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!
135
experiences
4.8
Super!
Greece: Ionian Islands
6 days - 7 nights
One departure available
August - September
€650
€585
Per person
5.0
Greece: Ionian Islands
6 days - 7 nights
2 departures available
July - August
Starting from
€1,900
Per person
New
Greece: Cyclades
7 days - 7 nights
2 departures available
July - August
€1,050
Per person
4.9
Greece: Cyclades
7 days - 7 nights
5 departures available
July - October
Starting from
€950
Per person
New
Greece: Cyclades
7 days - 7 nights
One departure available
June - July
€790
Per person
New
Greece: Ionian Islands
7 days - 7 nights
2 departures available
August
Starting from
€690
Per person
5.0
Greece: Ionian Islands
6 days - 6 nights
12 departures available
July - November
Starting from
€1,099
Per person
4.9
Greece: Ionian Islands
6 days - 7 nights
8 departures available
June - September
Starting from
€2,650
€1,988
Per person
New
Greece: Cyclades
7 days - 7 nights
2 departures available
August
€1,150
Per person
4.5
New
Greece: Saronic Islands and Athens area
7 days - 7 nights
7 departures available
June - November
Starting from
€585
€527
Per person
4.9
Greece: Ionian Islands
4 days - 3 nights
One departure available
August
€280
Per person
Greece: Ionian Islands
7 days - 7 nights
3 departures available
September - October
Starting from
€779
Per person
Why book a holiday with Sailsquare?
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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.
Get onboard solo, with your family or your friends
Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.
Find out before you book who's waiting for you on board
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Sailing holidays that suit all budgets
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
1929 reviews
From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen
06/24/2026
Cesare S.
-
IT
In the heart of the Cyclades, from Milos to Athens (Lavrio)
06/24/2026
Alessandro A.
-
IT
From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen
06/24/2026
Cristina B.
-
IT
Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays
06/23/2026
Abby N.
-
US
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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
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
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
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