+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

Kalymnos Rhodes Dodecanese South on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,100

Per person - min 2 pax

4.9

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

Greece: Dodecanese

7 days - 7 nights

3 departures available

July - September

Starting from

€850

Per person - min 2 pax

4.9

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

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - August

Starting from

€1,000

Per person - min 2 pax

4.6

From Kos to Rhodes on my catamaran

Greece: Dodecanese

7 days - 7 nights

One departure available

August - September

€980

Per person

Relax among the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€650

Per person

4.6

From Samos to Kos sailing the North Aegean and the Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July - August

€1,300

€1,105

Per person

Daily trip around Symi island

Greece: Dodecanese

1 day - 0 nights

One departure available

July

€125

Per person

5.0

7 islands in VIP formula - only 4 guests on board

Greece: Dodecanese

9 days - 9 nights

2 departures available

September

€1,350

€1,215

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

194 reviews

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 !

From Rhodes to Kos: the fantastic South Dodecanese

06/30/2025

Silvia A.

Italy

Bellissima esperienza oltre ogni aspettativa. Lo skipper super disponibile e simpatico e i luoghi visitati di una bellezza autentica hanno reso questa vacanza ,insieme alle altre persone che erano con me , davvero indimenticabile ❤️ Grazie di cuore

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

06/30/2025

elisabetta m.

Italy

Andrea è un professionista, sempre pronto a renderti felice! Abbiamo visitato posti stupendi e in condizioni di vento e mare piuttosto impegnative, che solo un esperto marinaio poteva rendere cosi' piacevoli!

SECRET DODECANESE: Astypalea and Tylos with skipper and kitchen

10/1/2024

Luca Alfonso M.

Italy

Emanuel ed Annalisa a dir poco fantastici, persone veramente squisite Bravissimi Skipper e Favolosi cuochi vacanza fantastica ed indimenticabile

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