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They’re all great choices. Athens (1 to 2 full days) is great for historical sightseeing. Mykonos for beaches and nightlife (2 to 4 days). Crete for historical sightseeing, greek culture and towns, some beaches but spread out (4 to 7 days). Santorini has great sightseeing, tours, and some history (4 to 7 days). If visiting outside of June to September then drop Mykonos and do the other 3 for sure.

Glass-bottom boats with thatched canopies ply shimmering lagoons. Tanned locals in pareus (sarongs) play ukuleles. Ridged velvet-green mountains punctuate the skyline. Palm trees reach higher than any roof. This is reality in the Cook Islands, a 15-isle archipelago marooned in the South Pacific. Go on a mountain safari on the main island of Rarotonga, or head to Aitutaki to stay in an overwater bungalow and motu-hop to deserted sugar beaches that beg to be Instagrammed.
Less than two hours from Athens, Hydra fills up with chic Greeks at weekends. . They come to disconnect and slow down, but also to see and be seen. Wily cats and weary donkeys patrol the back alleys, but all the action happens along the waterfront. Oh look! There's Olivia Palermo at The Pirate Bar and Chloë Sevigny shaking her tail feather at Hydronetta beach bar. Who cares if there are barely any beaches? You can always find a slab of sun-baked rock from which to leap rock from which to dive into the clearest water in the world. 

Comfortable accommodation in May for 2 persons can be found for between €40 and €80 per night. A meal for two that includes a starter, two main meals, salad and a litre carafe of local wine will cost you around €25-35. This can vary widely depending of level of establishment you eat at. A cheap vegetarian dish (pulses or vegetable) will set you back by no more than €5-6 a plate. If you get your breakfast included at the hotel, that is good because breakfast can add another €15 for the two of you per day.
Hi Dave. Thank you for your amazing website! We (30’s / 40’s couple – no kids) used your recommendations last year in September and visited Santorini (7days), Milos (3days) and Crete (12days) before spending 3 days in Athens. The trip was amazing and Greece is calling us to go back again this year! We have a conundrum which we are hoping you can assist (well, many of them really!)
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Yachts moor in the deep, sheltered harbour of Vathy, or Kioni, a miniature port where you’ll find Spavento, the perfect pier-side café-bar. Go any time of day or night for ice-cream sundaes, excellent cocktails, and a soundtrack to make your heart sing. Ideal for low-key family holidays or retreats, rugged little Ithaca is somewhere you can still disappear.

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