May, June, September, and early October are the sweet spot. The sea is warm enough for swimming, the archaeological sites are comfortable to explore, and the islands are busy without being overwhelmed. July and August bring the most crowds and the highest prices, and temperatures in Athens often climb past 95°F. The strong meltemi wind also blows through the Cyclades in high summer and can disrupt ferries. Many island hotels close from November to April, but Athens, the Peloponnese, and Crete work well year-round.

Each island has a different character, so it helps to match them to what you want from the trip. Santorini is about caldera views and sunsets, while Mykonos offers beaches, design hotels, and a livelier scene. Naxos and Paros combine sandy beaches with traditional villages and good food. Milos is best explored by boat, with sea caves and a coastline of white volcanic rock. Crete is large enough to be a destination of its own and deserves at least four nights. For a 10 to 12 day trip, two or three islands is usually the right number.

High-speed ferries and catamarans connect Athens’ ports of Piraeus and Rafina with the Cyclades, and also link the islands to one another. The trip from Athens to Santorini takes about five hours by fast ferry. Short flights of under an hour reach Santorini, Mykonos, Milos, and Crete from Athens. For more flexibility, we can arrange private boat transfers or helicopter tranfers.

The site uses timed-entry tickets, and the first slot at 8 a.m. is the calmest and coolest time to visit, especially in summer. Late afternoon is another good window once the tour groups have thinned. A private guide can secure your entry time in advance and lead you through the Parthenon, the Erechtheion, and the Theater of Dionysus. Pairing the visit with the Acropolis Museum afterward puts the original sculptures in context.

Santorini’s views are hard to match, but the island can be crowded, especially when cruise ships are in port between mid-morning and late afternoon. Staying on the caldera rim lets you enjoy Oia and Fira in the early morning and evening, when most day visitors have left. Inland villages like Pyrgos and Megalochori, the Bronze Age site of Akrotiri, and the volcanic vineyards that grow Assyrtiko grapes show a different side of the island.

Meteora is about four and a half hours north of Athens by road. Six monasteries are still active, each perched on top of sandstone pillars that rise from the plain. An overnight stay in Kalambaka lets you see them at sunrise and avoid the midday tour buses. Visitors need to cover their shoulders and knees, and women are asked to wear skirts, which are provided at most monastery entrances.

Look for horiatiki, the classic Greek salad of tomato, cucumber, olives, and feta, along with grilled octopus at a seaside taverna and slow-baked dishes like moussaka. Each region has its own specialties: dakos, a barley rusk topped with tomato, on Crete, fava bean purée on Santorini, and loukoumades, fried honey dough, in Athens. Greek wine is worth exploring too, from Assyrtiko on Santorini to Agiorgitiko from Nemea in the Peloponnese.

Greece pairs easily with Italy, either by ferry from western Greece to ports such as Bari and Brindisi or by short flights from Athens. Direct flights from Athens also connect with Croatia and Egypt for a longer Mediterranean journey.