Where Fashion Meets Life

Planning a trip to Boston? This guide covers the best hotels, restaurants, and things to do based on several of our trips to the city. From Bruins hockey at TD Garden to historic landmarks, cozy cafés, seafood towers, and winter walks through Boston Common, these are the places we return to again and again. Whether you’re planning a romantic destination date or a quick weekend getaway, this Boston itinerary will help you make the most of your visit.

A last-minute idea turned into the perfect quick escape — a destination date to New Orleans to see Wicked with friends. From smash burgers in Ponchatoula to a boutique stay on Canal Street, a delicious dinner, and a magical night at the Saenger Theatre, this overnight trip proved you don’t need a long vacation to make meaningful memories. Good food, great company, Broadway magic, and just enough adventure to make us want to plan the next getaway.

Boston has become one of our favorite Destination Date cities — full of history, incredible food, and endless walking. From cozy historic hotels and unforgettable Italian meals to cannoli debates, the Freedom Trail, hockey at TD Garden, and late-night pastry runs, this guide rounds up our favorite places to stay, eat, and explore. If you’re planning a romantic weekend (or just love a good city itinerary), Boston delivers every time.