Over the past few years, I’ve somehow become a frequent Boston flyer. I usually find myself there at least three times a year for work, and somewhere along the way, it stopped feeling like just another business trip and started feeling like a city I genuinely love.
I definitely wouldn’t call myself a local, but I think I’ve earned the right to have a few opinions.
And here’s one of them: when I first learned Boston’s nickname was “Beantown,” I hated it. With “The Bean” in Chicago being so iconic, it just felt confusing. But then I learned the nickname actually dates back to Boston’s history and its famous colonial baked beans. At that point, I had no choice but to respect it. It’s still not my favorite nickname for a city, but at least now I understand it.
Navigating Boston
Boston, as a city, is surprisingly easy. Logan Airport is one of my favorites because it’s manageable, there are plenty of flight options, and you’re usually at your hotel before you’ve even had time to call your mom and tell her you landed safely. It’s one of the few major cities where I don’t brace myself for an hour long Uber ride. And the lounge situation doesn’t hurt either. If I have time before flying home, I’m usually at the Chase Sapphire Reserve Lounge, even if it still doesn’t beat LaGuardia. (Sorry, Beantown.)
I’ve also learned there are definitely better times to visit. May and June are hard to beat. Everything turns green, everyone’s outside, and the whole city feels lighter. October and November are on another level entirely. If you want peak New England fall, Boston absolutely delivers with all the red, orange, and yellow leaves.
Quick tip: check the calendar before booking in April. Marathon Monday takes over the city, and unless you’re going for the race, getting around can be more chaotic than expected.
Coffee Guide
One thing I didn’t expect when I first started coming here was my obsession with Tatte (like latte).
Yes, Boston runs on Dunkin', and honestly I get it. If I need coffee quickly, I'm grabbing DD every time over Starbucks. It just feels wrong not to thanks to Ben Affleck. But Tatte is my place.
Tatte's coffee is amazing, but I could go just for breakfast. The pastries are Pinterest-worthy, and their breakfast menu goes above and beyond what you expect at a cafe. Scrambled egg plates, shakshuka, croque madame... it's way beyond your typical coffee shop. Every time I'm in Boston, I end up there at least once, usually more. I wonder if Ben Affleck knows about Tatte.
Back Bay Boston
I almost always stay in Back Bay, mostly because I think it's the perfect home base. Everything is walkable, there are tons of restaurants, shopping, and if Boston decides to rain or freeze, you can spend hours inside the Prudential Center without getting bored. It's basically its own little utopian, capitalist ecosystem.
One of my favorite rituals has become running along the Charles River, especially at sunset. It’s one of those moments that reminds you why people love living there. Another great route is Commonwealth Avenue. Between the brownstones and tree-lined streets, it’s the kind of place where you accidentally slow down just to take it all in.
I also never get tired of walking Newbury Street. Sometimes I’m shopping, but most of the time I’m just window shopping thanks to my fully developed frontal cortex that no longer allows me to be financially irresponsible.
One place I keep going back to is The Newbury Hotel. I've actually never stayed there, but I've run up tabs that would rival a nightly rate. The Street Bar is one of my favorite hotel bars anywhere. It's cozy and elevated with rich fabrics and furniture, and the perfect spot for a breakfast meeting or afternoon drinks. On this last trip, I finally made it upstairs to Contessa for brunch, and the view over the Public Garden was even better than the French toast.
Then there's Beacon Hill and all of its charm. Every street looks like a movie set with the brick sidewalks, gas lamps, and flower boxes. I wandered into Beacon Hill Books & Café and was instantly inspired by its quiet charm and quaint atmosphere. It's one of those places that immediately feels cozy the second you walk in.
The Crown Jewel of Beantown
I've also made the obligatory visits to Boston College and Harvard. Boston College is gorgeous, and while I'll always be loyal to SMU, I can absolutely appreciate a beautiful campus. Harvard was fun too, but I think I actually enjoyed Harvard Square more than the campus itself. It just has this constant energy that makes you want to stick around a little longer.
But honestly, my favorite thing about Boston isn't any of those places.
It's the people, as cheesy as that sounds. Growing up in Mississippi and spending most of my life in the South, I was used to one kind of hospitality. Boston has a completely different version.
People are direct. They don't spend much time pretending or tip-toeing around topics. At first, I wasn't sure what to make of that.
It almost feels like there's an unspoken trial period. Once you make it through that, you've got a friend who's incredibly loyal, protective, and genuine. They're still going to tell you exactly what they think, but somehow that's part of the charm.
Every time I leave Boston, I find myself adding another restaurant to my list, another neighborhood I want to spend more time in, or another excuse to come back.
