The Azor islands

Nine stunning and distinct islands make up the Azores,  an archipelago in the Atlantic Ocean, an autonomous region of Portugal, which is sometimes known as the Hawaii of the mid-Atlantic. Each of these islands has its own culture, charm and unique scenery including volcanic landscapes, green pastures and crater lakes. And much more. If you have never visited, you must check it by yourself.

The most isolated are in extreme Western (Corvo and Flores) and in the extreme Eastern (Santa Maria). The most populous and best served by plane connections are São Miguel and Terceira Islands. I think that all the islands have plane connections and most of them have also regular boat connections.

São Miguel or Terceira would be the most livability for you. But from these islands you can visit the others and enjoy what each one has to offer.

You can also see some Youtube Channels spoken in english made by other expats in Portugal, also in Azores islands. At "Stay Classy Vlog"  channel, please select video playlist youtube option and watch some of the Azores vlogs made by this danish couple who lives in Portugal.

I hope this will help your choice.