Yacht sailing holidays & skippered tours in Greece
Discover more than 49 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
49
experiences
49
experiences
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
2 departures available
August - September
Starting from
€550
Per person
4.9
Super!
Greece: Ionian Islands
7 days - 7 nights
3 departures available
August - September
Starting from
€550
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
2 departures available
July - August
Starting from
€650
€618
Per person
4.7
Premium
Greece: Cyclades
6 days - 7 nights
One departure available
August
€2,947
€2,800
Per person
4.8
Greece: Ionian Islands
7 days - 7 nights
2 departures available
August - September
Starting from
€600
€540
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
August - September
€955
Per person
5.0
Super!
Greece: Cyclades
7 days - 7 nights
2 departures available
August - September
Starting from
€1,080
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
One departure available
August - September
Starting from
€585
€497
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
August
€990
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
August
€1,000
Per person
3.7
Greece: Ionian Islands
6 days - 6 nights
4 departures available
August - September
Starting from
€500
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
One departure available
August
€1,000
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
1777 reviews
Experience the sea at 360 degrees? embark with us in Kos
07/9/2025
Davide M.
-
Italy
Pack your suitcase and we'll take care of the rest!! Stewards on board!
07/7/2025
Diana U.
-
Italy
From the Dodecanese to the Cyclades: sailing off the beaten track!
07/7/2025
Farida B.
-
Italy
From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat
07/7/2025
Maddalena D.
-
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 & SupportLet's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964