Greece 9-Day Sailing Trips & Itineraries

Explore 3 sailing trips designed by local kimkim specialists to get ideas for your trip to Greece.

Who hasn’t dreamed of a sailing holiday around the iconic Greek isles? In nine days you could plan a comprehensive sailing tour that mixes history, culture, and adventure as you sail around the Aegean Sea, from the Temple of Poseidon to the double-bay beaches of Kolona. You could also opt for a luxury yacht cruise that visits such crowd-pleasing islands as Naxos, Mykonos, and Syros. Yet another option is to sail the Saronic Gulf, offshore from Athens, which is home to islands abounding in ancient ruins like Aegina and Poros.

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Mykonos harbor
Map of Luxury Cyclades Yacht Cruise - 9 Days
Luxury Cyclades Yacht Cruise - 9 Days

Cruise like a celebrity through the glittering waters of the Cyclades on this nine-day itinerary.  The Cyclades are some of the most quintessential Greek islands, and you'll see seven of them from the decks of your yacht, along with plenty of time to explore onshore. From lesser-known spots like beach-lined Milos and petite Antiparos to favorites like bustling Naxos and cosmopolitan Mykonos, you'll scope out this island chain in style.

Beach off of Milos
Map of Sailing Holiday in the Aegean - 9 Days
Sailing Holiday in the Aegean - 9 Days

Channel the spirit of some of Greece's most famous tales as you sail through the Aegean on this nine-day itinerary. Start off by paying the proper tribute at the Temple of Poseidon before you start on your way to Kea, followed by the villages of Kythnos. Visit the capital of the Cyclades on Syros and the home of the Cyclops on Serifos, then search for the Venus de Milo's cousin on Milos before you end your trip on the double beach of Kolona.

Boats off Moni island
Map of Sailing Holiday in the Saronic Gulf - 9 Days
Sailing Holiday in the Saronic Gulf - 9 Days

Spend nine days getting your sea legs with this sailing itinerary. Once believed to be one of six entrances to the Underworld, the Saronic Gulf is now one of the most popular yacht spots in Greece. You'll travel to a new island each day, taking in harbor towns and historic temples and churches, sampling island specialties, and enjoying the sea breeze.