Check out the breweries while you're in Jamaica Plain. Hop on the metro at Green Street Station and Heath Street Station to see top sights like Arnold Arboretum and The Footlight Club.

Home to Fenway Park and the Museum of Fine Arts, this vibrant area boasts numerous educational institutions, cultural attractions, and independent shops. Easily accessible via MBTA subway and bus lines, explore Kenmore Square and admire the iconic Citgo sign.

South End is noteworthy for its cafes, and you can make a stop at top attractions like Cathedral of the Holy Cross and Copley Place.

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

Consider a visit to John F. Kennedy Presidential Library and Museum and take some time to enjoy the abundant dining options during your time in Dorchester. If you want to see more of the city, jump on the metro at Fields Corner Station or Four Corners/Geneva Ave Station.

While you're in Bay Village, take in top sights like Blue Man Group and jump on the metro at Tufts Medical Center Station to see more of the city.