Small Cyclades islands in May?

No, it won't be too early but your time will be best served if you focus on one island group. Since Santorini and Naxos are on the list then obviously the "Small Cyclades" islands are your logical choices. You're on the right track with those on your list, but don't exclude Donusa and Anafi when you're choosing. A copy of T. Cook's "Greek Island Hopping" should help you figure it out.

Thanks Lee. I should probably get an updated version of Thomas Cook -- mine is from our first trip to Greece in 2003. If you have any tips regarding those smaller islands I would love to hear them!

Thanks, John. I've never used Rough Guides but will check that out. In further research I have learned that Astypalaia is dead until mid-June, so I'll drop that, but the rest seem fine. I've looked at ferry connections and they seem workable.

Right now I need to decide how many nights per island. Our route will likely be Rafina>Andros>Naxos>Amorgos>Santorini> Folegandros>Milos>Athens. Not sure how or if to fit Koufonesia or Anafi.

Any comments or suggestions are welcome!

That's a lot for 27 days, especially when you subtract transit time from one island to the next. Don't forget to calculate the time it takes to check out of your hotel, make your way to the ferry port, go to the next island, find your next hotel and settle in. It adds up. You will basically lose 1 day of your holiday for every island you visit. Add to that the return to Athens, which should be at least a day in advance of your departure from Greece, more if you plan to explore the city at all. And in that regard save all your time in Athens for the end so you aren't backtracking and so you don't have to stress out about returning to the mainland at the last minute for your flight out.

It does look like a lot. We've done 4 islands in 18 days a couple of times and it didn't seem too hectic, but we were younger then. :) I'll wait & see how the ferry schedules look next spring.

One more question: if our plane leaves early on June 7, would you return to Athens on June 5 or 6? We'd probably be coming from Milos. On our first few trips, we always returned 2 days ahead (i.e June 5). The last few times, we've flown back to Athens the day before our homeward flight, but that really doesn't give any buffer for transportation issues. I'm curious what other travelers do?

I think most travelers, myself included, take the risk and return to Athens the day before their outbound flight, and it usually works fine. Bad weather that might delay a ferry or plane usually happens in July or August, so in June if you have no need to spend more than a night in Athens it will most likely work for you as well.

Also, even bad weather rarely stops the flights and larger ferries. It's mostly the smaller highspeed catamaran ferries and Flying Dolphins that are susceptible. In that regard avoid the SuperJet2 and FlyingCat4 if the seas are rough.

Thanks, Lee, that's good to know. I appreciate your help.

We spent most of a week in Koufonesia, it was great, but mainly for just chilling on the beach and relaxing. There are a few reataurants, a few shops, but no real sights or history, just great, mostly deserted beaches.

You get there mainly by small ferry from Naxos, schedule is somewhat limited, we found that to get there, coming from Mykonos, we had to stay a night in Naxos to make the connection, then back to Naxos to catch a late ferry to Santorini. Ferry burns up the day, so really, plan minimum of three nights, maybe four, depending on the days the ferry runs...not a destination for two nights only.

10 years ago, we found Lets Go to be a great guide, little more informative and focused than lonely planet. We were there in September, but May would be about the same, June busier.

Thanks, Paul. I was debating between Koufonesia and Folegandros, as I'm looking for a little island in between Santorini and Milos. But I think ferry connections will be easier with Folegandros.

I will look at Let's Go ... I thought it was more of a student guide, but if I can get it at my library, it wouldn't hurt to get another viewpoint.

If you want something small and very traditional check out Sikinos. It's in between Santorini and Milos. There's not much going on but there's a calm village beachfront, a couple of restaurants and hiking trails to other nearby beaches. There are only 2 villages, one at the port and one at the highest point of land. I enjoyed my stay there at Galini Rooms. I was there in May and the room was €15/night. It was very clean with kitchenette, TV, balcony and a great view of the port.

Wow, that sounds perfect. Not sure how I overlooked it but I will definitely take a close look at Sikinos now. Thanks Lee.