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.
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.
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.
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!
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!
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.
Which Greek island is for me?
You can’t see all the Greek islands – at least not in one trip, anyway. So how do you decide which island to visit? Depending on what you want, here’s what each island offers each type of traveler.
Mykonos
Picture-perfect Mykonos is one of the most famous Cyclades islands, known for its Venetian windmills, white houses, and vibrant nightlife. A range of exclusive beach clubs help this island come to life day to night, so even if you’re not looking to stay out late but want to find some great cocktails, food, and music, then you can make the most of Mykonos. Beyond the bars, Mykonos has some of the most stunning beaches in the Cyclades, with white sand and crystal-clear waters.
Paros
Often touted as a ‘mini-Mykonos’, Paros has so much to offer in its own right without comparison. The village of Naoussa is not only a picturesque fishing village, but the top spot for great cocktails and incredible food, and is likely where the Mykonos comparisons come in. You’ll want a car to hop between the beaches on Paros, with many secluded beaches to explore. Don’t overlook Parikia, a town filled with whitewashed houses, winding streets, cafes, and excellent shopping.
Naxos
You’re never short of incredible beaches among the Greek islands, but Naxos has some of the best, characterized by soft sand and shallow waters. Agios Georgios is the largest beach on the island, while Agios Prokopios is the closest beach to Naxos town, and was even rated as Greece’s third best beach and among Europe’s top ten. The towns are perfect for wandering through, and visiting the Temple of Apollo at sunset is a popular activity but one that’s worth doing.
Ios
Known as one of the party islands, Ios is particularly lively and popular among younger travelers – but it’s rich in history and architecture too. Ios is considered to be the burial place of the Ancient Greek poet Homer, so in between the sunset beach bars and sea swims it’s well worth visiting his, as well as the open-air theatre “Odysseas Elytis”.
Santorini
For panoramic Instagram-worthy views, Santorini is the island for you. You’ll catch some of the most stunning sunsets in Greece here, with Oia one of the most popular sunset spots in Santorini. Beyond the pictures, Santorini makes incredible wine with many vineyards offering tastings, while the more active travelers will want to walk along the caldera for more unparalleled views.
Milos
If you’re after some truly unique landscapes while still getting your beach time, head to Milos. This volcanic island combines the dreamy duo of beautiful beaches and picturesque villages, with a geological twist. Sunbathe among the moonscapes of Sarakiniko beach, and catch the sunest – some say the sunsets on Milos rival those on Santorini. Visit Plaka village for one of the best sunsets in the world, and a stunning example of traditional Cycladic architecture.
Paxos
Paxos is the place to explore some of the most striking caves in Greece. Many of the beaches on Paxos are only reachable by boat, so we’d recommend dedicating at least one da on the island to a boat trip – if not to visit the beaches, then definitely to visit the caves. You can swim through the cave arches and find small slices of coastline to make your base for the day. In the evenings, this is the perfect island to enjoy fresh seafood in a traditional Greek taverna. If you have time, head to the nearby smaller island Antipaxos for a day trip to find some truly secluded beaches.
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!
