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.
I’m a little worried I’ll get bored in Milos. My husband likes to stay in one place, but I like exploring. We would have split our time more evenly but we want to stay on the caldera and it’s just too expensive to stay any longer than two or three nights. Alternatively, we could stay in Santorini for longer but move to a cheaper hotel. Perhaps Santorini 6 nights and Milos 6 nights?

You seem to have your heart set on Zakynthos but I have to say it’s not a good use of time for a sort-of overrated payoff. Your time is much better spent (in my opinion) seeing another Greek island in the cyclades (maybe taking a ferry to Naxos or Paros sitting outside on the deck drinking a bottle of wine) rather than taking a bus and connecting flights. Zakynthos and Santorini/Mykonos are on opposite sides of the country and the only way from one to the other is by flying (or some combination of bus and ferry). So, my recommendation is to consider spending those Zakynthos days in Naxos, Paros, Milos, or some other Cycladic island.

Sarah-Jane — Thanks for another helpful article (this one on planning an island-hopping trip). Chasingthedonkey.com is a great website and my first go-to place for information on Croatia. I have scheduled my third 3-month-long stay and still have so much to do and see in Croatia. Personally, my favorite times to visit are in the “shoulder” seasons …. September-November and March-May.


If the glitzy excess gets too much, escape to Fokos taverna for superfood salads and lamb chops, or Kiki's, an off-grid grill-shack overlooking Agios Sostis bay, where even Naomi Campbell has to queue for a table. Or cruise over to the tiny island of Delos, an archaeological sanctuary that once thronged with 30,000 sun worshippers (the temple is dedicated to Apollo, the Greek god of light).
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.

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Where to stay in Patmos: Archontariki is a gorgeous, five-suite hideaway in Chora. If money is no object and privacy is paramount, Serendipity has the most exclusive villas. . Petra, an 11-suite resort overlooking Grikos bay, is run by a charming local family who treat guests like friends (plying them freshly baked sweet cheese pies). It’s where Jean-Paul Gaultier prefers to stay.
Aside from coral, there is a lot of history in Zlarin, dating back to the 13th century. If however, you’re more about beaches and beauty, then Zlarin has it covered, and then some! The long sandy beach is ideal for families who want to run free and explore, and the green background gives you that ‘castaway’ feel. You won’t find a lot of hotels on the island, though. Instead, there is wonderful private accommodation, which helps you get that home-away-from-home vibe to your break.
I’m a little worried I’ll get bored in Milos. My husband likes to stay in one place, but I like exploring. We would have split our time more evenly but we want to stay on the caldera and it’s just too expensive to stay any longer than two or three nights. Alternatively, we could stay in Santorini for longer but move to a cheaper hotel. Perhaps Santorini 6 nights and Milos 6 nights?
Where to stay in Crete: A 300-year-old hamlet surrounded by olive groves, Kapsaliana Village Hotel exudes peaceful authenticity. On a sandy bay just beyond Chania, Ammos Hotel smartly combines Scandi chic with a child-friendly vibe. Blue Palace Resort & Spa beats the (stiff) competition in Elounda with its spiral stone Isola Beach Club, thalassotherapy spa, and boat trips to Spinalonga island, a national monument just across Mirabello Bay.
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