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!
45
experiences
4.8
Super!
Greece: Cyclades
6 days - 6 nights
One departure available
September
€600
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
One departure available
September
€600
Per person
5.0
Super!
Greece: Cyclades
6 days - 6 nights
2 departures available
September
Starting from
€1,000
€750
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September - October
€835
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€980
Per person
4.7
Greece: Ionian Islands
6 days - 7 nights
2 departures available
September - October
Starting from
€900
Per person
4.7
Greece: Ionian Islands
6 days - 7 nights
2 departures available
September - October
€600
€540
Per person
4.3
New
Greece: Saronic Islands and Athens area
7 days - 7 nights
One departure available
September - October
€890
Per person
4.9
Greece: Cyclades
7 days - 7 nights
3 departures available
October
Starting from
€950
Per person
4.4
Premium
Greece: Saronic Islands and Athens area
7 days - 7 nights
26 departures available
May - October
Starting from
€1,305
€1,044
Per person - min 2 pax
4.9
Greece: Sporades
6 days - 7 nights
2 departures available
September
Starting from
€750
Per person
4.0
Greece: Cyclades
7 days - 7 nights
One departure available
September
€1,290
€1,161
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
2110 reviews
Sporades Experience: Freedom, Turquoise Sea and Greek Magic
09/8/2026
Cecile G.
-
GB
Sporades Experience: Freedom, Turquoise Sea and Greek Magic
09/7/2026
Salvatore Giuseppe Antonio S.
-
IT
Ionian Escape – Sailing Week from Corfu – Paxos & Antipaxos
09/7/2026
Mita M.
-
DE
Sporades Experience: Freedom, Turquoise Sea and Greek Magic
09/7/2026
Max B.
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 20 3514 4220Read our
Contact & SupportCan'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!
Follow us on
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964
