Two weeks is a great length for a Greek vacation. You'll have plenty of time to see multiple islands and historic mainland sites, taking part in cultural or outdoor activities along the way.
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There are many wonderful sights on the mainland, e.g. Meteora, Delphi, Olympia, Nafplio, to name just a few. Four weeks would also give you more time to get to know each island — a 2N stay gives you only one full day of sightseeing. Think quality rather than quantity.
If you're island hopping the Cyclades, leave three days aside to get a real taste of all the islet has to offer. For those planning a single-destination getaway, we'd recommend staying on the island for five days plus.
Santorini is the top tourist destination in Greece and is world-famous for its unique natural beauty. The caldera with the white villages on top, the sunken volcano, and the charming sunset make it a popular place for vacation. In brief, we recommend staying 3 to 5 days in order to visit as many places as possible.
1. Athens: where to go in Greece for first-timers interested in culture & variety. Considered by many historians to be the birthplace of Western civilization, Athens is an ancient city practically overflowing with culture. Remnants of Ancient Greece are prominently spread throughout the city's narrow stone streets.
If you only have one week in Greece, stick to Athens and the islands of the Cyclades, and you'll get a well-rounded glimpse into everything that Greece has to offer. Spend two days in Athens, two in Santorini, two in Naxos, and one night enjoying dinner and drinks at the water's edge in Mykonos.
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.