Two of my friends wanted to go for an extended cruise to Greece this year, so I started doing some research for them (and for myself since I am planning to go next year). If I did not get seasick, I would consider the cruise option, but between the possibility of being queasy during the entire trip and my lust for beaches and tasting local Greek life, I decided to stick to a land based trip.
One of the best resources I have found is the Greek Travel website; I love it because it has details on each of the islands so you can tailor your trip to what you like (discos or dinner at a quiet taverna?) There are so many choices that it can be overwhelming, so once you have some idea of how long you want to explore Greece and what kind of vacation you would like (beach or town, museums or hiking), check out Thesaurus Travel. It is always best to go with a local travel agency when traveling to a foreign country, and Barbara at Thesaurus speaks (and writes) fluently in English! She is helping me plan my trip based on my requests for good food (a must!), good beaches, and local (quiet) life on the islands.
My friends decided to be less adventurous, not wanting to deal with renting a place, figuring out directions and learning some Greek, so they have opted for a cruise through the islands. In today's economy, many of the best cruises are discounting prices by 50% or more, especially for bookings right before departures. Since they want to go this August, I found them a few deals through Vacations To Go. The site has details on dress codes, tipping and cabins, so it is like having a one stop cruise discount specialist online. Since my friends are younger (mid 30's) they prefer a more intimate ship like Windstar's Wind Spirit with ocean view cabins for $1599 per person (68% discount) departing August 29, 2009. My friends are like me and love great food, so I also found them Silversea's Silver Whisper suite for $3497 (50% discount) or balcony for $4347 (50% discount) departing Sept 5, 2009 (Silversea was rated by Conde Nast readers as the top cruise ship for food). These discounts disappear quickly as departure dates approach, so if you are flexible enough to go in the next few weeks, take advantage of the savings as they try to fill up the remaining cabins. These ships will sail with or without you, so climb on board with a fatter wallet by booking within a month of your departure.
Doing the research today means that I will be happier with my vacation in Greece (even if it isn't tomorrow).