1 Best Bar in Boston, Massachusetts

The Anchor Boston

Nestled just 20 feet from the oceanfront, The Anchor is an open-air public gathering space, performing arts venue, and wine and beer garden. The two-story venue is full of swings, huge pillows set against stone terraces, lounge sets, and a grassy lawn for relaxing and sipping your cocktail. The menu offers items like air-fried cheese curds, jalapeno poppers, tacos, nachos, and chowder. The amphitheater hosts live music or movies seven nights a week, while other free events include comedy nights on Sunday, Monday salsa classes, waterfront wellness classes every day (think yoga, boot camp, Zumba), and live paint nights every Tuesday. In wintertime a dozen heated igloos and several fire pits keep things cozy.