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!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

4.6

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

Greece: Dodecanese

7 days - 7 nights

3 departures available

August

Starting from

€1,300

€1,170

Per person

2.0

Aegean dreams: sailing around Rhodes - hostess on board (half board)

Greece: Dodecanese

7 days - 7 nights

3 departures available

August - October

Starting from

€829

Per person

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Reviews - Yacht sailing holidays & skippered tours in Dodecanese

218 reviews

From Kos to Rhodes, the South Dodecanese on a magnificent 15-meter boat

07/26/2026

Jerome B.

A very nice week aboard [hidden]e with Fabio and Irène. an extraordinary discovery of the islands between Kos and Rhodes. If you are looking for a change of scenery with just beautiful places. Go ahead! Fabio is a good adviser and a good captain. note peculiar to the village NIkia on Nisyros. a postcard. And the island of Tylos. We will return to this boat for more adventures. Thank you Fabio and Irene!

The North Dodecanese from Samos on a magnificent 15-meter boat

07/16/2026

Francesca T.

What a great experience! Fabio and Irene welcome you in their beautiful boat, making you feel immediately at ease. Expert guides of the Greek islands, take you to the most fascinating bays and places. Fabio, a captain with long experience, always makes you feel safe; Irene is an ideal travel companion. A holiday suitable for everyone, even those less used to sailing.

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

10/22/2025

Douglas B.

An extraordinary experience that exceeded all expectations

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

10/19/2025

Catherine S.

My first sailing experience was simply extraordinary! ⛵️ Unforgettable moments spent at sea, surrounded by incredible people. Anna Lisa and Emmanuel were amazing hosts! Thank you to everyone for your good humor, your kindness and this unique adventure. Can't wait to do it again! 🌊✨

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