Greece

Greece does the classic Mediterranean trip better than anywhere. Athens for ancient ruins; the islands for beaches and slow lunches; the Peloponnese for an underrated mainland alternative; Crete for size and depth. Skip August unless you've prebooked everything.

The shape of the trip: two nights in Athens for the Acropolis and the food scene, then ferry out. A good ten days links two or three Cyclades by Blue Star ferry — Naxos for beaches and mountain villages, Milos for the volcanic coastline, Santorini if you must. Days settle into a rhythm of morning swims, long taverna lunches, and ruins at golden hour. The money goes to ferries and island hotels; eating well stays cheap if you eat where the Greeks do.

The honest part: Santorini and Mykonos in high season are a crush of cruise crowds and overpriced rooms, and ferry schedules bend your itinerary, not the other way around — build in slack. If you want efficiency and everything running on time, this isn't your trip. But May, June, September, and October give you warm sea, open tavernas, and half the people, and that version of Greece is very hard to beat.