
Yacht sailing holidays & skippered tours in the Cyclades
Discover the treasures of the Aegean Sea - a collection of islands with their own unique charm, landscapes, and coastlines. The Cycladic Islands act as a brilliant destination to unwind, relax, and connect with some of the most stunning natural beauty. Explore the stunning Santorini, Mykonos, and Ios with a passionate, local skipper.
3
experiences

4.9
Super!
Greece: Cyclades
6 days - 7 nights
3 departures available
August
Starting from
€1,040
Per person

4.9
Greece: Cyclades
7 days - 7 nights
27 departures available
April - October
Starting from
€1,080
Per person

4.7
Greece: Cyclades
7 days - 7 nights
39 departures available
March - December
Starting from
€1,000
Per person
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Reviews - Yacht sailing holidays & skippered tours in the Cyclades
463 reviews
From Mykonos to Athens by sail, with skipper and on-board kitchen
10/7/2026
manuela c.
-
IT
Fast Sailing Experience between Authentic Islands and Good Food
10/1/2026
Alexandra C.
-
CA
Luxury catamaran cruise in the Cyclades
09/30/2026
Sofi B.
-
GB
Sailing and Hiking in the Cyclades
09/30/2026
François-Gérald R.
-
FR
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This island of Mykonos, a favourite holidaying spot, is recognised for the beauty of its hilly landscapes, sandy beaches, and picturesque Cycladic white country chapels. Where as, the crescent-shaped Santorini, or Thira, as it’s otherwise known, is in fact a group of islands in the southern Cyclades.
The volcanic complex of the Santorini Islands has crafted some of the most unique arrangements of rock and ocean - while sunset images from the famous Caldera have become synonymous with romance. Then there is the island of Ios, known as Nios by the locals, and considered by many as one of the most beautiful islands in the Cyclades. The Panayia Gremiótissa church that stands at the highest point of Ios offers a striking view over the town and out onto the open sea.
The best kept secrets of the Cyclades are the islands of Sifnos, Koufonisia, and Amorgos. Sifnos with its red bougainvillea that hugs the white of the buildings, as the gentle Meltemi breeze flows over the hills and onto coastline. Koufonisa is said to compete with the best of Greek islands on all fronts. The port of Koufonisa sits on the islands only village, here some of the most charming blue lagoons are being secluded. Amorgos rises dramatically from the Aegean, creating extremely unique landscapes, and is described by skippers as a charm that you most confront at least once in your life.
The Cyclades, which originates from the Greek word for ring or circle, is in fact made up of around 220 different islands. This variety in island, partnered with the Meltemi winds, make for some of the best conditions for a sailing holiday full of discovery and fun.
Cyclades: the best travel ideas
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