Yacht sailing holidays & skippered tours in Dodecanese
Discover hundreds of sailing holidays in the Dodecanese Islands. Book a spot onboard and live a unique experience with a local skipper. Starting at €400 a week.
19
experiences
19
experiences
4.9
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
July
€800
Per person
5.0
Super!
Greece: Dodecanese
7 days - 7 nights
2 departures available
September
Starting from
€650
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
September
€1,050
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
August
€1,000
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
October
€950
Per person
4.9
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
July
€880
€836
Per person
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
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
2 departures available
July - September
Starting from
€850
€750
Per person
5.0
Greece: Dodecanese
8 days - 8 nights
One departure available
July
€1,350
Per person
4.6
Greece: Dodecanese
7 days - 7 nights
2 departures available
August
€1,600
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 Dodecanese
197 reviews
Experience the sea at 360 degrees? embark with us in Kos
07/9/2025
Davide M.
-
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
From Rhodes to Kos: the fantastic South Dodecanese
07/1/2025
Patrizia F.
-
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 & 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!
Dodecanese: the best travel ideas
Let's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964