A Weekend In Boston

48 hours in Beantown is ample time to fall in love with Massachusetts’ capital city

It’s rare that Seth and I get to go somewhere when it’s just the two of us and we have no agenda. Our Boston weekend was a treat for that reason alone, in addition to the fact that we made our base right in the heart of the thriving northeastern hub at the Fairmont Copley Plaza.

And while we had just shy of 48 hours in Beantown, we know how to make the most of any city escape, no matter how short it may be.

It’s a quick and easy flight from Nashville to Boston; we flew out of BNA just after breakfast and touched down in BOS at lunchtime. When we arrived at the Fairmont, our room was all ready to go early so we dropped our bags and freshened up before hitting the pavement.


In truth, I was exhausted from hosting visiting friends in Tennessee all week and wanted nothing more to nap, but the city was calling our name and we didn’t want to sleep our way through such a gorgeous spring day.

One thing I miss from living up north is the abundance of grab-and-go options that are both healthy and affordable. I’m talking, hearty salads, faro bowls, wraps, the like. Nashville simply doesn’t have many fast-casual options, let along healthy ones, so Seth and I try to get our fill when we travel to big cities like Boston—which is why our first meal was not lobster rolls but rather a quinoa concoction from Dig Inn that left us satisfied and ready to get going.

After that, we couldn’t think of a better way to soak up the sunshine that in Boston Common. Everyone else in town seems to have the same idea. Boston on a sunny day seems a throwback to our days living in Denmark; the second the clouds dissipate and the mercury creeps above 60 degrees, every green space in town is occupied by sun-deprived bodies, the heat drawing them out their frozen indoor solitary confinement.

View of the Charles River and the skyline of the Back Bay from the parking garage at the Museum of Science in Boston, Massachusetts.

We shopped our way through Back Bay on the walk home to the Fairmont, returned to our rooms to clean up, then headed downstairs for dinner at OAK Long Bar & Kitchen. Everything on the dinner menu looked so tantalizingly good that Seth and I decided to forgo the entrées and instead share a respectable selection of the small plates, as well as a couple of cocktails starting with the Kentucky Elixir.

Merguez lamb meatballs with tomato sauce, gremolata, onion crostini; roasted cauliflower with golden raisins, mint, sherry and almonds; and, of course, mac and cheese with confit pork shoulder, Béchamel cheese blend—we sampled a little bit of everything.

The meal was mind-blowingly delicious, made only tastier by the fact that we were served Chakib from Casablanca, who was impressed we’d visited his hometown and steered us through the menu, course by course. After he’s evaluated our cocktail tastes, he was so bold as to suggest new drinks and even have the bartender whip us up something special (good man, that Chakib). We rolled ourselves back up to the fourth floor and vowed never to eat again, a promised we kept for a solid 12 hours until it was time for brunch.


Although I’ve been to all 50 states and well over 120 countries, I’m still one of those travelers who likes to hit all the tourist hotspots and I’ve yet to spend a weekend in Boston and not walk at least part of the Freedom Trail. Since we had so much walking on the docket for the day, we filled up on a hearty breakfast from OAK because full as I may have been from the previous night, I’m never one to say no to brioche French toast with Irish cream vanilla custard (and if I do then you’ll know the apocalypse is upon us and a zombie has actually overtaken my body.)

On our way out to hit the Freedom Trail, we stopped to get a map with a side of advice from Joe the concierge. The 2.5-mile red brick trail leads from Boston Common to Bunker Hill, and we didn’t necessarily need to go to them all again, so we asked him for his greatest hits list, which he gave us in addition to some of the best photos stops in Boston.

Copley Plaza is just 10 minutes from the Freedom Trail’s starting point, so we returned to the park and headed east from there, hitting up a handful of the 16 stops like the Massachusetts State House and the Old South Meeting House in addition to Joe’s recommendations before eventually arriving at Faneuil Hall, which was built in 1741 and hosted America’s first ever town meeting.


Comprising Quincy Market, North Market and South Market, Faneuil Hall Marketplace today is one of the liveliest spots in all of Boston. We ogled the buskers (including one literal pig), inhaled the scent of seafood wafting through the halls, poked through vendors’ stalls and admired the architecture, then continued on our way. When we go down to the waterfront, we found a grassy knoll and finally stopped for a breather.

Our stomachs were rumbling, so I turned to my trusty on-the-go concierge—the Yelp app, that is— and sought out a lunch spot. The result was State Street Provisions, which lived up to the reviews, and we split a burger and seared tuna sandwich and guzzled down a couple of locally-made brews. We did not, however, make it to a brewery in Boston; that had been on the initial docket until, that is, we found that Sam Adams and several other Massachusetts breweries were actually located in suburbs on the outskirts of town (i.e. too far away given our limited time) rather than in Boston proper.

But we had to pick and choose carefully on this trip, and we both wanted to make it over to Cambridge, which is in the opposite directions, so a visit to the Southie did not happen. Next time we’re in town, however, I plan to make the breweries Harpoon and Trillium top priority. Instead, we hopped in the metro and took the train 10 minutes under the Charles River and over to Harvard  Square, which is brimming with shops, cafés, bars and restaurants.


Like Boston Common, the campus was alive with undergrads who seemed to be seeing the sun for the first time after months of hibernation. It’s what my Nashville friends lovingly call National Sundress Day: the first afternoon worthy of shedding those layers of winter clothing and pallor that accompanies a season of being cooped up indoors.

We had no agenda other than more meandering, so when we saw a happy hour at the Red House boasting USD 1 oysters, that became the next sop on our afternoon itinerary. Being in a seafooddeprived state like Tennessee, we get our shellfish fix when we can! I had solicited Boston restaurant recommendations from social media and had a list a half-mile long, but in the end, rather than brave the Saturday night dinner crowd outside of the hotel, we decided to go with a reliable source: OAK Long Kitchen & Bar for a third meal. After all, when you find a good thing, why risk going anywhere that doesn’t measure up? It’s uncommon that I find a hotel restaurant this good, that inventive.

Rush hour was approaching, so we hopped in a Lyft and high-tailed it back to the hotel after we were done with our Harvard Square exploration. We arrived at the Fairmont just before the happy hour crowd, sidled up to the bar as the sun set the room on fire and made friends with John the bartender. Pro tip: Always befriend the bartender.


“What are you having?” he asked with a twinkly in his eye.

“Whatever’s most dramatic—give me your photogenic drink,” was my response.

Rather than do a double take, John paused to ponder my request then immediately wen to town whipping up four of the prettiest cocktails I’ve ever seen, not to mention the tastiest. The winner was, no doubt, the Smoked Chai Manhattan, which John prepared by charring a piece of oak with a blow torch, captured its essence in a snifter glass, then served the drink up to me in a wish of smoke. Magical? I’d say so. John is pretty much the Harry Potter of bartenders, and the Smoked Chai Manhattan ranks among my top five favorite drinks of all time, no lie. Two cocktails in each, we were hungry and the restaurant was starting to fill up. Rather than waiting for a table, we retreated to our room, cracked up a bottle of wine and ordered in-room dining, which is a limited menu curated from OAK. It seemed like the perfect way to unwind after a long day of walking and an early morning looming in the horizon the following day.


Our next destination was my old home, New York City, for a couple of days, and our trip there couldn’t have been more convenient. We got up early, grabbed a light but filling breakfast, checked out of the hotel then wheeled our bags one block over to the Back Bay Amtrak station. Three hours later, we were stepping off the train in the heart of Manhattan, ready for the next leg of our adventure.

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