Sailing the Greek islands: everything you need to know

by | 11 Jun 2024

So you’re thinking of sailing the Greek islands? Excellent choice. But with 6,000 islands scattered across the Greek seas, it’s hard to know where to begin. Luckily here’s everything you need to know about sailing in Greece, from when to go, where to add to your itinerary, and what to pack before you set sail.


What are the sailing islands in Greece?

When looking at sailing the Greek islands, you can start by figuring out what kind of journey you’d like. There are two main options: the Ionian Sea, which is ideal for beginners with its calm waters, mild winds and lush, tropical landscapes; or the Aegean Sea, an archipelago which offers stronger winds and more dramatic coastlines, better suited for seasoned sailors.  

The Ionian islands are located on the western coast of Greece, made up of Zakynthos, Ithaca, Corfu, Kefalonia, Lefkada, Paxi (or Paxos) and Kythira (among other smaller islands). These islands are known for their lush flora, beautiful beaches, and incredible natural formations like caves, waterfalls and, in some cases, mountains. Thanks to their close proximity to Italy, the Ionian islands also boast unique Venetian architecture with churches, fortresses and other historic monuments.

Sailing boat in Greece

The Aegean sea is home to the famous Cyclades in the southeast, perfect for island-hopping if you can brave the more tumultuous waters, though that’s not to say there aren’t calmer routes around this area of Greece. There are 220 Cyclades islands, though most of these are uninhabited. Among the most well-known are Naxos (the largest Cycladic island), Mykonos, Santorini, Milos, Paros (and Antiparos), Sifnos, Kythnos, and Ios. Compared to the verdant landscapes of the Ionian islands,the Cyclades are more arid and rocky, though many of the picturesque towns are made up of white and blue houses that travelers will recognize.

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What is the best month to sail in Greece?

The best time for sailing the Greek islands depends on what you prioritize, be it warmer weather or quieter towns. High season is summer, from June to late August when you can expect long sunny days, clear skies, and warm water temperatures that range from 23°C to 27°C (73°F to 81°F). Bookending the high season, in June or September you can also enjoy milder winds in the Aegean Sea. It’s important to note that summer is the busiest time for tourists, so popular destinations tend to become crowded. 

A Greek town and harbour with and island behind

Across the Cyclades and the Aegean Sea, the Meltemi winds bring a strong, dry wind with clear skies and warm temperatures. These winds are at their strongest in July and August, meaning the beaches and towns may be slightly more blustery, and creating challenging sailing conditions, but ones that experienced sailors will relish. 

Shoulder season in Greece runs from April to May and September to October, but these are still excellent times to take a sailing trip and are part of the official sailing season. Both experienced sailors and beginners will enjoy shoulder season, with its calm seas and clear waters making the perfect conditions for swimming and snorkeling. 


What to pack for a Greek island sailing trip

Your usual packing list will likely suffice for a sailing holiday, but there are a few extra things to think about before you step on board your boat. Many Greek islands only accept cash, so make sure you source that before you set sail. The usual items like a hat, sunglasses, and an extra towel for any beach trips are important. And don’t forget your swimsuit!

White building of a Greek town overlooking the sea

Laundry might be a little tricky on the boat, so bring multiple pairs of shorts, t-shirts, and other clothes you want to wear. When thinking about clothes, fabrics that dry quickly are ideal, such as linen and cotton. If you’re going to be sailing the boat, then deck shoes are important (ideally with a light sole so the deck doesn’t get scuffed). Don’t forget sunscreen and bug spray, and then just add the usual toiletries you’d bring on vacation – but don’t overpack, as boats aren’t usually the most spacious!

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A dry bag to keep electronics in is invaluable, particularly for when you’re taking a dinghy from your sailing boat to the shore. When packing everything, a duffle bag is much more space-efficient than a suitcase, so that once you’re unpacked it can simply be rolled up and stored away.

Wherever you go sailing in Greece, you’ll be sure to find some incredible views, try delicious Greek dishes in their home country, and meet some friendly locals. Kaló taksídi!

Jess is an experienced writer and editor, with 6 years' experience working within the whisky industry. Her work has taken her to Scotland and beyond, while her personal travel highlights include backpacking around Vietnam with her sister, trips to California, Madrid, and the Greek islands.