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Sifnos owes its foodie reputation to its most famous descendant, Nicholas Tselementes, who wrote the first Greek cookbook in 1910. Forget souvlaki and moussaka: here, chickpea croquettes and stewed capers are taverna staples. The island is peppered with potteries that produce the earthenware casseroles used for revitháda (baked chickpeas) and mastello (lamb with red wine and dill). Traditional dishes are slow-roasted in a wood-fired oven at To Meraki tou Manoli, a local institution on sheltered Vathy bay. (While you’re there, invest in some timeless tableware from Atsonios pottery, in business since 1870.)
Ferries between Naxos and Milos don’t start until June 7th (one each way, every day after that). Ferries between Santorini and Milos start April 28th and there is one every day in each direction. And there are always ferries between Naxos and Santorini. So if the dates work I would fly to Santorini (the longest leg) then ferry to Milos then Naxos and back to Athens. But if you need to travel between Naxos and Milos before the 7th then ferry Athens to Milos to Santorini to Naxos and back to Athens.
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).
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).
This quiet island is waking up. Luxe boutique Zemi Beach House recently opened with classic details and a laid-back vibe that call to the local natural beauty of Shoal Bay East beach. On Merrywing Bay next to sister property CuisinArt Golf Resort & Spa, The Reef by CuisinArt recently unveiled 80 new suites. Here, farm-to-table fare means local fish and fresh produce from the on-site Hydroponic Farm. The Four Seasons Resort and Residences Anguilla took over the former Viceroy Anguilla with villas that overlook white-sand beaches and the rugged coral coastline.
We are planning to come back at the start of September for 2 weeks to visit different islands for some beach and sun. To give you some background, we loved Santorini, Milos and the quieter / smaller places in Crete (Loutro, Falassarna, Samaria Gorge). We enjoy beach time, some hiking, site seeing, good wine / food and good / buzzy atmosphere at night for dinner / tavernas.