Santorini and Mykonos are a steal during the fall, when both prices and crowds drop. Temperatures stay in the mid-to-upper 70s through September. Though it’s not a typical fall vacation (you’ll be swapping reds and oranges for blues and whites), autumn is an excellent time to visit the Greek Isles. The sea may not be quite warm enough to swim in, but you’ll still be able to take cruises around the islands, walk along the cliffs, and lounge on the beach. Plus, it’s quieter and less touristy, so you’ll get a better look at the local way of life. Discounts on rooms with beautiful views, and not having to wait for a table or tour, are also nice perks that come with visiting during the fall. Restaurants and shops will usually stay open until late October, but places will be less crowded and feel more intimate.
Our hotel pick: Canaves Oia Hotel
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