A Weekend in Boston
What’s up with the Citgo sign?
If you’re not from Boston or a neighboring town in Massachusetts, it may seem odd that an extraordinary amount of Bostonian pride is represented by an oversized gas station sign hovering over an ancient ballpark (Go Sox). But, it only takes a couple of days spent in town to realize that it’s what lives under and around that sign that makes the historic city so wonderful. I recently hosted a friend from New York for the weekend and (after deciding to go against our every instinct to spend the weekend on the couch, ordering Indian food and watching Love Island UK) I rediscovered all of those wonderful things as if for the first time. It inspired me: to do it more often and to force it upon others!
Here’s how to spend a long weekend in Boston experiencing it all:
The South End
The South End is great for our trendy, social, but low key 30-something girlies. There are chic restaurants, moody speakeasies, and cool coffee shops situated between beautiful brownstone-lined streets reminiscent of the most instagrammable New York neighborhoods.
Start your weekend here (and start it on Friday night, we’ve got a lot of ground to cover over the next two days!). There are plenty of dining options on Tremont Street, also referred to as “restaurant row.” Consider eating dinner at Black Lamb, Coppa Enoteca, or split some tapas at Toro. Then, walk over to Wink & Nod for a night cap. It’s a modern and sexy speakeasy, illuminated by chandeliers and a backlit bar. Don’t be intimidated - you don’t need to knock on any hidden doors or recite a password to get in.
If you’re exploring the South End during the day, check out the artsy couple of blocks referred to as SoWa (“South of Washington”). Pop into an art gallery, grab a taco or two at a food truck, and stroll through the open-air market. As their website will tell you, it’s a particularly vibrant community from May through October. You can catch their holiday market starting in November!
Beacon Hill
Start your Saturday by grabbing a coffee at the Tatte on Charles Street. You can skip the Dunkins run, tbh. Grab your caffeine and a croissant and head across the street to the most charming bookstore in the world, Beacon Hill Books. There’s an adorable cafe on the garden level. If you need another coffee, or if tea is more your speed (you are in Boston after all…), venture through the stone archway which is accessible from the street, and walk through the narrow stone tunnel (it’s whimsical!) to the cafe. Grab a table inside or outside and thumb through the books you just purchased.
Ok, it’s time to channel your inner-influencer. Head up Mt. Vernon Street and take a right on Willow Street to find one of the most famously photographed cobblestone alleys, Acorn Street. Weave your way in and out of this hillside neighborhood. There are plenty of homes you’ll want to search on Zillow later.
Walk across Beacon Street and through the Boston Public Garden to the Newbury Hotel. On the rooftop, you’ll find Contessa, a new and trendy Italian restaurant that somehow feels like you’re in Miami (maybe because they also have a location in Miami). The Ricotta Gnudi Di Pecora is amazing, the veal is delicious. Do not, under any circumstances, skip dessert. I’d recommend making reservations ahead of time - it’s a popular place!
Less than a mile away from the Newbury Hotel is the esplanade, a historic park that runs along the Charles River (of dirty water fame). Walk off your 4-course lunch on the esplanade by crossing any of the footbridges that connect the Back Bay neighborhood to the long stretch of riverfront pathway.
After your jaunt along the river, sit by the duck pond or underneath one of the centuries-old trees at the Public Garden. In the spring and summer, you could snag a seat on a Swan Boat and go for a spin around the pond. You’ll want to rest up for dinner at Mariel, a new Cuban restaurant in the Financial District. After a couple of mojitos, ask about how to get into their club, The Underground, if you feel like dancing. Or, opt for a short walk to Faneuil Hall. Some may try to tell you that the bars on this block are for tourists but any good millennial from the greater Boston area spent the better part of their early 20s frequenting Ned Devine’s. You may also find some live Irish music and a pint at the Black Rose.
The Seaport
The Seaport is the newest neighborhood in Boston. Most long-time Massachusetts residents still marvel at the fact that this area of South Boston was solely industrial until about five or six years ago. Now, the waterfront is home to shops, restaurants, hotels, and seasonal activities.
Arrive mid-morning for a caffeine fix and shop the day away. In all honesty, some of these stores can be found anywhere (similar to the way Hudson Yards in NYC feels exciting until you realize it’s just another mall). But, many shops are unique with a primarily e-commerce presence. Need a new Away carry-on for the trip home? You’re in the right place!
At some point you should wander over to the harbor for yet another influencer moment. The views from the pier near the Institute of Contemporary Art are quintessential Boston. If the weather is nice, grab a beer at the outdoor brewery or head to the rooftop bar at the Envoy Hotel and say one last final Cheers (Does Gen Z know who Ted Danson is?) to Boston.
Ending your trip in the Seaport is the perfect way to experience your weekends’ last moments in town. It honors the old and the new, the historic and the modern: sleek new buildings run adjacent to cobblestone streets; trendy cocktail lounges overlook the historic harbor. The only negative? The parking rates are outrageous. But, it's a good reminder that the weekend is over and you gotta get back to work tomorrow.
