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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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3.0

Aegean dreams: sailing around Rhodes - hostess on board (half board)

Greece: Dodecanese

7 days - 7 nights

2 departures available

October

Starting from

€829

Per person

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4.6

Cabin boarding in the Cyclades, Astypalea and Santorini, sailing 17m. with chef

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€1,400

Per person

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New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

4 departures available

August - October

Starting from

€1,785

€1,575

Per person

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New

Sailing week south of Lefkas

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€800

Per person

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New

Sailing week in the North of Lefkas

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€649

€552

Per person

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4.3

Saronic Islands: a week on a catamaran between bays and villages

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

August

€1,350

Per person

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New

Premium

All inclusive catamaran cruise on a Bali 4.2 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

4 departures available

August - October

Starting from

€2,060

Per person

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4.6

"Boutique" sailing holiday from Athens to Hidra, Spetses and other pearls

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September - October

€1,200

Per person

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Sailing weekend in Greece - Diapontie islands

Greece: Ionian Islands

3 days - 3 nights

One departure available

September

€358

Per person

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5.0

Discovering the Northern Ionian Islands

Greece: Ionian Islands

7 days - 7 nights

7 departures available

August - October

Starting from

€1,000

Per person

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4.3

Catamaran cruise in the Saronics: between history and crystal clear sea

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

August

€1,450

Per person

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4.3

New

Small Cyclades: secret bays, pure relaxation and dreamy sea

Greece: Cyclades

7 days - 7 nights

One departure available

August

€1,150

Per person

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Get onboard solo, with your family or your friends

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in Greece

2003 reviews

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Sailing among the Islands of Ulysses. Stewardess on board

08/8/2026

Francescu G.

-

FR

A very pleasant trip. Hansel and Éléonore are adorable, knew how to make us discover magnificent coves, listen to the passengers and take into account everyone's desires. We highly recommend!!

Catamaran week among the islands of Ionian Greece

08/7/2026

Kristina S.

-

DE

Nicolo is a wonderful person. He is a very experienced, passionate and thoughtful skipper who knows his sailing territory very well. He makes the crew feel like home on board. The boat is very comfortable and very well equipped. We saw the most beautiful spots in the Ionian Sea while spending lots of fun time with Nicolo and our lovely crew. Thank you for this amazing experience!

Sailing cruise in the Greek islands - The Saronic Islands

08/5/2026

Donatella M.

-

IT

The sea, the sun, the wind are nothing without a good captain and Periklis has proven to be one in all circumstances and above all human expectations.
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Whale watching cruise with WWF guide in the Corfu archipelago

08/3/2026

Carlo P.

-

NL

It was what I wanted

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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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