"Let’s start big picture. What’s the vibe here? Beacon Hill's main thoroughfare is a microcosm of all the things people love about Boston: historic architecture, even more historic brick sidewalks, interesting shopping, great restaurants, and unparalleled people watching. On a weekend, especially during nice weather, these cramped sidewalks can get painfully bottlenecked, but on a quiet weekday morning as Bostonians commute to work, there's hardly a more pleasant street in the city. Any standout features or must-sees? While it only takes six minutes to walk end to end, Charles Street is filled with sights and stops that could take hours to properly work your way through. Charles Street begins at the Whitney, a boutique hotel which opened in 2019, and terminates at the Boston Common on Beacon Street. In that third of a mile, you'll find some of the city's most beloved cafés and boutiques, as well as historic monuments like the Charles Street Meeting House, a church and important landmark of Boston's Black community Was it easy to get around? It's quite literally impossible to get lost here since Charles Street serves as one of the only end-to-end arteries for traffic in Beacon Hill. If you decide to peruse the neighborhood's back streets to gawk at some of the best-preserved historic brick townhomes in the country, it's easy to get turned around on the small, one-way, confusing streets. Find your way back to Charles and you'll get your bearings back in no time. There are a few benches and places to sit, and several of the cafés here have restrooms. All said and done, what—and who—is this best for? On a beautiful day, there's nowhere better in Boston to wander aimlessly, linger over a coffee, and watch the locals go about their daily lives. Charles Street can be "done" in about ten minutes flat, but it's also the kind of place you can spend an entire day if you take your time" - Todd Plummer
