I think that’s a great plan. Santorini is a must and Milos and Naxos are two islands that have both great beaches and lots to do and see away from the beach. Renting a car and exploring the interior villages of Naxos is a must-do and so is a boat tour around Milos. If you’re willing to cut Athens to 2 days, I would recommend Santorini 5 days, Milos 3 days, Naxos 3 days, and Athens 2 days.

Another South Pacific island group (see a pattern here?), the Cook Islands are pretty far off the map. OK, not too far, but they are considerably less visited than some of their neighbors. These tiny islands are named after James Cook, the intrepid man who discovered them. With few amenities, this is the best place to find your inner castaway and escape modern life. The islands see similar weather to the rest of the area, with temperatures hot and humid all year round.
Patmos has an indefinable je ne sais quoi - an otherworldly quality that radiates from its crowning glory, the medieval monastery of St John. This turreted fortress, bursting with Byzantine relics, is named after John the Divine, who conjured up his apocalyptic revelations in a cave nearby. Pure-white Chora, a World Heritage Site, is where A-listers and fashion editors stay. High walls and heavy doors conceal magnificent mansions dating back to the 16th century.
Close to this island is a little island that provides excellent snorkeling opportunities. You may even spot a few reef sharks. Bathtub-warm water and fine sand beaches kept me here for over three weeks. It will do the same for you. Visit between November and March for the best weather and the fewest people. May through October sees a harsh monsoon season that shuts the island down. The best way to get there is by boat from Pak Bara.
Where to stay in Crete: Adults-only Casa Cook is a chic little number that breaks all the rules about package holidays (you’d never know it was created by Thomas Cook). The Marco Polo is a 15th-century mansion decorated like a pasha's harem, with an enchanting garden restaurant. Ottoman-style suites at Melenos Lindos have hand-painted ceilings and carved platform beds.
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Thank you for putting together such a great site. My husband and I are planning a trip to the Islands in May – neither of us have been and, honestly, have no idea where to even start putting together an itinerary. We have at least 14 nights to spend there (and may be able to push that to 17). I’m in my early 30s, my husband’s in his early 40s. Our priorities are culture and history, swimming, beautiful views, nice towns, and food and drink. We’re not interested in clubbing at all, but more laid-back late night bars definitely appeal. This is probably our one big holiday this year so while the budget is more mid-range than sky-high, we can push it a bit for the right places or experiences. We’re happy to take in quite a few islands, or with a mix of longer and shorter stays. 
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