Angra do Heroísmo, the first capital of the Azores, is the archipelago’s oldest city. This historic settlement, which dates back to 1450, is filled with beautiful colonial-era Portuguese architecture such as the Cathedral of Angra do Heroísmo and was one of the earliest UNESCO World Heritage sites to be so designated. Other highlights include the lush Duke of Terceira Garden; the 400-year-old São João Baptista fort, just south of the city on a promontory at the foot of the volcanic Monte Brasil; and, for an impressively comprehensive look at the city’s history, the Museum of Angra do Heroísmo, housed in a 17th-century convent.