Summer (July - August) is the busiest season in Greece when popular destinations like Santorini, Mykonos and Rhodes are full of tourists. August is the month when the locals take their annual leave and add to the crowds of visitors.
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In order to avoid the heat and crowds, I suggest visiting in the spring (April to June) or fall (September and October). I think April and September are the two best months — the weather is fantastic, but you get a better travel experience away from the cruise-ship crowds of July and August.
Tourist season in Greece is roughly Easter through October. Peak season is summer, when Athens is packed with tourists, and hotel prices can be high. July and August are the hottest. The best time to visit is late spring (May) and fall (Sept–Oct).
Greek islands which are smaller and less touristic have a shorter season, larger islands like Crete, Corfu and Santorini have extended seasons sometimes up to full year. Hotels have different opening/closing dates but the general rule for islands is that they open in April and close at end October.
The best time to visit the Greek islands, like Santorini, Mykonos, Corfu and Kefalonia (Argostoli), is in October when the weather is still warm and the crowds are few. The Greek islands are an all-year-round vacation destination, with temperatures ranging from 50°F (10°C) to approximately 100°F (38°C).
Winter (November - March) is the low season of sunny Greece. While the big islands like Crete, Rhodes and Corfu entertain visitors all year round, the smaller islands wind down for winter. This would be a wonderful time to visit Greece for a laid-back holiday if you don't mind the cold.
The cheapest months to book a flight to Greece: September and October, followed by November. Booking a flight in September can see as much as 13% savings compared to the average yearly flight price. The most expensive months to book a flight to Greece: May and June.
Kefalonia. Kefalonia is one of the largest Greek islands, but one of the lesser-visited. This means that you can explore the island's rugged mountains, fir forests and magical caves in peace, away from huge huddles of tourists.
The most affordable Greek Islands to visit include Crete, Andros, Tinos, Corfu and Naxos. These cheap Greek Islands don't get nearly as many visitors as others, making everything from transportation to food and accommodations more affordable. And often, they're not even very far from the more popular islands.
So, how much does it cost to go to Greece? Based on my estimates, your Greece costs will be about $4,455 per person for two weeks. Remember, this estimate is based on visiting the most popular islands (Santorini and Mykonos), which are also the most expensive.
Winter (late October through mid-March) is colder, with some rainfall. Sights may close during lunch, tourist information offices keep shorter hours, and some tourist activities vanish altogether. Hotel rates are soft; look for bargains.
With average daily high temperatures in the mid-70s Fahrenheit, it's usually still warm enough in early October to sunbathe in comfort and to dine outside at night, with little chance of rain. By mid-October the Ionian and Aegean seas are cooling quickly; if you love to swim, go early in the month.
Greece is glorious all year round and in October you can enjoy high temperatures and sea that won't chill the bone when swimming. Kos, for example, has an average high of 26ºC to go with 8 hours of sunshine.