You’d have to check the schedule for your specific dates but I think Santorini then Milos then Paros then Naxos and Athens would probably be the best order. 3 days in each sounds great. Or a small tweak: 2 days in Milos and then 4 days in Santorini (splitting time between 2 of the 4 caldera towns) or even 4 days in Paros (splitting time between Naousa and Parikia).
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Mykonos had gay clubs and sunrise parties long before rave culture was even invented. Its bohemian allure hasn’t faded since the 1960s, although the once naked beaches now have nail bars, personal trainers and house music pumping out all hours. The influx of supermodels and superyachts has inspired hot new hotels and restaurants. The hippest place to show off your abs is Scorpios, a louche beach bar that puts Ibiza's finest in the shade (book a cabana to watch the sunset). After hours, it's always Astra, where you might find Keith Richards chatting up Karolina Kurkova. The gay crowd has dwindled, but drag queens and oiled bodybuilders make a splash at Jackie O, overlooking Super Paradise bay.
Considering your interests (great food, hiking, beaches, nightlife unimportant) then Naxos should definitely be your other island. (And Naxos has many daily ferry connections with both Santorini and Athens.) Also, Athens needs at least one full day to explore so you should drop any thoughts about Delphi or Nafplio. Also, I would look into flights from Athens to Santorini on your night of arrival. If you could get to Santorini that night (and move your day in Athens to the end of your trip) you’d almost gain an entire day and could spend two nights on Naxos.
Folegandros – which means ‘iron hard’ in ancient Greek – is as barren as its name suggests. Fruit trees are protected from fierce winds by rings of stones. You won’t find sandy beaches lined with sunbeds; only limpid, pebbly coves, such as Katergo, Ambeli and Livadaki. Water taxis service some beaches in high season; otherwise you’ll have to scramble down rocky footpaths to cool off. On your way home, stop at Synantisi in Ano Meria for the island speciality of matsata (goat or rabbit stew with hand-made pasta).
The village square should be your first port of call on any Greek island: settle into your favourite café, pick up local gossip, and adjust to the languid pace of life. On Folegandros, this presents a challenge: the cliff-hanger capital, Chora, has not one but three squares, each brimming with a jumble of cafés, tavernas and dinky raki bars. We recommend Pounta (pounta.gr), where the Danish owner makes (and sells) the lopsided cups and bowls in which your coffee and Greek yogurt are served. From Chora, zigzagging steps lead up, up and away to the only real landmark, Panagia church; make the pilgrimage at sunrise (perhaps after an all-nighter at dimunitive Astarti bar).
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Java, with a population of 140 million, makes its first appearance on this list. Celebrated for its ancient culture, breathtaking vistas, and UNESCO World Heritage sites like the Borobudur Temple Compounds, the island also offers the opportunity to indulge in modernity (five-star hotels abound). Waterfalls, volcanoes, protected parks, and white-sand beaches also allow visitors to get away from the thrum.
Hi Dave! Your website is so detailed and helpful! I’m starting to plan a trip for late May-early June. We were interested in visiting Santorini, Naxos (we opted for Naxos instead of party-filled Mykonos) and Milos. Our main airport of arrival is Athens. What order should we visit all three islands (in terms of convenience of ferry/flight availability) and how many nights do you recommend allotting to each? Thanks in advance for your time!
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My husband, another couple, and I are planning a trip to Greece in September 2017. We are staying in Milos for a few nights and were planning on staying at Melian Hotel and Spa….do you know anything about this hotel? I was worried about proximity to things, but it looks like no matter what, we are going to need to rent a car or use the bus system to get around. It seemed though that Melian had 6 or 7 restaurant options within walking distance. Also, any ideas or tips on things to do, see, or go?? We plan to do one of those semi private sailing tours, but other than that we are an open book. Thanks so much for any input!