Which Towns Should You Visit While Sailing in Greece?

Sail around charming coastal towns in Greece with the Culture Trip’s Sailing Trips.

While your fellow sailors follow the fleet to Santorini or Mykonos, break away and let the wind guide you to the island of Koufonisia. Technically, it’s three islands, but the main one – Ano Koufonisi – is where you’ll find the port town of Koufonisi. Only a few hundred people live on the island, but you won’t mind the limited number of shops and restaurants if you spend all day kitesurfing or diving off the rocky caves into Pori Bay.

Let’s hope you aren’t sailing alone to Nafplio. This port city on the mainland is one of the most romantic in the country. Walk hand-in-hand up nearly 1,000 steps to the Fortress of Palamidi, snapping a sweaty photo that’ll bring a smile to your face for years to come. The promenade is equally as lovely a stroll – minus the stairs – and is ideal for an evening of wine tasting and dancing your way down to the beach.

When you arrive at the near-desolate port of Mersini, you may feel you’re at the wrong Cyclades island. Rest assured that you’re simply discovering the unspoiled island of Schinoussa, where many-a-pirate has called a haven. You could search for buried booty in the Cave of Maniatis, although the true treasures are the island’s sandy beaches where crowds – whether tourists, pirates, or otherwise – are virtually nonexistent.

It’s the spirits, not the sirens, that’ll lure your ship off course and into the port of Plomari. Mention the island of Lesvos to any fan of the hard stuff and they’ll immediately insist that you visit the Ouzo Barbayanni Museum. This family-run ouzo distillery is one of the most popular in the country. Grab a few green and blue aphrodite bottles so you can have a tasting at sea.

Legend has it that Poseidon sat atop the island of Samothraki and watched the fall of Troy. While you may not see that historic site, you can definitely get an eyeful when you dock in Kamariotissa. The beaches are as picturesque as ever, but it’s the interior of the island that will woo you. Load your day bag with cakes and bread from Salamanis Bakery hidden behind a yard of bushes and venture off into the wild mountainous forests. If you’ve only got time to dine and dash, our vote is for Fornello Pizza at Phorunelo and a fast – and cheap – visit to the Folklore Museum.

Let the wind guide your boat over to the butterfly-shaped island of Astypalaia and get your Santorini fix without the crowds. The whitewashed walls and blue doors of Chora are all the more dramatic atop its rocky perch. Here is where you’ll fill your camera roll – snapping countless photos of the windmills, churches and sunsets over the Aegean.

Yes, Piraeus is a major port of call – primarily serving the tourists marching to the Acropolis – but there’s more to this harbour than sailing down the typical tourist route. The bayside Archaeological Museum and Hellenic Maritime Museum will scratch your historical itch. Seafood is plentiful here – though it won’t come cheap, especially in Mikrolimano. You’ll soon forget how much the perfectly grilled sea bass set you back when you’re downing raki shots in the old red-light district of Trouba.

Don’t drop the sails just yet when you leave Athens – there’s still one more bit of history to explore in Katakolon. Secure the dock lines in this small town on the Ionian Sea and watch the cruise ships come and go – as your glasses of Mercouri wine do the same. A 34km (21mi) train ride to Olympia – the site of the first Olympic games – will reward you with a deep dive into ancient Greek history that will leave you planning another trip around Hellas.

Explore the coastal towns of Greece with Culture Trip’s Sailing Trips.