How many Greek islands can I see in a week?

I consider myself a full-blooded Greek islander and sailing is my great passion. The Greek islands are my literal playground. I prefer to take my time to get to know one island at a time, usually over the course of a week. You’d be surprised how much there is to see, even on the tiniest specks. But it is possible to do more than one on a trip of course.

With dozens of islands in Greece to choose from, it’s tough to decide which to include in a trip – trust me, I know. Every year I wrack my brain and spend hours researching my next island adventure. I’ve lost count of the number of times my husband has asked, “Why did you book that island?!” But every single time, after we’ve come home, we always bask in that glow of having explored somewhere new and intriguing.

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How to travel around the Greek islands

While ferries are still the main mode of transport between the islands, these days it’s much quicker and easier to reach them via air. While not all of them have airports, you can usually fly into one of the larger islands with domestic carriers such as Aegean Airlines (check their handy low-fare calendar), Olympic Air or Sky Express and take a short ferry to smaller isles nearby. If you do travel via ferry from port hubs Piraeus or Rafina, choose the fast ferry options, which cost a little more but get you there quickly. Ferryhopper is one of the best booking platforms, as you can map out your full inter-island journey.

My favorite mode of travel is (you guessed it) by sailboat. If you charter a yacht with a skipper, you can hop between islands at your pace – unless you or your companions possess a skipper’s license and have sufficient experience to captain a craft yourselves.

Planning your island-hopping getaway

May to October is prime time for the Greek islands, particularly if you want to soak up all the sunshine and swim in the glorious Aegean. Keep in mind that June through August can be hectic, particularly on the most popular islands, and flights and accommodation are at their most expensive, too. And who wants to wait hours for that restaurant table?

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Start by thinking about what interests you and what you’re looking for. Beaches with all the amenities or hidden rocky coves? High-end restaurants or toes-in-the-sand tavernas? Ancient sites or late-night bars? Do you want to chill on one or two islands and see as much of them as you can? Or would you prefer to see multiple islands?

I suggest taming your ambitions, and focusing on one island group, visiting no more than two to three islands in total. If you’re sailing, you can certainly drop anchor at a different island each day.

Take your pick of Greek island jewels

Most first-timers choose the Cyclades, homing in on Santorini for its cliffs dripping with whitewashed cubic buildings, and Mykonos for its charismatic appeal. Once you’ve had your fill of Mykonos, take the ferry to nearby Tinos. This low-key island has quietly earned itself a reputation for exceptional farm-to-fork fare, hiking trails and boutique wineries.

If you’ve got kids in tow, you might prefer to fly or ferry your way to Naxos, where kids can safely swim in shallow waters amid golden sands or learn to windsurf. From there, couples desperately seeking serenity and umbrella-free beaches can board the hardy Express Skopelitis for the Small Cyclades isles of Schinoussa, Donousa, Iraklia or Koufonisia.

If verdant hillsides, turquoise seas and stark white pebble beaches sound dreamy, the Ionian Islands beckon. Fly into Corfu, where you can cool off at sandy beaches and stroll the emerald isle’s romantic, cobblestoned capital. From there, take a hydrofoil to the twin isles of Paxi (or Paxos), whose unpruned olive trees deliver delicately flavored olive oil. From Paxos, hire a motorboat and scoot over to Antipaxos to dive into translucent aquamarine waters.

Down south in the Dodecanese, fewer travelers venture beyond Rhodes and its medieval old town, where you can envision knights thundering down flagstoned alleyways and wander through the seaside village of Lindos. Yet a short flight away is remote Karpathos. In hillside Olympos, women still don lavish traditional costumes for special occasions and celebrate with all-night panegyria (feast days).

Mapping out a Greek-island getaway might seem daunting but rest assured that whichever destinations you decide on, you’re guaranteed to return home with memories that will linger for years to come.