nirajshah8

I'll be heading to the Greek islands later this month and will be spending the entirety of my time in the Cyclades. I have the first half of my trip planned out and would love any insights on must see's / do's / and other recommendations. I'm a 34 year old male and will be travelling with two females of the same age range. We like to lead the life of "work hard play harder" and are eager to take in the scenic beauty of Cyclades as well as a bit of partying and nightlife. We're not people that require anything fancy or over the top, just a bed to sleep in and a roof over our heads, experiences matter more than anything else!
I've got the first half of our itinerary planned out and would love feedback or insight onto the latter half. The caveat is we need to be on Paros by May 25th for one week. Afterwards, we can island hop for another two weeks up to June 12.

Our confirmed itinerary:

May 13: Santorini
May 14: Santorini
May 15: Santorini
May 16: Santorini
May 17: Ios
May 18: Ios
May 19: Ios

Our hypothetical itinerary post May 19

May 20: One more day Ios / Milos
May 21: Milos
May 22: Milos
May 23: Naxos
May 24: Naxos
May 25-June 1: Paros
June 2-12: ???

KLouis

You seem to have a preference for the more populated islands. In that case, I'd certainly add Syros to the list. Nice island with a great city (Ermoupolis). If, on the other hand, you also want to experience an "empty" island, try places like Sikinos or Kythnos or... There are lots of that kind! I'd personally avoid Mykonos and, although already on your list, Ios. You realize, of course, that I'm not a party type.

nk15

My suggestion would be to cut down some of the island hoping, and a minimum of 4 days per island. So based on what you have I suggest 4 days Santorini, 3-4 Ios, 4-5 Milos (has a lot of good beaches; with a possible day trip to Kimolos), 1 week Paros, and split the last 10 days between Naxos and Mykonos, probably 6 Naxos 4 Mykonos, or 5 and 5. I think you have to include Mykonos, if you haven't been and you spend a month in Cyclades anyway.

6-7 islands is plenty and you hit reasonably well all the main ones. You are a little earlier in the summer season so hopefully the water is warm enough, but you also avoid the high season so it should be cheap enough.

jannosk

david55

While I realize you are focused on the Cyclades...it's a shame that you are missing Crete. With a whole month...there is plenty of time to add 10 days of Crete.

nk15

Indeed Mykonos and Santorini from mid July to end of August are crazy expensive and there are no Greeks on the islands, almost everyone is international tourists, lol...But outside these days there are great deals to be had, especially if you book in advance. But even in peak July/August season you can occasionally find some great deals there....

In Paros, I suggest you stay in Parikia (capital city/port) instead, it is beautiful, cheaper, on the water/on the beach, and next to the bus system, so you don't even need a car.