At one time, the Greek islands were the playground of the jet set, made famous by Jackie O and her international coterie. Now a cruise to the Greek islands is an itinerary that's open to anyone, with options ranging from large mainstream cruise ships to smaller sailing yachts.
Your first decision when picking a Greek island cruise is how big a ship you want to be on. Larger cruise ships, such as those operated by Royal Caribbean, Celebrity Cruises, Princess Cruises, Carnival, Holland America Line or Norwegian Cruise Line, will only call upon the higher-trafficked islands, such as Mykonos, Santorini or Crete. The smaller the ship, the more likely that you'll be able to see off-the-beaten path islands like Skiathos or Hydra. Keep in mind that tendering is the rule, not the exception, at all the islands.
The good thing about the Greek islands is that they deliver something for everyone. History-lovers will seek out ruins both ancient and from the Crusades of the Middle Ages. Shoppers will have a field day in the stores and galleries, and beach bums will be in heaven, as nearly every island has plenty of sandy spots, some ranking among the best in the world.
The season in the Greek islands runs from May to late October. While July and August are the most popular for cruise ships, keep in mind that temperatures can top 100 degrees. June and September are probably the best months, as the tourist crush isn't as thick and the climate is cooler. Another factor for wine-lovers: September is the grape harvest at Santorini's vineyards.
Almost every mainstream cruise line, both U.S. and European, has Eastern Mediterranean itineraries that stop at the larger Greek islands of Mykonos, Santorini and Crete. (For more, read Eastern Mediterranean Cruise Basics.)
To really get an in-depth vacation on the Greek islands, you'll want to book with a line that has smaller cruise ships that stop at some of the less-trafficked ports. Options include luxury lines Azamara, Windstar, SeaDream, Seabourn, Silversea and Star Clippers.
Two Greek cruise lines, Celestyal Cruises and Variety Cruises, offer itineraries that focus only on the islands. Celestyal, which has been seeing an influx of North American passengers, uses larger, more traditional cruise ships and normally spends more time than the mainstream lines at each island -- with full days and overnights in some ports.
Eastern Mediterranean: The larger Greek islands of Mykonos, Santorini and Crete are often part of longer itineraries that embark in Venice or Athens and end in Istanbul. Another popular cruise itinerary calls on the islands on the way to Israel. This is the most common way that cruisers experience the Greek islands.
Greece and Turkey: Many Greek island cruises include stops at Turkish port cities like Kusadasi (home of Ephesus) and Bodrum. In Turkey, this stretch of coastline is called the Turquoise Coast, and its ancient history is similar to what you'll find in Greece. A cruise that concentrates on Greece and Turkey often runs between Athens and Istanbul or runs round trip from Athens.
Greece Only: If you're looking for true immersion in the Greek islands, look to smaller ships that concentrate solely on hopping between them. On these cruises, you're likely to begin the day at one island for a swim or snorkel, head to another for a barbecue lunch and finish up with an overnight in one of the more happening ports to take advantage of the nightlife. These cruises usually sail round trip from Athens.
Santorini: The iconic photo of a whitewashed church with a blue dome, set against an equally blue sea, comes from the small town of Oia on Santorini. Oia also has shops, galleries and restaurants in its narrow, picturesque streets. The island's main town, Fira (where the cruise ships tender), also offers gorgeous views of the caldera, as well as the volcano that created the island's high cliffs. Bonus for oenophiles: Some of Greece's best wine comes from Santorini, and you can easily spend the day touring wineries.
Mykonos: This island has a reputation throughout the world as one of Europe's main beach party spots. But there's a lot to see in Mykonos, even if sun and fun aren't your thing. Photographers will plant themselves in front of the island's too-cute windmills, while shoppers will enjoy the twisty streets of Little Venice. Or take a daytrip to the island of Delos, a once-sacred spot throughout the ancient world, to see the ruins.
Crete (Heraklion): Crete has two cruise ports, Chania and Heraklion. Of the two, Heraklion is the more well known. There, you'll want to head straight for the Knossos Palace, one of the most important archaeological sites in the world, with ruins dating back 4,000 years. From Chania, you can take a wine and olive tour with a guide or visit the chapel of Agia Paraskevi, set atop a pagan cave.
Patmos: Closer to the Turkish coast than Greece, Patmos is best known as a Christian pilgrimage site, due to its mention in the Book of Revelations. The Apostle John purportedly received the Revelations on the island when he was in a cave, now called the Cave of the Apocalypse. There's an affiliated monastery called the Monastery of Saint John the Theologian; both are UNESCO World Heritage Sites. If religion isn't your thing, visit the historic town of Chora, with its white Byzantine buildings.
Rhodes: Also close to Turkey, Rhodes has one of the best preserved medieval towns in the world, with buildings that date back to Crusader times. Of course, the island is much older than that; a Colossus that once stood in Rhodes' harbor was deemed one of the Seven Wonders of the Ancient World; alas, it's long gone. Walk around Old Town, or take an excursion to Lindos, a historic monument with the Temple of Artemis that dates to the 4th century BC.
Skiathos: Make Skiathos your beach stop, as the island has more than 40 beaches along a small coast. Or you can tour Skiathos Town; the island's main city has houses with quaint Mediterranean-style roofs, bougainvillea-draped balconies and enough cute alleyways to get lost for an hour or two. Walk up to the clock tower for a sweeping view of the island.
Skopelos: Made famous by the movie "Mamma Mia!", Skopelos is the island paradise where Meryl Streep frolicked with her various suitors. A boat trip that takes you to places in the movie is the main thing to do; otherwise, you can simply go to the beach.
Syros: This island isn't known for any noteworthy ancient sites (though it is home to an original El Greco painting). What visitors will find here is a taste of authentic Greece -- from its quaint beach clubs and restaurants to the shops, which primarily sell goods handmade or manufactured in Greece. That's because the island is mostly visited by Greeks from other islands. For those who don't want to stray too far from the port, the city (Ermoupoli) is perfect for casual strolls, where you can soak up the unique architecture (more akin to the French Riviera or Italy's Amalfi Coast) while you dine and shop.
Hydra: The main village of Hydra is as cute as they come, and you can easily spend a few hours browsing through the shops and having lunch near the marina. If you'd like to take an easy dip in the Med without taking a water taxi to one of the island's pebble beaches, walk around the promenade and up the hill to Spilia, a beach bar that also has a swimming platform and nice views.
Kos: Another island that's close to the Turkish coast, Kos has an ancient archaeological site with ruins of temples, shrines and a gymnasium. Other options include visits to vineyards, the beach or the mountaintop towns of Zia, Asfediou and Logoudi.
Lesvos: The third-largest island in Greece, Lesvos is famous for its ouzo and olive oil, both of which are sold in the shops and tavernas of Molyvos, the main tourist town. Visit the Castle of Mithyma, a Byzantine castle that sits on the site of an original fortification once taken by Achilles during the Trojan Wars.
Lesbos: The birthplace of Sappho is occasionally a stop for some cruise lines, which bring passengers to Mytilini; the island is also a draw for LGBT charters. Lesbos has a medieval castle, beaches and ruins. In addition, there's a petrified forest in Eressos.
Limnos: At the mouth of the Dardanelles, Limnos (sometimes written as Lemnos) has always held military significance for whoever happened to be in charge at the time. In ancient times, it was considered the holy site for the god Hephaestus (Vulcan to the Romans), and it has several Greek archaeological sites. Going back even further, the site of Poliochni is considered to be the oldest Neolithic city in Europe, preceding Troy.
Paros: Within the same island group as Mykonos and Santorini, Paros has the same great beaches and whitewashed villages they do -- only without the crowds. The Church of Panagia Ekatontapiliani is one of the oldest Byzantine churches in Greece. It was established by the mother of Constantine the Great.
Prepare for the sun. Temperatures can rise to more than 100 degrees on the Greek islands at the height of summer. You'll want to protect yourself with plenty of sunscreen, a hat and lots of water. While it's tempting to dive into the Aegean Sea without sun protection, you don't want to ruin the rest of your trip.
Prepare for crowds. During the high season, the most popular islands can get jammed -- not just with cruise passengers, but with people on holiday from Greece and the rest of Europe. Bring your patience and an open mind.
Prepare to tender. As noted earlier, tendering is the rule and not the exception on the Greek islands. Also bear in mind that most small towns in Greece have cobblestoned streets, and even the more populated islands like Santorini and Mykonos are difficult for people with mobility issues.
Prepare for price fluctuations. While mostly prosperous, the Greek islands have been hit with a continuous series of tax increases. The prices that you see online when you plan your trip might not be what you find when you're actually on the islands.