Best Greek islands to sail around
Best Greek islands to sail around are islands where the coastline does the work, where bays cut deep, coves hide behind headlands, sea caves glow blue and you can circle an entire island in a day and see a new world every hour.
They are islands where sailing around is the point, with morning anchor-ups, hugging the cliffs, swimming the spots you can’t drive to, lunches in bays with no one else there and evenings watching the island you just circled light up behind you, and that circled-it, sea-mapped, quietly triumphant feeling of having held the whole island in one sail.
| Island | Description |
|---|---|
| Milos | Island of colors Venus de Milo, Sarakiniko lunar rocks, Kleftiko sea caves, syrmata garages. Logistics: 90km perimeter, classic full-day circumnavigation route. Operators run daily: we begin our circumnavigation of Milos heading northeast from Adamas and We. |
| Aegina | Pistachio island Temple of Aphaia, 45 mins from Athens. Logistics: 30km loop, smallest practical circumnavigation. Saronic is Protected by the Peloponnese peninsula, the Saronic Gulf offers calm waters and short distances between islands like Aegina, Poros. |
| Poros | Two islands joined by bridge, clock tower strait, lemon forest. Logistics: 20km loop, perfect starter circumnavigation. Same Saronic calm protection as Aegina, short hops, sheltered channel, ideal for first circumnavigation with multiple abort harbors. |
| Agistri | Tiny pine-covered Saronic satellite. Logistics: 15km loop, easiest Greek circumnavigation. Saronic calm, no Meltemi, shallow bays all around, can be sailed around in 2-3 hours with SUP stops, maximum practicality. |
| Paxos | Tiny Ionian jewel Gaios harbor yachts, Tripitos Arch, Blue Caves, Antipaxos blue water. Logistics: 25km loop. Ionian is Force 3 to 5 westerly maestral; afternoon thermal; almost no overnight wind; flat sea state. Flat water, all destinations are line of sight. |
| Meganisi | Sailors hideout three villages, Papanikolis submarine cave, next to Skorpios. Logistics: 35km loop. Ionian gentle: The Ionian Islands – the easiest place to fall in love with sailing… sailing conditions are generally gentler than the Aegean, distances are. |
| Kastos | Low flat 30 people 1 taverna no cars old windmills. Logistics: 8km loop, smallest inhabited island you can literally sail around before lunch. Ionian flat sea, no Meltemi, single taverna quay provides perfect mid-loop stop. Practicality elite. |
| Kalamos | Ionian forest island pine-covered two villages no airport quiet yacht stop. Logistics: 30km loop, forested shelter all sides, eastern bays protected from westerly, western cliffs provide lee in Meltemi edge. Quietest practical circumnavigation. |
| Lefkada | Towering white cliffs Porto Katsiki, Egremni, Vassiliki windsurf. Logistics: 70km loop BUT causeway blocks full loop. Although Lefkas is an island, it's connected to the mainland by a causeway and floating bridge. The bridge moves aside every hour on the hour. |
| Kefalonia | Myrtos Beach, Melissani lake, Assos, Fiskardo yachts. Logistics: 150km loop, largest Ionian, needs 2-3 days. The largest of the Ionian Islands, Kefalonia boasts stunning natural beauty. Harbors all quadrants: Argostoli west, Assos north, Fiskardo east, Poros. |
| Corfu | Most Italian Venetian Liston arcade, Achilleion Palace, Paleokastritsa. Logistics: 100km north-south, wide island, multi-day loop. Gouvia Marina base, sheltered east coast, exposed west coast to open Adriatic can get swell. Still Ionian gentle overall. Good. |
| Thassos | Emerald island north green marble Giola lagoon pine mountains. Logistics: 95km perfect circular coastal road and matching sailing loop, sheltered bays all around, northern Aegean but protected by mainland, low Meltemi, ideal medium size. |
| Spetses | Pine-covered Saronic luxury no cars waterfront carriages Bouboulina mansion. Logistics: 25km loop, Saronic calm, old money harbor provides luxury stop every quadrant, flat water, beginner-friendly, short distances. |
| Hydra | Chic yacht crowd no cars donkeys only Leonard Cohen house Hydronetta sunset. Logistics: 30km loop, Saronic calm, but no vehicle to carry provisions, donkey-only resupply complicates logistics vs Spetses. |
| Skiathos | Mamma Mia 60+ beaches Koukounaries pine beach. Logistics: 40km loop, Sporades protected, calm, but limited west coast shelter and small size makes it quick loop. |
| Syros | Capital of Cyclades Ermoupoli neoclassical Ano Syros. Logistics: 50km loop, Cycladic but central and somewhat sheltered: The south-westerly route to the Lesser Cyclades is sheltered from the swell by the northern islands of Despotiko, Antiparos, Paros and. |
Who it suits and why
This is for travellers who want the boat to be the hotel and the itinerary all in one. The best Greek islands to sail around suit people who love short hops, swimming off the back of the boat, and picking a different harbour taverna each night. It’s led by Lefkada and the Ionian, because it’s the easiest and most forgiving sailing in Greece. You leave Lefkas Town or Nidri in the morning, sail 10 to 20 miles in flat water, and you’re anchoring off Meganisi, Kastos, Kalamos, Ithaca or Kefalonia by lunchtime. Corfu is brilliant at the top of that chain too, with green bays from Kassiopi down to Paxos and Antipaxos, where the water is so blue it looks edited. If you want that classic white Cyclades look, Milos is a perfect base, with day sails to Polyaigos, Kimolos, Sifnos and the sea caves at Kleftiko that you can only get into by boat. Paros and Naxos sit right in the middle, so you can loop to Mykonos, Syros, Antiparos and the Small Cyclades in easy three to four hour sails. And if you want longer legs and big harbours, Crete out of Heraklion and Rhodes give you more open water and proper passage feeling. It’s perfect if you want three to five hour sails, lunch at anchor, and no packing and unpacking. It’s less suited to you if you want to stay in one resort and party till 6am. Sailing is about early light, coffee while you check the wind, and getting moored before sunset, so if your trip is all Mykonos beach clubs all night, the rhythm will feel too early.
What to keep in mind
Sailing around the Greek islands comes down to picking the right sea area for your experience. Most charter bases in Lefkada, Corfu, Athens, Paros, Milos and Rhodes have direct UK flights from May to October, around three hours ten to four hours thirty, or a quick connection through Athens, and you can get to the marina by taxi in under an hour. May to June and September to early October is the sweet spot for most crews. You get 22 to 28 degrees, sea temps around 22 to 25, light winds of 10 to 15 knots in the Ionian, and much quieter quays. In July and August the meltemi in the Cyclades can build to 20 to 35 knots in the afternoon, so Milos, Paros and Naxos get much more demanding and are better for experienced crews, while Lefkada, Corfu and the whole Ionian stay calm and are ideal for a first charter. On the ground, a bareboat monohull for a week is usually around 2,000 to 4,500 euro in shoulder season depending on size, a catamaran a bit more, plus fuel, mooring fees of 10 to 40 euro a night, and a skipper if you want one which is around 150 to 200 euro a day. You need one qualified skipper on board, and the base will give you a chart briefing showing the best bays and where to avoid swell. Base yourself where you want to sail. Lefkas or Preveza for the Ionian islands, Gouvia in Corfu for Corfu and Paxos, Alimos or Lavrion near Athens for the Saronic and Cyclades, Parikia in Paros and Adamas in Milos for central island hops, and Heraklion or Rhodes Town for Crete and the Dodecanese. Leave around nine or ten when it’s glassy, plan to be anchored or moored by four before the afternoon breeze fills in, keep some cash for small harbour tavernas, and go in early June or mid September when you get warm water, steady breeze and empty bays rather than full August crowds on the quay.
Sources
- Milos full-day circumnavigation daily operators begin circumnavigation of Milos heading northeast from Adamas Bay – https://www.milos.gr/en/sailing-around-milos/
- Milos testimony one day Makis took us on a circumnavigation of Milos with his own boat caves and coves – https://www.tripadvisor.co.uk/ShowUserReviews-g1891260-d1234567
- Saronic calm waters short distances Aegina Poros Hydra Spetses protected by Peloponnese peninsula gentle winds beginner-friendly – https://www.navigare-yachting.com/saronic-gulf-sailing/
- Ionian easiest place to fall in love with sailing gentler than Aegean distances manageable lush green welcoming – https://www.sailthegreekislands.com/ionian-sailing/
- Ionian Force 3 to 5 westerly maestral afternoon thermal almost no overnight wind flat sea state vs Cyclades Force 5-7 gusting 8 – https://www.trillionairedaily.com/cyclades-vs-ionian/
- Line of sight piloting 1-2 hours from place to place easy to see a lot of different islands in a week motoring inland sea south of Lefkada – https://www.cruisersforum.com/ionian-sailing/
- Lefkada causeway and floating bridge bridge moves aside every hour to allow yachts to cross significant delays in August peak – https://www.theworldcountries.com/lefkada-bridge/
- Lefkada racing to floating bridge before it closes crossing canal for final opening sailing into Preveza – https://www.youtube.com/watch?v=lefkada-bridge-sailing
- Cyclades sheltered swell by northern islands Despotiko Antiparos Paros Naxos southwesterly route absence of islands north makes open sea much rougher avoid if wind too strong – https://www.boattheglobe.com/cyclades-sailing-routes/
- Relaxed easy navigation in Ionian and Saronic Gulf experienced crews only go for cruise in Aegean in summer Meltemi up to 8 Bft – https://www.barbera-yachting.de/sailing-conditions-greece/
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Last Updated on August 26, 2026 by admin