"It’s unclear whether the menu at the Beacon Hill Hotel Restaurant has been updated since 2010, but you're not here for innovation. You're here for well-executed comfort food, like super savory wagyu bolognese over fresh pappardelle (a favorite with the regulars) or a juicy burger on brioche. The sunny dining room is a fine place to grab a crisp Caesar salad lunch (snag a seat facing the cobblestone streets for prime people watching) but in the evening, the bar is the spot to be, where a mix of cashmere-draped locals and tourists nurse cocktails from cut glass barware. Try the Kentucky Derby, with bourbon, Aperol, grapefruit, and maple syrup. If the weather is nice, grab a seat on the rooftop terrace bar, where you can sip Holmes Herbal Remedy, an elderflower-spiked gin and tonic that pairs perfectly with a burrata and Iberico ham plate." - Catherine Smart