I'm rethinking my Greek island itinerary (again!) for next May/June. At first we were going to do 2 nights in Athens, 4 in Santorini, 4 in Naxos and 4 in Paros. Then I thought I would like to include Crete, so it would be 2 in Athens, 4 in Santorini, and 8 in Crete. I feel like 8 nights is alot for one island (even though it is big)-so now I'd like to include Naxos again and do 2 in Athens, 3 in Naxos, 3 in Santorini, and 6 in Crete. What do you think? Will 3 nights be enough time in Naxos and Santorini? Thanks so much for your help!

Lauren, I'm doing something similar later this summer - 3 nights Santorini and 5 nights Crete. From everything I've ready the time distribution you have is plenty. Enough time to see lots of each island, but to also relax and absorb the atmosphere.

Are you planning to make all your hotel reservations in advance or are you going to find accomodations as you go? In May it's easy to just arrive and find a room since it's not crowded yet, so if this appeals to you why not just go to the first island on your list and stay until you're ready to move on? Have some ideas of the hotels where you'd like to stay, get yourself an OTE phonecard (available everywhere) and call ahead to your next destination to reserve just before you arrive. This will give you maximum flexibility and put a bit of spontaneity into your adventure.

We prefer to make the hotel reservations in advance, but we might decide to just play it by ear. It just makes me nervous not having reservations. Thanks so much!

Just so you know, May is an easy month to go without reservations. I've done it so many times in Europe I've lost count. There are rooms available everywhere you go. If you were so inclined, you could pick up an OTE phone card when you get to Athens and call ahead to your next island to the hotel of your choice and make a reservation that way instead of booking so far in advance. That way you could come and go whenever you wanted but would still have a room waiting for you when you arrive.

I think your plan is sound and you are going to experience a wide variety of different Island experiences.