1. Try: Naxos and Milos, Greece. Not: Santorini.
There’s no denying the beauty of the Cyclades, especially the iconic Santorini sunsets on Oia, but there’s only so many times we can see that same scenic view on Instagram before it gets played out.
If you’re looking for a taste of off-the-beaten path Greek culture, stay on the Helenic Seaways ferries for a few more stops, and hit nearby Naxos and Milos. On Naxos you’ll find opportunities to experience old-world Greek charm in villages like Chalki, or fresh seafood in fishing villages like Apieranthos, as well as hiking and cycling trails. On Milos you can sail to unspoiled beaches like old pirate caves at Kleftiko, and stroll among the technicolored doorways of the fishing port of Klima. And did we mention the local specialty is watermelon pie? Sold.