It’s best to visit Greek islands within the same group. For example, I wouldn’t recommend visiting Corfu and Santorini on the same trip as they’re on opposite sides of the country. Instead, visit islands in the same island group: the Cyclades, the Sporades, the Dodecanese, the Ionian, the Saronic, and the Northeastern Aegean. For one, they’re close to each other. And two, they have frequent ferry connections with each other. For first time visitors to Greece, the Cyclades make the most natural and convenient introduction.
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).
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).
Yes, I would agree that 8 or 9 days is too long for Naxos – unless you’re happy sitting at the beach for several of those days. But if you’re looking to be semi-active and explore then you’d be best to add Paros and spend 4/5 days on each. Crete, on the other hand, would be perfect for an 8/9 day road trip. Start in Heraklion (where the ferry arrives from Santorini) head east and then south and finally ending up in the western town of Chania where you can fly up home from.
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As a starter to explore ferry services, go to the Ferryhopper.com and punch in your route searches. Note: air travel between islands is not generally good. Air travel is normally only feasible between Athens (or other mainland destinations) and the island in question. Some exceptions do exist – Rhodes Kastellorizo, Kos-Leros-Astypalaia, Thessaloniki-Limnos-Ikaria etc. but again you will need bookings weeks in advance.
Another South Pacific island group (see a pattern here?), the Cook Islands are pretty far off the map. OK, not too far, but they are considerably less visited than some of their neighbors. These tiny islands are named after James Cook, the intrepid man who discovered them. With few amenities, this is the best place to find your inner castaway and escape modern life. The islands see similar weather to the rest of the area, with temperatures hot and humid all year round.
The almighty church has kept nightlife in check. If you must see and be seen, head to quietly glamorous Astivi or Stoa bar, on miniature Agia Lesvias square, in Hora. Beach life is generally languid and low-key; Psili Ammos and Livadi Geranou are our favourite hideouts. Dinner reservations are essential at Benetos, for Med-Asian fusion on an organic farm, and Lambi for grilled fish on a purple pebble beach.
I’m sorry if you covered this in another part of your site, (either I’m technically challenged or there just isn’t a search function for your site) but I’m curious about Corfu. From what I can tell, you mentioned it once in your site under your post about best beaches. The Paleokastritsa area is something that has caught my attention for a while and is on my list, and then I saw pictures of Nissakids Bay and that looked kind of amazing.

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.
Can you see all the major sights in Athens in one day? No. But you can see the Acropolis, Acropolis Museum, and the top historical sites of the Plaka in one day. If you had an extra half-day then visit the Archaeological Museum in Exarcheia. That still leaves many great sights but you will have seen all of the iconic Athens attractions. Adding Naxos is always a good idea. You might even enjoy it more than Mykonos (but no nightlife like Mykonos).
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Hi Dave! One more question, do you know of any resorts with heated pools or private jacuzzis/pools in the room that are heated on islands other than Santorini and Mykonos? Looking for something above 26/27 degrees and can’t seem to find any! Elounda Beach resort said they could heat the private pool but it costs 45 EUR per degree! Hoping you know of another option that would allow us to swim comfortably in Early June. Thank you!!
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.
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!
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