Ponta Delgada is your introduction to the islands. The archipelago’s de facto capital is on the south coast of São Miguel Island. The Green Island is the largest and most populous of the nine islands. It was also the first of the then-uninhabited islands to be settled, back in 1427, by the Portuguese. So it’s a good place to get your bearings—and a bit of a history lesson.
The Thin Cape began as a small farming and fishing community. In 1522, when an earthquake and subsequent landslide devastated the original capital of Vila Franca do Campo, Ponta Delgada started rising in importance. As the islands’ economy continued to grow so did the city. By the 1970s, it became the capital of the autonomous region that lies nearly a 1,000 miles west of Lisbon.

Given the islands’ remote location, in the middle of the Atlantic Ocean, it isn’t surprising that life in Ponta Delgada revolves around the water. The port is where cruise ships reposition themselves when switching routes between Europe and the Western Hemisphere. The yacht-filled marina does the same for much smaller vessels. Black basalt streets, whitewashed buildings, and red roofs spread out from there. They’re surrounded by the three-arched Town Gates, a trapezoidal City Hall, a maritime fortress, historic churches and convents, and gorgeous gardens.
So there’s a lot to see. You should settle in and get to know the main city before you venture to other islands. Luckily, there’s a new—make that completely renovated—hotel just steps from the marina. The Grand Hotel Açores Atlântico reopened last fall. With mid-century modern furniture, jewel tones, and maritime decor, it does indeed feel like a grand European hotel. An indoor pool is heated for windy mornings. Vapore Bar has an outdoor terrace to sip Verdelho wine in the afternoons. Balcony, the trendy restaurant, showcases fresh seafood. While the rooms have views of the seemingly endless ocean. You have quite an adventure ahead of you.