My wife and I vacationed in Portugal a few years back. We stayed in Cascais before heading to Lisbon (both were stunning and the people extremely friendly - Cascais was like a mini-Lisbon on the sea to me). In any event, we took a little sunset sailboat ride and the young gentleman at the helm said he was from the Azores. He said it can be quite remote, but he thought it was one of the most magical places he'd seen and implored us to visit. It's #1 on our list as well.

Also, I have half a mind to visit Paratay, Brazil. All I know is the song Paratay by Mia Doi Todd (1), but as I listen to the lyrics, that's enough to get my wanderlust stirring.

1. https://youtu.be/QID5HNlSMjw

You could island hop across the Atlantic. Bermuda -> Azores -> Canaries. Work your way up the Irish sea from the Scilly Isles -> Lundy -> Skomer -> Bardsey -> Angelsey. On up to Faroes (Bonus points for a stop off on Rockall) -> Iceland -> Svalbard.

That would make an nice amateur radio Islands On the Air (IOTA) expedition.

Azores is brilliant and only a four hour flight from Boston / east coast. Highly recommended, especially if you like backpacking, or day hikes.