Hi! I have fallen in love with the cyklades and have visited Santorini, Ios, Naxos and Folegandros in late june. Folegandros was the best, a fantastic island. We are now thinking about going to Paros the last week in September. Naoussa seem to be a great place. What’s the weather like in late September? Is it still quite warm? I also wonder about the sea conditions. May the sea be rough at that time of the year? I don’t like wavy ferry rides 😨 Thank you for a good sight!
I would recommend Naxos over Mykonos and with 12 days you could easily add Paros too. With Santorini, Paros, and Naxos you’ll get a good mix of different delights and some ferry island hopping too which is fun in itself. 1.5 days in Athens is perfect for most – 1 day for the Plaka, Parthenon, Acropolis Museum area; and a half-day to visit the Archaeological Museum which is a short drive or walk from the Plaka but hard to fit in one day along with the other sights. 

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Crete, Santorini, and Naxos look quite doable within the 12-day block, but Crete’s beaches are scattered throughout a very LARGE island, Santorini really only has Kamari and Perissá (and some southern coast bays) and Naxos does have nice places to swim. If you choose only to visit those three islands in your relatively short time, you will do well.
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.

Between Nydri and the next main tourism centre is the little port and beach of Mikros Gialos (small bay) that is a great little base for individual travellers for a day or three. The port village of Vasiliki on the southern underbelly of Lefkada is a haven for windsurfers: see this page or this one for more information. The little village is very pretty and is a good base for general holiday-making (as are the two other places). From Vasiliki there is a regular local ferry that runs to Fiskardo on Kefallonia (via Ithaca/Ithaki).


Cooing American and Chinese honeymooners line up to take selfies as the sun sinks behind Santorini's caldera, the flooded volcanic crater. That view may be a romantic cliché, but it still takes your breath away. A volcanic explosion blew out Santorini's heart 3,500 years ago, leaving black-sand beaches, vertiginous cliffs in psychedelic hues, and swirling rumours about Atlantis in its wake. The eruption also preserved the ancient city of Akrotiri under layers of ash, and created fertile ground for exceptional Assyrtiko grapes and Vinsanto wines. (Sample them at Sigalas and Vassaltis wineries, paired with delicate dishes that let the grapes sing.)
The Greek islands have beautiful weather in the months just before and after peak season. It’s a great time to see the islands, save money, avoid the crowds, and still have great weather (though not as hot as July and August). If you want to see the super-popular islands of Santorini, Rhodes, Corfu, and Crete without the tourists then this is a great time to visit.
Hi Dave! One more question, do you know of any resorts with heated pools or private jacuzzis/pools in the room that are heated on islands other than Santorini and Mykonos? Looking for something above 26/27 degrees and can’t seem to find any! Elounda Beach resort said they could heat the private pool but it costs 45 EUR per degree! Hoping you know of another option that would allow us to swim comfortably in Early June. Thank you!!
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.

Tinos is only 15 minutes from Mykonos, so it's a wonder it isn't overrun with tourists. The harbour is swarmed on 15 August, however, when Orthodox pilgrims flock here to kiss the icons at Panagia Evangelistria monastery, one of the holiest sites in Greece. Otherwise, the island is miraculously untouched. Solitary chapels and whimsical dovecotes stud thyme-scented hills, dropping to sandy bays whipped by the meltemi wind. There's a nascent surfer scene on Kolibithra bay, where a VW camper van has been converted into a cute beach bar.


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I’m traveling to Greece for the first time, and I’m so fortunate to be staying for about 9 weeks (peak season, unfortunately, I’m an educator and it’s summer!). I have ample time planned in Athens, and the Peloponnese (with rental car). Here’s where I need some help and suggestions. I have 5 weeks saved for the islands and I’m still trying to figure out how to spend them. I’m not sure if I’d like to cover just a few islands and soak them in a bit deeper with longer stays…or to travel at a quicker pace covering several islands in each main area (the Cyclades, Ionians, Crete-Rhodes Dodecanese, Eastern Islands) I’m an easy traveler and enjoy diversity. I crave spending time with locals and interacting with families – home stays at times, I enjoy the water and I’m an avid diver, I like hiking and exploring. Also, want to perhaps relax a bit – food/wine tasting welcomed). I’m excited about the trip and my ideas are racing all over. Do you have some ideas and suggestions to share? A rough sketch itinerary for Greece? Thanks so much! 
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