I get a lot of emails from people asking what island would fit them best. Here is my take on this.
If you like a place which has plenty of people and services then you might want to head for Sâo Miguel Island or Terceira. Terceira, because of the decades of US presence at Lajes Airforce base, is somewhat Americanized when it comes to peoples ability to Speak English and availability of your favorite snack food. With the gradual withdrawal of US troops the economy obviously has taken a hit. How this pans out for the future we do not know yet.
Sâo Miguel is the most populous but outside Lagoa and Ponta Delgada there is enough space to live. Expect parking to be an issue in town.
Santa Maria is the sunniest of the Islands Islands. Sparsely populated but close enought o São Miguel for proper logistics it offers peace and quiet. Houses are few so expect somewhat higher prices for properties similar to other islands.
The Central Group with Faial as the seat of the Azorean Government has the benefit of 3 islands that are well connected with ferry services. The beauty of the Azores is that the islands are very different. The Central Group offers weekend getaways on other islands and stunning views of Mount Pico. We chose Faial because of the University and a proper equipped hospital (just in case…) . It is also less densely populated so expect more quiet places. The Marina of Horta receives over a 1000 yachts a year. From small sailing boats to mega yachts. It is a must do stopover for those crossing the Atlantic and has been so for centuries. Because of that the city and its inhabitants are more cosmopolitan than one might expect of such a remote place. São Jorge is a bit more remote as the ferry takes over 2 hours from Horta and an hour from Pico. If the weather is bad…you can forget about boarding the ferry. Pico offers nice landscapes, plenty of houses and is only 20 minutes by ferry from Faial. It lacks a proper hospital. For years it is being discussed but with a population of 16,000 it is hard to justify a fully equipped hospital. Faial services the Central Group.
Graciosa, Flores and Corvo. This is pretty much away from the beaten track. Not always easy to reach. Logistics is a project but if you want to really be away from it all these are the most remote of destinations you will find. A community of a few hundred like on Corvo might not be the easiest to blend into.