Things To DoThings To Do

Sean & Winta's RecommendationsSean & Winta's Recommendations

Walk the Freedom Trail Get cannoli in the North End Watch sunset along Boston Harbor Visit Fenway Park Take a Swan Boat ride Explore Beacon Hill Try a lobster roll while you're here Spend a day on Martha's Vineyard (if you're in town early - Martha's Vineyard African American Film Festival (MVAAFF) One of the country's premier celebrations of Black film, culture, and storytelling. Held on Martha's Vineyard from August 7–15, 2026. Must-See Boston • Freedom Trail • Boston Common & Public Garden • Fenway Park • Boston Harbor & Harborwalk • New England Aquarium • Museum of Fine Arts • Isabella Stewart Gardner Museum • Boston Public Library Neighborhoods Worth Exploring North End: Boston's Little Italy. Cannoli, espresso, and cobblestone streets. Beacon Hill: Historic brownstones and gas-lit streets. Back Bay: Shopping, restaurants, and iconic architecture. Seaport District: Modern waterfront dining and nightlife. Cambridge: Visit Harvard Square and stroll along the Charles River.