Greece sailing holiday map and highlights

Islands are scattered off Greece’s coast like a shaken-up snow globe. They are bewilderingly numerous at first glance, but great fun for sailors.
At first it might seem hard to piece Greece together from its thousands of islands, but there are a few key areas that every sailor should know. First: the Ionian Islands, specifically Lefkas, where many beginner sailors find their feet on flotilla holidays. Next up: the stylish Cyclades. Most people know Santorini, but the lesser Cyclades are joyfully unspoilt, and perfect for scuba divers. Then there are the places where the sailing takes centre stage. Experienced sailors will love racing across the Saronic Gulf from Athens. Brace yourself for afternoon sailing in the Dodecanese, when the meltemi wind gets up across the Aegean, and will take you from Kalymnos to Kos.
1. Cycladic Islands
2. Dodecanese Islands
3. Ionian Islands
4. Lesser Cyclades
5. Saronic Islands
Cycladic Islands

1. Cycladic Islands

Sailing between the Cyclades is as good as sailing in Greece gets. There are over 200 Cycladic Islands, but some are more well-known than others. You may be familiar with Santorini and Mykonos, with their whitewashed windmills and bright blue domes. But what about Amorgos, where Luc Besson filmed Le Grand Bleu, or Poliegos, deserted except for its caprine residents – its name means ‘many goats’.
Dodecanese Islands

2. Dodecanese Islands

The closest islands to Turkey, the Dodecanese can be almost punishingly warm. Crusaders used to fight over these hot rocks, and the fruits of their struggles are several medieval castles – especially on Rhodes, which also has the famous, acropolis-topped town of Lindos. In Kalymnos your photos will come ready-framed by arching rock formations – the island is brilliant for climbing and sailing adventures, with over 80 crags ripe for the scaling.
Ionian Islands

3. Ionian Islands

Lefkada is a gateway to the Ionian Islands for many sailors and its large marina is a thicket of masts. From here it’s easy to hop to Kefalonia’s north coast. Greece’s sixth largest island is generally under-visited, despite being the setting for Louis de Berniere’s ‘Captain Corelli’s Mandolin’. Head north instead and you’ll find brilliant bareboating around Corfu and Paxos.
Lesser Cyclades

4. Lesser Cyclades

An island cluster within an island cluster – the Lesser Cyclades are a little constellation of islands off the coast of Naxos in the Cyclades. Pirates marauded here throughout the Middle Ages, rendering them almost empty. Today, just four of the 32 islands are inhabited and they’re very quiet. Cruising is exceptional here, and the diving is amazing.
Saronic Islands

5. Saronic Islands

The Saronic Gulf was the birthplace of modern-day bareboating and flotilla holidays in the seventies, when the Yacht Cruising Association launched its first cruise in the area. They’re the closest islands to Athens and include Aegina, pretty Poros, and arty Hydra, where Leonard Cohen lived in the sixties. It doesn’t take long to escape Athens and get into authentic Greek island living.

Our top Greece sailing Holiday

Luxury gulet cruise in the Aegean

Luxury gulet cruise in the Aegean

5 star services while cruising the Greek Islands in luxury

From £945 to £1185 8 days ex flights
Small group travel:
2020: 25 Apr, 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 20 Jun, 27 Jun, 4 Jul, 11 Jul, 18 Jul, 25 Jul, 1 Aug, 8 Aug, 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct
Travel Team
If you'd like to chat about Greece sailing or need help finding a holiday to suit you we're very happy to help.
Written by Eloise Barker
Photo credits: [Page banner: Alex Antoniadis] [Intro: _dChris] [Cycladic Islands: Kostas Limitsios] [Dodecanese Islands: Saffron Blaze] [Ionian Islands: Gary Bembridge] [Lesser Cyclades: Zde] [Saronic Islands: Barcex]
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