With 20 main islands in the 220-island chain, you can still try somewhere new, though. Fly to Santorini, where you can begin your trip on an old favorite. Then ride the Flying Cat III to the small island of Folegandros—you’ve probably never even heard of the 12-square-mile island, much less visited it. It’s only a 45-minute ride, but the ferries rarely arrive or depart on time. Folegandros doesn’t have an airport though, so the sea is your only option.
You’ll dock at Karavostasis, the small port that awakens when the ferry arrives. It has a few cafés, small shops, and one road out of town. As you head north on the bus, you’ll climb a rocky hill full of cacti. A couple of small white houses, olive groves, goats, and not much else are in the distance. It’s unlike any of the welcoming Greek islands you’ve visited before.

The bus drops you off in Pounta, a square on the outskirts of Chora, the island’s capital. No cars are allowed inside Chora, and once you start walking through the small village, you’ll understand why. Chora is built within the walls of a 13th-century Venetian castle. The narrow streets, which are lined with steep staircases that lead to small white houses, open up to squares filled with open-air tavernas, crumbling churches, and fragrant bougainvillea. The Church of Panagia sits on the hillside overlooking the village, and 200-meter cliffs drop off the other side. Widows walk around Chora in black, well-fed cats are everywhere, and the few tourists you pass are probably French. Everyone smiles and says “yassas” when you walk by.
You’re staying at the cliffside Aria Boutique Hotel. Your simply decorated room has a wrought-iron bed, a jacuzzi tub, and a high-beamed ceiling. You open the doors to your balcony, grab the welcome bottle of wine, and enjoy the view of the pool, the Aegean Sea, and Panagia. It’s quiet and stunningly beautiful.
Later, you’ll check out the other town squares: Lili Bechraki, Ntounavi, Kontarini, and Piatsa. Peek in the windows of Agia Eleoussa, Agia Sofia, Agios Antonios, and Agia Aikaterini. The churches are locked except for the feast day for the saint to whom they are dedicated. Drink strong coffee or a Mythos beer and play backgammon for hours at a café. Take the bus to the island’s other village, Ano Meria, to visit the Ecological & Folklore Museum and Agali, Folegandros’ best beach. Eat tzatziki, pastitsio, moussaka, horiatiki salata, kebabs, and sardines in Pounda’s walled garden. Climb the switchback hill to Panagia to watch the sun set. It rivals Santorini’s—minus the crowds—as the best sunset in the Cyclades. And drink warm rakomelo with honey at Baraki while listening to acoustic guitar music at the end of the evening. You’ll be grateful there are no cars when you stumble back to Aria.
Folegandros may not immediately welcome you the way Milos does; its natural beauty isn’t immediately apparent like Santorini’s; it doesn’t cater to tourists the way Mykonos does. The little island is unapologetically set in its Greek ways. People either love it or hate it. And you absolutely fell in love. It’s now another reason you’ll continue to return to the Cyclades.
Great shot!