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 South Dodecanese on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€1,000

Per person - min 2 pax

4.9

Super!

Rhodes Kalymnos South Dodecanese on 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

Discover the most authentic Greece from Samos to Arki and Agathonisi, with skipper and chef

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€1,200

Per person

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

Greece: Dodecanese

7 days - 7 nights

4 departures available

July - October

Starting from

€829

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

€1,200

Per person

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

€1,400

Per person

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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

217 reviews

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! 🌊✨

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

10/19/2025

Olivier P.

Some sailings leave a softer trace than that of the boat's wake. The sailing week was perfect: beautiful sailing, delicious food and a friendly atmosphere. Thank you to them for this wonderful interlude — I will leave without hesitation!

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