What is your favorite Greek island?

Julie, You might have a look at Matt Barrett's Website, as that provide an excellent description of the "character" and features of many of the Greek Islands. I visited Naxos and Santorini earlier this year, and would highly recommend both. Naxos is one of the largest of the islands and has an interesting history and a good range of Hotels and restaurants. Santorini also has an interesting history and tends to be a bit more "upscale". There are a lot of VERY expensive shops in both Fira and Oia! The ancient historical site of Akrotiri was closed during my visit, but not sure whether it will be open in August? August will be peak season, so pre-booking Hotels would definitely be a good idea! I decided to try booking through one of the Greek Travel Agencies recommended on Matt's website, and that worked really well. They took care of not only the Hotels, but also transfers and Ferry tickets. Good luck with your planning

Another Naxos lover - Venetian influence (well what's left
from the 15/16C); great beaches; kitros; sweet inland
villages; and much more.

Amorgos is a lovely island - gorgeous scenery for starters
and off the beaten track except for Northern Europeans who
like bathing au natural. Quiet at night.

Paros is great but very popular.

The only island I wasn't enamoured with was Samos.

Mykonos is lovely and worth visiting, but Santorini is breathtakingly beautiful. We stayed in Oia at the Aspaki Hotel (check it out on Trip Advisor.com/Aspaki). They have revised their website and the pictures are not as good as before. Our suite/villa had a balcony/terrace from which we could see both ends of the island as well as the volcano and caldera, and the wonderful sunset. Can't wait to stay there again. We never left Oia - hardly wanted to leave our suite and terrace.

JUlie, Matt Barrett's site is easy to navigate but he's become known for being tied to certain places & services (perhaps for a percentage). I prefer this site by a younger GREEK guy http://www.greek-islands.us/, lots of pix, good overview.

Yes late August is still High Season (in terms of hotel rates), but after 8/20, crowds lessen because Europeans schools open. Still, you should book ahead. Most crowded are isles with huge charter planes of package-vacationers, and huuuge cruise ships dumping 3,000 people each into a port. This includes Mykonos & Santorini. The latter may be a "must-see" for a newbie; but you can easily do it as a day excursion from Naxos or Paros. OR visit it briefly en route elsewhere; it has good ferry links to the Western Cycladic chain. A 14-16 DAY CYCLADIC ITINERARY: Naxos (4) Santorini (2) Milos (4) Sifnos (4) Serifos (2) Or for more ideas, check my website; 2011 will be my TENTH GReece trip since 1999, to more than 20 islands & a dozen mainland spots http://www.techforecast.com/janet.htm

I have enjoyed all of the islands I have been on, but each does have it's own charm.

Mykonos: the town is famous, the beaches hedonistic and wonderful, the nightlife a party.

Naxos: Great variety, nice beaches, good solid vacation.

Koufonessia: Best beaches I have been on in the Mediterranian, virtually no tourism, but at least a few taverns and cheap rooms.

Santorini: Spectacular for the view, a must visit, get out of there after a couple days.

Crete: More a country in it's own right than an island. Too many things to sum up in a sentence.

We loved Santorini, but I'm not sure it's worth the cost. Expensive to get to, expensive food, expensive hotels (though we loved the Aris Caves). Fira was horrifyingly tourist, and I don't recommend going, but the walk from Fira to Oia was pretty great. Definitely stay in Oia!

loved Santorini because it was so pretty and lots to do. ruins, beaches, shopping, sunsets, great food. Symi harbor was probably the prettiest one we saw. Nisyros was really interesting with all the terracing and the thermal areas. Rhodes was fun as well. ruins, old town, beaches, again shopping and food. really enjoyed Mykonos as well.
we spent 14 days island hopping on a sail boat in 2008. visited 10. some only for an afternoon and evening, others for a couple days.

From one bay area girl to another We did a greek island cruise this past october. Had a stop in corfu and did a private taxi tour with corfuprivatetaxitours.gr Loved the tour and the beauty of the island, even though it rained. Would love to go back and spend a few days there. Dimitri runs the taxi service and we had an excellent ride to see as much as we could. Another stop was Iraklion on Crete. Once you get out of the busy town and port, it was country. Lots of vineyards and olive groves. Did some wine tasting and saw pottery being made. I would spend more time on the island. Heard that Chania is a pretty happening place but too far away to travel with a short time in port. Also fell in love with Mykonos. So as you can tell loved the greek islands i did see and would love to go and spend more time. Whatever you decide, go have fun; (eating, drinking and being merry.) the people were fabulous and so was the food. ENJOY
miss pupule

Chania in Crete is a great place to do all the things you described. The only negative about the town itself is a severe lack of parking if you decide to rent a car. Also, late August/early September is a great time to come here. The weather's very nice and it's the end of the tourist season, not quite as crowded as July or early August.

Bradley, in July & Early august, it's hard to find a parking place anywhere on any greek island!! Luckily for N. Americans, the European kids have to go back to school in late august, so the crowd thins out. By that time, there should be ample parking at that seaside parking area by the Western Wall in Chania. And if they're staying in Chania, no need to rent a car until they are leaving, anyway.

Yeah I guess I don't go down there on weekdays at all, I was thinking at night on weekends. Anyway, that time of year really is perfect to come here. I live in Kalathas which is a really small and quiet town with a decent beach, but still only a 15 euro cab ride to downtown Chania if that's your thing. That late in the year it shouldn't be a problem finding accommodation anywhere though.