Experienced Captains

All of our trips include a friendly, experienced, English-speaking, Greek captain who will navigate the boat, and more importantly serve as a knowledgeable guide to the ins-and-outs of each island.

Local Experts

If you’d like, they can suggest unique stores, beaches, historical sites, restaurants, and bars that are usually known only to locals and frequent visitors.

Authentic Cuisine

We recommend dining with your captain occasionally, it’s a great way to learn more about Greece, the islands, and the captain too. On some of the smaller islands, the menus are only in Greek, so the captain can help translate and suggest the local specialties that you won’t want to miss.

Meet Our Captains



“The Skipper and his wife/hostess (Kosta and Mary) were simply the best. Kostas’ knowledge of sailing and the various islands was incredible”
– TommyTony11

Kostas began sailing at the young age of 14, but it was his dream since he was 9yrs old. At the age of 18 he attained his offshore sailing skippers license. A year later Kostas joined the Greek Merchant Navy Academy as a deck cadet, where he was trained in navigation, meteorology, safety issues and more.

Since 1999, Kostas has worked as a full time skipper, sailing thousands of miles a year in charter and deliveries in Greece, the Mediterranean and the Red Sea.  When you sail with him you’ll notice that he seemingly knows tons of people on every island and is able to make all kinds of arrangements for activities, dinners, excursions, etc.   He is known for his kind demeanor and his willingness to share with you the secrets and pleasure of yachting and the unmatched beauty of Greece. His favorite place to sail is Cyclades.



“It was truly one of the most brilliant weeks of our lives. Captain “K” was awesome.”
– jkjolly1

Kiriakos was born in the island of Ikaria. Because the island of Ikaria is surrounded by rough and high seas, many citizens were raised to be sailors. His father was a captain on cargo ships who often took Kiriakos on big trips around the world when he was a child..

He took to sailing at a very young age, soon started to captain sailing boats in races and charter trips. He has owned a boat for many years which has been one of his prize possessions.

His favorite island is the island from which he was born, Ikaria, but he loves the entire the Aegean. When the season is over, if he is not sailing in international waters, you will probably find him racing his own boat in a local regatta.


Yiannis A.

“Each island was amazing not in small part due to the advice, direction, and often the company of our captain (Yiannis!!!!!)”
– smhopps31

Yiannis was born on the beautiful island of Paros in the Cyclades.  He’s been sailing the Greek isles since he as far back as he can remember.  His impressive sailing ability is complemented by a laid back demeanor and friendly face, making him a perfect captain for charters.  He also prides himself on knowing the best restaurants, bars and beaches on many of the smaller Greek Islands.

Yiannis P 1

Yiannis P.

Yiannis P. is half-Athenian & half-Cretan and, as everyone is in Greece, is very proud of where he’s from.

He’s been sailing since he completed his military service – first with friends, in sailing races, and transferring yachts around Greece, and then as a charter sailing captain. While most refer to passengers as ‘customers’, he likes to think of them as ‘co-sailors’.

When he’s not sailing he enjoys playing music – he says both help keep your spirit free.

Explore our yachts & the amazing islands you'll visit
Our YachtsRoutes & Islands