To sum up: a lot depends on your own stamina because island hopping means packing and unpacking, getting on and off buses and ferries. Limit your choice of islands to perhaps one or two less than you think you can manage. Maximise transport links to avoid backtracking or port-transferring and since you are traveling high season be aware that you will usually need bookings ahead at most places. It is possible to turn up on an island and not find a place to stay or have to make do with a third-rate option. 

Chania is a great choice. A wonderful charming town. Elounda is great for a quiet laid back stop, Agios Nikolaos has a more interesting vibe and is more of a real town. Also very charming. I prefer Ag Nik but Elounda has more luxurious hotels. (Crete hotels.) Naxos has lots to see in the interior so if you didn’t explore then certainly consider that. Folegandros and Milos are both incredible. Folegandros is more suited to walking and relaxing (and has some top notch restaurants and hotels). On Milos you need to do a tour and get out and actively explore to do it justice. Geologically Milos is stunning. A little like Santorini but with better beaches.

Despite Zlarin’s small size and relative obscurity, it is certainly an island with dazzling beauty. It is known locally as the ‘Golden Island,’ because it’s really that eye-wateringly gorgeous! This small island is just off the mainland, separated by the Sibenik Channel and is mostly famous for its history of coral harvesting; there is even a Coral Museum where you can learn more about it.


Tinos has more than 50 villages, each vying to be fairest of them all. In Pyrgos, famous for its marble craftsmen, sculpted birds and flowers decorate every doorway. In Volax, basket weavers squat outside cottages carved from giant boulders, seemingly flung from the heavens by Zeus in a fit of pique. There's even a village called 'love’, Agapi, where you can tuck into wild-fennel fritters at the only taverna. Tinos takes its food culture seriously: there are artichoke, caper and honey festivals. For a perfect meal in perfect surroundings, go for cuttlefish risotto and octopus caramelised in grape must at Thalassaki, served on the jetty in Isternia bay, then watch dusk bleed into the horizon from Exomeria bar.
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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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