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.
Our Greece sailing Holidays
Luxury gulet cruise in the Aegean
5 star services while cruising the Greek Islands in luxury
From
£1035 to £1359
8 days
ex flights
Liveaboard diving and sailing holiday in Greece
Combine a sailing and diving adventure in the Greek islands
From
£677 to £788
7 days
ex flights
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From
£1189 to £1324
8 days
ex flights
Cyclades sailing & walking holiday in Greece
Combine a sailing & hiking adventure around the Cyclades
From
£685 to £759
7 days
ex flights
Yoga and sailing retreat in Greece
-A week of relaxation and yoga while sailing the Ionian sea!
From
£850 to £900
7 days
ex flights
Sailing and cycling Cyclades holiday, Greece
Self guided or guided (upon request) tour in the Cyclades
From
€1500
8 days
ex flights
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From
£1189 to £1279
8 days
ex flights
Sailing and walking holiday in Greek Islands
Explore mainland hikes and secret Greek Ionian beaches
From
£1170
7 days
ex flights
Family sailing holiday in the Cyclades, Greece
Enjoy the beauty of the Greek islands
From
£1127 to £1313
8 days
inc UK flights
Cyclades Islands sailing holiday, Greece
Swim in turquoise seas & explore ancient towns
From
£1548 to £1663
10 days
ex flights
Saronic Islands sailing holiday in Greece
Sail among the beautiful islands & ports of the Saronic Gulf
From
US $2995
7 days
ex flights
Greek Islands sailing holiday
Luxury sailing in the Greek islands, reliving mythical tales
From
€2300 to €2640
8 days
ex flights
Rhodes sailing holiday in Greece
Aegean sea island hopping and sailing school
From
€420 to €1850
8 days
ex flights
Cyclades sailing honeymoon, Greece
Enjoy a romantic honeymoon sailing in the Cyclades islands
From
£3440 to £5209
7 days
ex flights
Small group sailing holiday Greece
Luxury sailing in the Greek islands with mythical adventures
From
€2460
8 days
ex flights
Saronic Gulf small group sailing holiday in Greece
Spend a week navigating the idyllic waters of the Saronic Gulf
From
£1799 to £1999
8 days
ex flights
Cyclades islands sailing holidays in Greece
A fantastic sailing adventure in the Cyclades islands!
From
€1250 to €1415
8 days
ex flights
Saronic Gulf sailing holiday in Greece
An 8 day trip combines sailing & swimming in Greece
From
€1250 to €1320
8 days
ex flights
Freediving and sailing holiday in Greece
-sail, freedive and explore the Ionian Sea
From
£750
7 days
ex flights
Sailing holiday in the Aegean Sea
Unique sailing adventure off the beaten track in Greece
From
£510 to £620
7 days
ex flights
Greek Island cruising holiday
Discover a side of Greece riddled with myth and magic.
From
£3050 to £3965
9 days
ex flights
Sailing holiday in the Ionian Sea
An unforgettable sailing adventure
From
£520 to £635
7 days
ex flights
Greece family sailing holiday
Sailing adventure for families or friends in Greek islands
From
€3600 to €4950
7 days
ex flights
Saronic Greek Islands luxury cruise
Luxury sailing the Greek islands in the Saronic Gulf
From
€2100 to €2620
8 days
ex flights
Family sailing holiday in Greece
Private sailing with fun games, reliving mythical tales
From
€2300 to €2640
8 days
ex flights
Greek Islands bike and boat holiday
Cycle and sail around the Cyclades Greek Islands
From
£1650
8 days
ex flights
Gastronomy and sailing holiday in Greece
Explore the Greek islands and their gastronomy with a chef!
From
€900 to €950
7 days
ex flights
Greece sailing holiday in Ionian Sea
Sail, explore and experience the Ionian islands in Greece
From
€600 to €825
7 days
ex flights
Luxury sailing holiday in the Aegean
Luxury sailing the Greek islands along the Aegean Sea
From
€2340 to €2670
8 days
ex flights
Sailing & conservation holiday in Greece
A unique wildlife & sailing adventure
From
£683 to £759
7 days
ex flights
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
5 star services while cruising the Greek Islands in luxury
From
£1035 to £1359
8 days
ex flights
Small group travel:
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.
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More about Greece sailing
Greece’s sapphire waters are dotted with so many white sails that you’d be forgiven for thinking the colour combination inspired the Greek flag.
In Greece, family is everything. Don’t be afraid of confining your brood to a boat for a week, it might be one of the most memorable trips your kids ever have.
Don’t mess with a classic. Greece is the original bareboating destination and it might still be the best. Read our guide to bareboat holidays in Greece to discover more.
Flotilla sailing was invented in Greece, and it’s still the perfect place to ease yourself into sailing solo. It gives you the freedom of having your own boat, with very little of the responsibility. Learn how to book your next trip with our guide.
Combine the meditative mindfulness of scuba with the lulling lilt of a boat under sail. There are arguably no two sports which bring you more in touch with the elements; learn more about combining the two sports with our diving and sailing guide.
When you sail in Greece you become part of a community. It’s a community of tanned captains and crew, all very happy to give advice. We’ve asked experts and customers for their best tips for sailing in Greece.
Sailors care about their seas. When not engaged on holiday trips, some operators use their boats to help with beach clean-up and conservation projects. But we can always be better. Find out about responsible sailing in Greece with our guide to being a good tourist.
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