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.
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.
On Syros, capital of the Cyclades, you won’t find sugar-cube villages and whitewashed lanes. The colourful 19th-century city of Ermoupoli is built on twin peaks – one Orthodox, the other Catholic, the heritage of a long Venetian occupation. There’s still a strong Italian flavour in Ermoupoli’s marble piazzas, princely mansions, and miniature replica of La Scala, the showpiece of a year-round cultural scene. Syros hosts festivals of animation, dance, digital art, film, classical music, jazz and rembetiko, the Greek blues popularised by local musician Markos Vamvakaris. A few rembetiko joints have survived in the upper town, Ano Syra.
Nicknamed “The Helen of the West” (an allusion to the beauty of Helen of Troy), St. Lucia stuns with its signature feature: the UNESCO-listed twin Pitons. Reaching heights of about 2,500 feet, the voluptuous volcanic spires complement the island’s other attractions, including verdant jungles, sparkling silver-sand beaches, haunting sugar-estate ruins, and a mineral-rich natural mud bath. Meanwhile, the island’s most famous resort, Jade Mountain, is an architectural gem in its own right.
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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.