Island Hopping in Greece: The Perfect 2-Week Itinerary

Greece has over 6,000 islands, but only about 200 are inhabited. Choosing which ones to visit is the hardest part of planning a Greek island trip — so I've done it for you, based on three separate island-hopping adventures.

Start in Athens with one night to recover from your flight and visit the Acropolis at sunset. Then catch a morning ferry to Milos — the island that's been quietly stealing Santorini's thunder. Saganaki Beach has cliffs that look like they were sculpted by Gaudí, and Kleftiko's sea caves are best explored by boat.

From Milos, take the ferry to Santorini. Yes, it's touristy, but for good reason. Stay in Oia for the famous caldera views, but explore the less-visited south coast — Red Beach and Vlychada's lunar landscape are worth the drive. Skip the overpriced seafood in Ammoudi Bay and eat at a taverna in Pyrgos instead.

Next, hop to Naxos — the largest of the Cyclades and the most underrated. It has the best beaches in the Aegean (Plaka and Mikri Vigla), a charming old town with a Venetian castle, and mountain villages where time moves at a different pace. Rent a quad bike and explore the interior.

End your trip on Paros or its tiny sister island Antiparos. Paros has the perfect mix of nightlife (Naoussa), culture (Parikia's old town), and beaches (Golden Beach for windsurfing). Antiparos is where you go to do absolutely nothing — and feel great about it.

Ferry booking tip: use Ferryhopper to compare schedules and prices. Book popular routes (Athens-Santorini, Santorini-Mykonos) at least a week in advance during July-August. For island-to-island routes, you can usually book a day or two ahead. High-speed ferries cost more but cut travel time in half.