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!
106
experiences
106
experiences
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
September - October
€950
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
October
€950
Per person
5.0
Super!
Greece: Dodecanese
8 days - 8 nights
One departure available
September
€650
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€790
€711
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€800
Per person
4.9
Super!
Greece: Ionian Islands
7 days - 7 nights
One departure available
September
€464
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
One departure available
August
€1,000
Per person
4.7
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
10 departures available
July - October
Starting from
€1,100
€1,045
Per person
3.7
Greece: Ionian Islands
6 days - 6 nights
11 departures available
July - September
Starting from
€500
Per person
Greece: Cyclades
5 days - 5 nights
2 departures available
August - September
Starting from
€900
€765
Per person
3.2
Greece: Sporades
11 days - 11 nights
One departure available
August
€2,226
Per person
4.9
Greece: Cyclades
13 days - 14 nights
One departure available
August
€2,050
Per person
Why book a holiday with Sailsquare?
The world's largest marketplace for sailing holidays
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
Find out more about the skipper and travellers who have already booked the holiday, to find out more about the
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
1767 reviews
From Rhodes to Kos: the fantastic South Dodecanese
07/1/2025
Patrizia F.
-
Italy
Pack your suitcase and we'll take care of the rest!! Stewards on board!
06/30/2025
Gilberto B.
-
Italy
From Rhodes to Kos: the fantastic South Dodecanese
06/30/2025
Silvia A.
-
Italy
From the Dodecanese to the Cyclades: sailing off the beaten track!
06/30/2025
elisabetta m.
-
Italy
Customer Support
Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!
Call us at
+44 2035144220Read our
Contact & Support
Can't find the perfect holiday for you?
Tell us what you are looking for and let our team find the right solution for you!
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
Let's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964
