Reside among locals at the Hotel do Colégio (from $132), a 55-room former music academy set amid Ponta Delgada’s cobblestone streets and elaborate churches. Browse the hotel’s gourmet shop for local honeys and Azorean teas from Goreanna ($3-8), Europe’s only tea plantation.
Overlook the ocean from the flower-covered Caloura Hotel (from $128), an 80-room resort nestled above a private rocky beach that’s also home to a dive center, gym, sauna, and tennis courts. Forgo the overpriced in-house restaurant in favor of the second-floor bar, where you can watch the sun set over the water.
Admire panoramic views of Pico Mountain from a second-floor room at Baía da Barca (from $128) in Pico. A series of volcanic trails begins a few yards from the property, and the windswept Atlantic Ocean is less than 50 yards away. Still, don’t miss the luxurious pool and Jacuzzi, where locally brewed Especial is the drink of choice.