Sailboat yacht sailing holidays & tours in Greece
Discover more than 78 opportunities to get on board a Sailboat adventure in Greece. A unique experience with a local skipper, starting at €350 a week.
78
experiences
78
experiences
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
6 departures available
August - October
Starting from
€550
Per person
4.9
Super!
Greece: Ionian Islands
7 days - 7 nights
10 departures available
July - October
Starting from
€550
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
6 departures available
July - November
Starting from
€650
€618
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
7 departures available
August - October
Starting from
€1,080
Per person
5.0
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
September
€750
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
5 departures available
July - October
Starting from
€585
€497
Per person
4.9
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
July
€880
Per person
4.8
Greece: Ionian Islands
7 days - 7 nights
5 departures available
July - September
Starting from
€600
€540
Per person
5.0
Super!
Greece: Ionian Islands
6 days - 7 nights
One departure available
July
€790
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€870
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
September
€1,050
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 - Sailboat yacht sailing holidays & tours in Greece
1662 reviews
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
07/14/2025
Claudia Z.
-
Italy
The alternative to the catamaran in the Sporades
07/14/2025
Pietro M.
-
Italy
Sailing and Hiking in the Cyclades
07/14/2025
Marco P.
-
Italy
The alternative to the catamaran in the Sporades
07/14/2025
Ginevra S.
-
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 & SupportGreece: the best travel ideas
Let's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964