massacre, although the exact location was actually a bit off from there). The golden lion on the top left of the Old State House was actually a time capsule that the city opened for the first time last year.

From there, it’s worth walking up to Cambridge street, turning left toward Park Street Station (although if you have a daily or weekly pass for the MBTA you could technically take the train). Along the way you’ll see the King’s Chapel Burying Ground (the oldest in the city, circa 1630), the Omni Parker House (the hotel that claims to have invented Boston Cream Pie), and the Granary Burying Ground (where you’ll see many familiar names). Note that burying ground means that caskets/coffins are not used, and the bodies decompose over time, allowing more people to be buried there.

Once you hit Park Street, on the right beings the Boston Commons, with the frog pond (an ice skating rink in the winter), swan boats in the summer, and 50 acres of grass to lounge in. In the winter, look for holiday lights and the Christmas Tree sent from Nova Scotia each year. If you continue far enough, you’ll enter the Public Gardens which are beautiful when flowers are in bloom! Oftentimes there are concerts and events here, so check in advance!

You’ll now be close enough to the Theater District, Chinatown, and Downtown Crossing, which are small neighborhoods where you can choose-your-own-adventure. Usually, city-sponsored information officers line the street at Downtown. NOW IS THE TIME to get your iced Dunkin Donuts coffee like a true Bostonian (regardless of the season)! I also love bubble tea from New Dong Khanh Restaurant, although you’ll see many big Korean chain bubble tea shops as well.

This is the point during the day in which I’d take a break from walking, and take an uber to Downeast Cider House in the old Shipyard of East Boston. Tours require you to sign up ahead of time, but anyone is welcome to walk in for free tastings of the locally made, unfiltered hard ciders! The staff are friendly, and the shipyard itself has an eclectic collection of artwork scattered throughout. In nice weather, the Institute of Contemporary Art has a popup exhibit (The WaterShed Gallery), and a walk to the neighboring Piers Park offers stunning views of Boston across the water.

FOOD: KO Pies is next to Downeast, and they serve Australian pot pies (even for vegetarians). If you’re looking for something that better matches the local vibe, try $1 pupusas at Topacio (a Salvadorian spot, my favorite) or Tu Metapan (my friend’s favorite). It’s a bit of a walk, so I’d recommend Uber or Lyft, especially when it’s cold! There are many local Mexican and Colombian restaurants near Maverick Station as well, if you’re looking to get back on the train afterward. If you want to explore the Italian half of East Boston, look no further than Rino’s Place.

TO DO: In the summer, I recommend taking the train to Revere Beach and looking for Banana Boat, where you can get Richie’s Slush. It’s a uniquely Boston treat that is an indescribable mix between Italian ice and sorbet. The beach itself isn’t the best for relaxing (drive to any more northern beach for that), but it’s more than enough for ice cream, people watching and walking.

FOOD/TO DO: This would be a great time to head back to wherever you’re staying for a short (or long) rest. If you want to experience the limited nightlife Boston has to offer, later in the evening you’ll head back out to the Theater District, perhaps stopping at Genki Ya on Tremont St. for sushi (veg options!!) or any of the nearby bars for a bite or a drink. Most of Boston’s nightlife takes place underground, and the city is an anomaly in that the most popular bars are often hotel bars. Do a little research to see which vibe best matches what you’re looking for. NOTE: Bostonians don’t often go to clubs before 11:00pm, and remember that everything shuts down at 2:00am.



Today will begin in Cambridge, north of the Charles River. The Red Line or the 1 Bus will take you from Boston into Cambridge, and it’s much easier to use public transportation here (or borrow a Blue Bike) than to drive. You’ll find that Cambridge has a distinctly different feel than Boston, and it’s Cambridge, not Boston, is the official home of schools MIT and Harvard.

FOOD: Blackbird Doughnuts has a new shop near Harvard Square, but if you’re looking for a healthier option, Veggie Galaxy in Central Square is an all-time favorite for vegans and carnivores alike. It’s set up like a retro diner and doesn’t offer any meat, but no one seems to notice with their creative replacements and well thought out flavor combos. Clover offers a quicker breakfast has dozens of locations throughout the city (both in Central and Harvard Squares), and it started out as a food truck in Cambridge with locally-grown offerings.

Brunch is big in Boston, so almost everywhere you look on Sunday mornings (and afternoons…) you’ll see brunch options and hungover college kids. Keep in mind that “bottomless” drinks are illegal here, so no sense in searching for that, but whatever type of food you want, you’re likely to find somewhere on Mass Ave in Cambridge.

TO DO: If you ate near Central Square, check out the space next to Central Kitchen (565-567 Massachusetts Ave), known as Modica Way, or Graffiti Alley. This short passage has constantly changing art on the walls, and cool lighting thanks to the stained glass rooftop.

The walk from Central Square to Harvard Square is about 15 min, and both have train stations that are 1 stop apart from each other on the Red Line, so if you’ve started the day in Central, it should be easy to head up toward Harvard. You can’t miss Harvard Yard, the freshman dormitory area for the university students, and most people enjoy walking through the COOP, Harvard’s bookstore across the street. You’ll see that it would be impossible to “pahk ya cah in Hahvahd Yahd” because the area is gated, but pedestrians (no bikes) are welcome to walk through. Ask for directions to the Whispering Arch in Sever Quad, which allows two people to stand on opposite sides of the doorway and whisper to each other, being heard perfectly clear!

After leaving the Yard, take a walk around the block in any direction for a slew of fun stores, gift shops, and other oddities. Black Ink is a quirky kitsch shop, Zinnekins has Belgian waffles you can smell from outside, and Follow the Honey has raw honey on tap. Yoga and meditation studios abound, if you’re up for it, and a community acupuncture clinic lets you really lay into the Cambridge-y vibe.

FOOD: Hop on the Red Line again and we’ll continue heading north, to Davis SquareFor lunch head to Boston Burger Company. They have a massive list of massive burgers, and instagram-worthy milkshakes you usually only see in NYC. The fries are more like potato wedges and the bruschetta fries are a meal by themselves. This may be the last meal you need today!

Alternatively, if you haven’t gotten your seafood fix yet, Legal Seafoods is a popular chain restaurant. Alive and Kicking Lobsters, Row 34, Neptune Oyster, and North Square Oyster are all well-known spots, although not necessarily on our trail this weekend.

TO DO:  Sit and digest in Statue Park (the small area on the corner in front of JP Lick’s) to people watch, and usually you’ll get to hear a busker with a guitar. On the weekends there are often art festivals in this part of town.

When you’re ready, discover Candlepin bowling. It is a New England (and Canadian?) pastime with small pins and balls, and no bumpers. Take a short walk to Sacco’s Bowl Haven (connected to Flatbread Pizza) to try it out!

For the evening, also near Davis Square you’ll find Somerville Theatre, opened in 1914, showing box office hits. However, it’s more fun to go to one of their live shows, like Sh*tfaced Shakespeare or Drunk Disney! Discount tickets are usually available through GuideStar.

Before you leave Boston, try to ride, drive, or walk along the Charles River at night, when the entire city is lit up. The Cambridge side of the river is Memorial Drive, and the Boston side is Storrow Drive. Walking over the Mass Ave bridge, or even taking the red line between Charles/MGH and Park Street will give you an amazing view in both directions.


I’d love to hear what your favorite things are about my favorite city!

Other noteworthy places to check out if you have more time:

Oberon (American Repertory Theater) – always has fun, immersive nighttime events, like the weekly Donkey Show on Saturdays. Between Central and Harvard Squares.

Life Alive – fresh vegetarian food and smoothies on Mass Ave near Central Square.

Boda Borg – this is cool “escape room” for kids and adults alike (I’ve been many times as part of “team building” work activities, and also with friends). Teams of 3-4 people work through mental and physical challenges in 16 challenges with over 30 rooms. Reserve online to ensure a spot. There is parking nearby and it’s a short walk from the Orange Line.

Christian Science Center & Reflecting Pool – A picturesque spot to sit outside during warmer months, near the Prudential Center Mall, Symphony Hall, and various universities.

Museum of Fine Arts (MFA) – What looks like a very traditional museum on the outside is truly comprehensive inside, having something for everybody. They have free admission on Wednesdays after 4pm and kids 7-17 are free on weekdays after 3pm, and all weekends.

The Lawn on D – A temporary outdoor exhibit-turned permanent playground for adults, located in Southie. You’ll find a beer garden, food trucks, live music, and playful art installations during warmer months.

Institute of Contemporary Art (ICA) – not only is the museum cool to visit, but the ICA hosts events almost every weekend in the summer in their waterside outdoor space.

Nearby neighborhoods we missed that you should check out next time:

  • The South End
  • Seaport
  • Somerville
  • Brookline
  • Roxbury
  • Jamaica Plain

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