Naxos was amazing! Very low key, and avoided the crowds of Mikonos (Party Island) and Santorini (newly wed central). Rent a cheap car on Naxos and explore. Stay at Michaella Studios and best food at Paradise Tavern Kastraki.
Indirect advice: If you can swing it, don’t skip Turkey (at least Istanbul) while you’re over there. Best trip we ever took was a couple weeks exploring Turkey.
Skip all the touristy spots and onto Milos. Much more authentic. Half of the island is only available by boat. We did this boat trip and it was really fun
Santorini in mid September is quite good. Not too crowded, good weather, nice beaches and sights. Although one has to get used to tap water being desalinated because no sources of natural water. Personally didn’t enjoy showering e.g. but not that terrible. But any Greek island will be great to visit
Santorini. I read a guidebook that said people tour islands, get to Santorini last and wish they’d spent the whole time there, so I went straight there. Worth it.
Stayed in an incredible place carved into the hillside.
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https://milosoneiro.com
Stayed in an incredible place carved into the hillside.
I did some of the party islands when I was younger- Mykonos, Rhodes, and Ios. I think Ios was my favorite.
I’d imagine it’s hard to go wrong with any of the Greek islands. The only thing we did was avoid Mykonos bc that’s just not our scene.