Sitting atop the island of Terceira, Praia da Vitória dates back to the original settling of the island, one of two founding ports. While it’s not the 1400s anymore, the city’s historic core still sports cobblestone streets lined with churches and unique local shrines called “imperiós.” Elsewhere on the island is Angra do Heroísmo — that’s Terceira’s other founding port — which was briefly the capital of Portugal and today is an area you should explore! Angra do Heroísmo is a UNESCO World Heritage Site, and its cityscape of clay-tiled-roof atop 16th-century buildings gives it a familiar Mediterranean charm. Outside of the constructed world, check out Algar do Carvão, both a cave and an underground lake formed by a volcanic lava tube.