When to go
April to June and September to October give the best balance of warm days, softer prices and fewer people on the cliff paths. Midsummer is hot, windy and crowded, especially on days when several cruise ships anchor off Fira. The main caveat runs the other way: from November to March many caldera hotels close entirely, and unheated plunge pools are too cold to use in early spring or late autumn, so confirm both opening dates and pool heating before paying for a pool suite.
Getting there
Most visitors fly into Santorini Airport, either direct from European cities in season or on a flight of under an hour from Athens. A pre-booked car takes roughly 20 to 35 minutes to reach Oia and less to Fira or Imerovigli. Ferries from Piraeus take around five hours on the fastest boats and dock at Athinios, below the cliffs, so add a winding road transfer. Many hotels sit down steep steps from the road, which means porters carry the bags; pack in soft luggage if you can.
Where to base yourself and for how long
Oia is the postcard village with the most restaurants and the biggest sunset crowds. Imerovigli sits higher, calmer and more central, with an easy walk into Fira. Firostefani, between the two, is a useful middle option. Three nights covers the views and a boat day; four or five lets you add wineries and the south coast without rushing. We wouldn't split hotels unless you have six nights or more.
