+44

2035144220

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.

experiences

4.9

Super!

From Kos to Rhodes: the beautiful south Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€800

Per person

5.0

Super!

The enchantment of the sea: the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

2 departures available

September

Starting from

€650

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board from Kos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

September

€1,050

Per person

5.0

Super!

Treat yourself to an unforgettable holiday. Embark with us in Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

August

€1,000

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€880

€836

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Karpathos

Greece: Dodecanese

7 days - 6 nights

One departure available

September - October

€950

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board - Karpathos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

5.0

Super!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

Per person

5.0

Super!

Experience the sea at 360 degrees? embark with us in Kos

Greece: Dodecanese

7 days - 6 nights

2 departures available

July - September

Starting from

€850

€750

Per person

5.0

7 islands in VIP formula - only 4 guests on board

Greece: Dodecanese

8 days - 8 nights

One departure available

July

€1,350

Per person

4.6

Cruise in the Dodecanese and off the coast of Turkey on a 17m boat with chef

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

Indeciso sulla scelta di Vacanza da affrontare Gianfranco mi ha messo subito a mio agio, tanto che è stato difficile scendere dalla sua "[hidden]" l'ultimo giorno. Vacanza pazzesca con bagni in calette incontaminate spettacolari per non parlare dei ristoranti da lui consigliati ottimi. Gianfranco trovami una location dove si balla Boogie boogie per giugno 2026 .Grazie ancora e ci rivedremo presto

From the Dodecanese to the Cyclades: sailing off the beaten track!

07/7/2025

Farida B.

Italy

I 10 giorni in barca a vela sono stati bellissimi. Un’esperienza che mi ha riempito gli occhi e il cuore… non sarebbe stata tale se non avessi veleggiato in compagnia di bellissime persone con le quali si é creata una piacevole connessione. Ringrazio il “Super Skipper Andrea”, un professionista: competente, affidabile e generoso. Una vacanza che consiglio a chi ama il mare e la libertà!

From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat

07/7/2025

Maddalena D.

Italy

Una settimana bellissima, rigenerante e super positiva. Fabio e Irene ci hanno accolto su Àlisè e ci hanno fatto subito sentire a casa. La barca è bellissima, accogliente e spaziosa. Fabio è un ottimo skipper, molto disponibile e affidabile, mi sono sempre sentita al sicuro nonostante il maltemi non ci abbia mai mollato e a tratti è stato impegnativo. Irene è stata un’ottima co-skipper sia durante la navigazione che nella gestione dei pasti e della cambusa. Anche lei molto disponibile e attenta. Ottima esperienza. Grazie ancora

From Rhodes to Kos: the fantastic South Dodecanese

07/1/2025

Patrizia F.

Italy

Andare in barca con Alessio e Anna è stata una delizia , baie splendide , Alessio sempre molto attento a capire i posti dove fermarsi e come accontentare tutti nei limiti del possibile. Anna deliziosa e preziosa con la sua instancabile energia. Consiglio di provare !

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 2035144220

Read our

Contact & Support