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

2 departures available

July - August

Starting from

€1,000

Per person - min 2 pax

4.9

Super!

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

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

4.9

Super!

From Samos to Kos 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

4.9

Super!

From Kos to Rhodes, the South Dodecanese 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

4.9

Super!

Dodecanese: Fast Sailing, Crystal Clear Seas and Gourmet Cuisine

Greece: Dodecanese

6 days - 7 nights

One departure available

July

€950

Per person

4.9

Super!

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

Greece: Dodecanese

7 days - 7 nights

2 departures available

June - July

€1,000

Per person - min 2 pax

5.0

Aegean Sea adventure sailing trip from Rhodos to Crete

Greece: Dodecanese

7 days - 7 nights

One departure available

June

€645

€581

Per person

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

Greece: Dodecanese

7 days - 7 nights

15 departures available

May - October

Starting from

€829

€746

Per person

4.4

Kos, Kalymnos, Patmos, Leros: sea, colors and jewels of the past

Greece: Dodecanese

6 days - 7 nights

One departure available

June

€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

€1,200

Per person

4.6

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

Greece: Dodecanese

7 days - 7 nights

4 departures available

August

€1,400

€1,260

Per person

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Reviews - Yacht sailing holidays & skippered tours in Dodecanese

216 reviews

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

10/22/2025

Douglas B.

United Kingdom

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.

France

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!

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

09/16/2025

Bruno P.

We had a great time aboard the Alizé! As the other passengers have already indicated, Fabio and Irene, thanks to their professionalism, their kindness, their attention to detail and also (this is important! :)) their delicious dishes, allowed us to enjoy a week of happy disconnection. They quickly understood what we liked (fishing, sailing, hiking and discovering the beautiful Greek islands) and adapted the program accordingly. For us, we didn't spend a week with two strangers, but with friends. See you next year!

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