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Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,290

€1,190

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

10 departures available

August - October

Starting from

€1,400

€1,120

Per person

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4.8

Super!

Premium

Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

8 departures available

August - October

Starting from

€2,500

€2,250

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

10 departures available

August - October

Starting from

€570

Per person

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4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€800

Per person

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4.8

Super!

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

6 departures available

August - November

Starting from

€1,000

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

12 departures available

August - November

Starting from

€700

€665

Per person

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4.8

Super!

Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

July - August

Starting from

€1,800

€1,440

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

Per person

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5.0

Super!

Ionian Greece aboard a Catamaran with Skipper/Chef

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,900

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

€585

€527

Per person

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Reviews - Yacht sailing holidays & skippered tours in Greece

1967 reviews

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/25/2026

francesca b.

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IT

Beautiful week, excellently organized and managed by Andrea!! We had a very good time!
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Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

07/25/2026

Matthias S.

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IT

From the moment we stepped aboard [hidden] Cat, Aga and Greg made us feel like welcomed friends rather than guests. Aga is so much more than an incredible cook—she is an exceptional host. She has a genuine talent for making everyone feel comfortable and cared for. She was endlessly patient, always checking that everyone was happy, explaining everything with a smile, and creating such a warm, relaxed atmosphere on board. Every meal she prepared was fresh, healthy, and absolutely delicious. We ate incredibly well all week! Every single ingredient is organic fresh and simply delicious 😋 Greg was equally fantastic. He was always positive, calm, and professional, giving us complete confidence from the moment we set sail. We trusted him completely and always felt safe, whether we were sailing between islands or spending the night anchored in peaceful, crystal-clear bays. One of the most magical parts of the trip was sleeping at anchor under the stars and waking up surrounded by the sea. Greg and Aga took us to stunning hidden islands and secluded coves that we never would have discovered on our own—beautiful, authentic places far from the usual tourist crowds. The catamaran itself was extremely comfortable, very well equipped, and impeccably maintained. We slept wonderfully every night and had everything we could possibly need on board. Greg and Aga are wonderful people, outstanding hosts, and they made this one of the best holidays we’ve ever had 🐬😍💙🧿

Catamaran week among the islands of Ionian Greece

07/24/2026

Francesco B.

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IT

Nico is an experienced guy, nice and very good at creating a group. The catamaran is well maintained but above all it has on board anything you may have forgotten at home or that has not found space in your suitcase If next year I choose the sea again as a summer holiday, I will definitely contact him!

The most spectacular islands of the Cyclades: from Athens to Milos

07/23/2026

Frank W.

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DE

The cruise holiday in the Cyclades aboard the beautiful sailing yacht Anemeliá with skipper Alessio was spectacular! A perfect mix of pristine bays, crystal-clear blue waters, charming islands, and sailing whenever the wind allowed. The food on board was excellent, and the company of the other guests made the experience even more enjoyable. We had so much fun! Alessio is an experienced, professional, and friendly skipper who made us feel safe, relaxed, and welcome throughout the trip. Thanks to him, this holiday became a memory that will last a lifetime. We highly recommend this experience to anyone looking for an authentic sailing holiday in the Greek islands.

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Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

Greece: departures by month

Other travel ideas

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