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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

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

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

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

4.9

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

Greece: Dodecanese

7 days - 7 nights

2 departures available

August - September

Starting from

€850

Per person - min 2 pax

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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

201 reviews

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

07/13/2025

Silvana M.

Italy

Just returned from a wonderful week on [hidden] sailing among the northern islands of the decadonneso. Gianfranco is a professional, empathetic, sunny and fun skipper as only a true Romagna can be. Gianfranco immediately created a great team spirit by taking into account the characteristics of each crew member and creating a serene and cohesive atmosphere. I highly recommend this holiday, super location, the boat is comfortable and well maintained and Gianfranco a guarantee for a free fun and safe holiday.

7 islands in VIP formula - only 4 guests on board

07/13/2025

Riccardo L.

Italy

A Commander. He knows more than the devil and it is a pleasure to learn and confront each other. Experience that I wish to everyone!

7 islands in VIP formula - only 4 guests on board

07/13/2025

Alessia G.

Judò is a commander who is attentive to both the crew and the boat😁. Generous and helpful in teaching. With him you travel safely. His wife Amel is a delightful and tenacious skipper helper, excellent cook and now friend not to be missed. The "Drink Team" 🤩 worked excellently, but the captain had the last word.

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

07/12/2025

Attilio A.

Italy

Excellent welcome, well-designed itinerary, excellent on-board cuisine.

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