How to Plan a Trip to the Greek Islands

I fell in love with Greece when my wife and I eloped in Santorini in June 2016. Santorini was the final island we visited after Paros and Crete. The next summer, we returned to the Aegean to visit three new islands: Hydra, Folegandros, and Milos. In 2018 we returned for another anniversary trip, this time visiting two new islands, Rhodes and Symi. Now it's tradition. We're going back for the fourth year in a row, to explore the Ionian island of Corfu.

Each of these trips has been 9-10 days in length. To plan them, I scoured guidebooks, maps, and blogs. I even deciphered descriptions of the islands in poetry and literature. Here are some tips for anyone considering a trip to Greece.

1. Stick to one island group

Just because islands look close to each other on a map, does not mean they are easy to get to. It's best to choose one family of islands and stick to it. Otherwise you'll waste all your time on ferries.

2. Fly directly to/from the islands.

Many islands have airports. You don't necessary have to stop in Athens to get to them, or to get home. I always try to get to the islands in no more than two flights. And I live in Seattle. So I usually fly to a major hub in Europe (Frankfurt, London, Paris, Dublin) and then find connecting flights directly to/from a given island.

A few examples:

Heading home after our wedding in Santorini, we flew nonstop to Frankfurt on Aegean Air, then nonstop from Frankfurt to Seattle on Lufthansa.

Last summer, to get to Greece, we flew Norwegian to London Gatwick, then direct from London to Rhodes on British Airways.

This summer, we're going to Corfu; we found a nonstop flight from Seattle to Dublin on Aer Lingus, and another direct flight on Aer Lingus from Dublin to Corfu.

3. Order islands strategically.

Try to arrange islands so that you start and finish on islands with airports. That will at least give you the option to avoid an extra flight (to Athens). Check out Olympic Air and Aegean Air for the shorter connecting flights in and out of Greece.

Something very important to remember: Ferries don't run every day. Some ferry routes run only twice per week, even in peak season. This means that when ordering islands on your itinerary you're at the mercy of the ferry schedule. It's best to start with a rough idea of how you want to arrange islands, but not to lock anything down (or book accommodation) until you're sure the ferries and flights align.

4. Use ferries sparingly.

I personally love the ferries in Greece. You get a different perspective of the islands when you approach ports from the water. But they can take a while. Since there are no direct flights between the islands (they all route you back to Athens first), ferries make sense (most of the time) for transport between islands. Just be realistic about how much time the ferry ride will eat up--usually a full day when you factor in rental car pick-ups/returns, embarking/disembarking, and inevitable delays.

5. Buy ferry tickets in advance.

I've never seen a ferry sell out, but it can happen. If your whole itinerary hinges on catching one ferry, save yourself the stress (and time) of buying tickets at the kiosk on the morning of your departure.

Choosing Islands

There are six main groups of islands. The Cyclades are in the middle of the Aegean sea. The Dodecanese are the easternmost islands near Turkey. The North Aegean islands are (shocker) in the North Aegean. The Saronic islands are below Athens along the Peloponnese. The Ionian islands are on the Western coast of Greece, with more Italian influence. Crete is usually listed separately, but could be combined with the Cyclades for trip-planning purposes. If you travel like I do, in 1-2 week bursts, three islands is perfect. Aim to spend 2-4 nights on each island.

Santorini is insane, but it gets mobbed in Summer. Still, you have to see it! I recommend staying in quieter Imerovigli rather than the more crowded Oia.

Naxos is one of the larger Cycladic islands, and apparently one of the greenest too. I've heard it's a great island for families.

Paros is the quintessential Cycladic island with the white sugar cube architecture. It's too sleepy for a lot of people. I thought it was sheer perfection.

There's also Antiparos. Tom Hanks has a house there.

Mykonos is known primarily for its nightlife. I've never been there, but I think its reputation speaks for itself.

Sifnos is rarely even mentioned in guidebooks. Avoid it unless you're trying to get off the grid, or write a novel, for a long chunk of time.

Ios is apparently even more of a party island than Mykonos. Popular with college kids.

Folegandros is tiny and barren but has spectacular cliffside views and a pretty town. Too solitary for my taste.

Syros is intriguing. The main town, Ermoupoli, is the capital of the Cyclades, more of a commercial hub but with some stunning architecture.

Andros and Tinos are larger but quieter, more traditional islands, great for walkers, with many traditional Greek villages, and a quieter atmosphere.

Crete almost feels like its own country. It boasts some incredible historical sites (Knossos, Phaestos...), stunning beaches (Elafonisi, Balos, Preveli...), stunning mountains and gorges, hundreds of charming, traditional towns, and the lingering influence of the Venetians, Turks, and countless other empires.

Rhodes has a rich history and is fun to explore by car.

Nearby Symi has the most beautiful port on earth.


Any questions? Leave a comment.



Leave a comment

Please note: comments must be approved before they are published.