Who is Jack & Jenny?

The child of Poseidon and the offspring of Aiolos.
Jack is every inch a sailor. Jenny is the driving force of sails.

It's a love story

The sea and the wind deeply connects them. Together they can reach any desired destination. Following their internal compass they keep discovering hidden paradises all along the Greek islands.

Jack & Jenny concept Sailing Weeks are seven days of sailing to hidden splendours most landlubbers couldn’t get to.

Experiencing exclusive events and being completely surrounded by an equal balance of adventure-seeking guys and girls from all around the world.

Our karmic sea story

Like a four strand square sinnet,

our stories intertwined to bring the best out of everyone involved.
After years of experiencing the Greek Archipelago and organizing numerous sailing, climbing, diving and racing trips, the founders joined forces to share that passion with you.



Instigator of Jack & Jenny, Filippos is the Zen force you’d wish to have when sailing around the Greek seas! He can be found on a boat, underwater, in a tent, under a palm tree, under a rock or in a seashell. He answers to dolphins’ whistling.



Fearless of strong winds and deep waters, Stelios knows better than anyone that a smooth sea never made a skillful Sailor.
Despite being a master in finance, wind to him is what money is to life for landlubbers.


Pirate Sextant

Whether it's sailing to the mountains or dashing through the times, rest assured this MAD navigator will plan for you a journey you'll never forget!


Social Mermaid / Galley Cat

She will scratch, and she will hiss, and she will blow your taste buds in with her alimental productions. When she is not diving in the Abyss of social media that is.

Jack & Jenny is the result of combining the best elements that sailing and Greek islands have to offer. Either pure sailing or combining it with activities, we have realized that “sailing is all about people”. They are the ones bringing the trip to a whole new level and creating those everlasting moments that will keep you warm during the winter.

Greece is the perfect playground with its endless shades of blue
and seductive beaches ready to be explored.

Our partners

Nothing would be possible without them