Depending upon your specific definition of an island, Greece boasts around 2,000 islands, most of which are uninhabited. The islands essentially consist of clusters including: the Ionian Islands, located to the west of the mainland in the Ionian Sea; the Cyclades in the central part of the Aegean Sea; the North Aegean islands, off the west coast of Turkey; the Dodecanese, between Crete and Turkey; and the Ionian Islands, located west of the mainland, in the Ionian Sea.
When planning a cruise of the Greek Islands, be aware that many do not have ports, harbors and facilities large enough to accommodate the bigger cruise ships, that many travelers use because of their array of facilities and services. If you decide to take a cruise on a large ship, you may be waiting in long lines for transportation from ship to shore, and you'll have to pay additional charges to tour the most picturesque islands such as Santorini and Rhodes. You'll also find that small resorts are ill-equipped to cope with a massive influx of visitors, and historic sights, beaches, restaurants and shops will be crowded. While the brochure or website may say your cruise takes in Rhodes, for example, be aware that your ship will probably dock in nearby Marmaris, Turkey, where you can pay for an additional excursion to take you to Rhodes.
By embarking on a smaller ship cruise, you can visit destinations that aren't accessible to larger ships. With only 148 to 312 guests, depending on the ship, Windstar's luxurious and graceful multiple-masted yachts offer the opportunity to dock and visit islands including Milos, Mykonos, Rhodes and Santorini. The company was voted one of the top five in "Travel + Leisure" magazine's World's Best Small-Ship Cruise Lines for 2010.
If you can afford it or you have like-minded friends and family just as keen to cruise the Greek islands, it is possible to charter a yacht and crew and arrange a cruise that visits locations off the beaten cruise-ship path. If you are a proficient sailor, you could even rent a yacht to sail yourself. Check websites such as Poseidon Charters to get an idea of what is available and prices.