Best island(s) to visit in the Greek Isles/Cyclades in late september

September 3, 2018 11:32 AM

Greece and the Cyclades have been discussed previously on Ask MeFi visit but we have a specific request for suggestions for the best island(s) (possibly two) for a week long adventure from Athens to Crete in late September.

As mentioned we have about a week to get from Athens to Crete and plan to stop on one or more islands along the way. We prefer more upscale settings and quiet peaceful places.

If you have a recommendation for a specific island, town, and especially hotel or Air BnB or similar for late September please share. Tips for Crete are welcome as well.

We understand that visiting off peak presents unique opportunities (less crowds) and challenges (islands emptying out) thus the question.

posted by specialk420 to Travel & Transportation (6 answers total)

Last year I visited Amorgos and it was perfect. Breathtaking beaches, scuba diving, small towns to explore, good food, music, hiking, historic sites, friendly people.... everything I wanted in my Greece vacation. We stayed at the Aegialis Hotel which is a 5 star resort and spa - Just look at the front page of the website, seriously. Now the island is pretty sleepy, so you're not going to get crazy all night dance parties or world class shopping or whatever but.. if you want quiet, peaceful, and gorgeous, Amorgos is the place to go.
posted by silverstatue at 5:26 PM on September 3, 2018

thanks silver statue - amorgos is on the short list! what time of year did you go?
posted by specialk420 at 9:25 PM on September 3, 2018

So, I haven’t visited these places in late September but based on your criteria you might like:

-Folegandros. Lovely scenery, great food (rooster in red wine sauce with homemade pasta is the local specialty), pretty chora town. Try the Blue Sand Hotel for an upscale-ish boutique experience. We went after our wedding.
-Hydra. No cars allowed, very beautiful and laid back. Popular with the yachting crowd.
-As linked in your post, Sifnos might appeal. Very pretty and hilly, more for you to explore, gorgeous sandy beaches. I don’t know about upscale, but I bet there’s something.

I loved Koufonisia when we visited 7 years ago, but it’s very small and you may get bored if you’re not beach people. There’s maybe two bars, and a smattering of tavernas. We still daydream about its perfection, though.

With your priorities, I would give a hard pass to Kos, Zakynthos (just got back - very much geared to British tourists who want to stay in the pub or club), Mykonos, Ios, and in my opinon, Santorini (everyone claps for the sunset - why?? - and it’s way too difficult to get a decent freddo cappuccino - am I even in Greece???).

Kephalonia would be a maybe. Was there 2 weeks ago, loved Assos and Myrtos once the crowds cleared out and they have a nice local white wine. Geared to middle class Italian tourists. The Ionian in general feels more Italian-ish to me.

For context, I’m a 34 year old American living in London married to a native Greek; we travel inexpensively but prefer a more Greek experience on summer holidays. On holiday in Greece, we get freddo cappuccinos first thing because priorities, find a nice bakery and bring some tiropita to the beach, laze about reading and swimming for a while, go back to our hotel to eat some fresh tomatoes and local cheese and wine on the balcony, and then go to whatever taverna catches our eye and maybe a trendy bar or wine place for a nightcap. I will sometimes drag him to a museum or historic site.
posted by Concordia at 1:01 AM on September 4, 2018

@concordia - thank you for the great suggestions.

Given that we have a week from Athens to Crete, what do you think about 1 island between athens and crete with a possible afternoon/day stop in Sanotorini to catch the boat to Crete?

Also - thoughts on Crete? do we need a couple days there? or save it for a future visit? We are flying out Chania.
posted by specialk420 at 9:33 AM on September 4, 2018

Crete is pretty big, you could easily spend a week there. You can visit Knossos and the museums in Heraklion, swim in the cold cold beaches in the south part of Crete, see the palm tree forest in Vai, visit the old town in Rethymnon and Chania, go hiking in the Samaria Gorge, etc...
I grew up in Heraklion (north) and spent my summers in Ierapetra (south), now I live in Athens.

If you're staying in Athens, you can take the ferry and make day trips to Aegina and Agistri. Go for a swim, have a bite to eat, swim again and go back to Athens before it's dark. Tickets were about 15 euro one way last time I went there, they might be more expensive now, though.
posted by marouli at 6:32 AM on September 5, 2018

I was in Amorgos in late August into early September of last year. So right about this time :) We flew into Athens and then took a six hour ferry to Amorgos. If you want more info, memail me!
posted by silverstatue at 4:55 PM on September 5, 2018