Our neighborhood-by-neighborhood guide to ideas for romantic excursions out on the town
A vibrant, yet intimate, neighborhood, Boston’s North End is a bastion of Italian cuisine and culture, as well as the oldest residential area of the city. The cobblestones of North Square are intersected by the famed Freedom Trail, so walking through history with your loved one is always possible. Closer to the waterfront, the trellis archways of Christopher Columbus Park (pictured)—which have been transformed with blue lights and heart-shaped decorations to form a "Tunnel of Love" through February 21—have allegedly been the site of many marriage proposals. Dining is imperative here, however, so head to romantic mainstays like Massimino’s Cucina Italiano and Terramia Ristorante, two of the area’s many cozy eateries. If you’re the type that associates oysters with Valentine’s Day (and you know who you are), then seafood stalwarts like Neptune Oyster and Mare are safe bets for crustacean indulgence.