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From the colorful and unique imperió shrines that dot the cobblestoned streets of the port town of Praia Da Vitória, to the atmospheric allure of Algar do Carvão, a 90-meter-deep volcanic chimney that formed some 3,200 years ago, the island of Terceira is an utter joy to explore. Spend a day relaxing on a volcanic beach, dive the island’s incredible shipwrecks and reefs, or head to the historic town of Angra do Heroísmo.

With its elegant architecture, cobblestoned streets and restaurant-lined marina, Ponta Delgada on the island of São Miguel is the charming capital of the Azores. See the three-arched Ponta Delgada, which dates back to 1783; sample local cheeses in the Mercado da Graça; or stop to smell the flowers in Antonio Borges Garden. Venture outside the city and you’ll never forget the view from the Mirador do Rei lookout.

Sailing into the famous marina of Horta on the island on Faial is the quintessential yachting experience. This maritime town has been a mid-Atlantic steppingstone for sailors since the Age of Discovery, and today it’s a pitstop for international regattas like Les Sables-Les Açores-Les Sables. Check out the colorful wall on the marina’s breakwater – seafaring superstition states that sailors should paint a message on it to ensure divine protection for their crossing. Take a whale-watching trip or go hiking at Caldeira, a two-kilometer-wide and 400-meter-deep volcanic cone.

Known as the ‘Pearl of the Atlantic’, the volcanic island of Madeira is bursting with exotic colors. The capital city of Funchal is a place to lose yourself in old alleyways, street cafés and pretty squares. See Gothic and Romanesque styles blend at Funchal Cathedral; explore the Contemporary Art Museum, which is housed in the mighty 17th century São Tiago Fortress; or join the locals in the Mercado dos Lavradores, which is adorned with beautiful hand-painted tiles. In the evening, check out the funky Zona Velha.