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Jack & Jenny - Experience Conceptual Sailing

Cyclades Prefecture

With sailing weeks in the Aegean and Ionian Seas, Jack & Jenny offers something more than your average sailing week. The sailors that step on board discover a holistic experience of adventure, fun and relaxation.

The diversely themed sailing trips available at are carefully designed and filled with breathtaking sceneries and activities that promise to be exceptionally memorable.

But who are Jack and Jenny?
The two names represent a quest for the tailor-made adventure, combining a great route with unique experiences. Jack derives from the nautical slang and stands for “the seaman”, whereas Jenny owes her roots to the front-sail of sailing boats, the "genoa". The company embarked for its virgin trip in 2016, when a group of friends -all sailors- decided to turn their passion into a profession. Filippos, Stelios, Antonis and Jenny stood against the multi-dimensional crisis and started the first conceptual sailing company in Greece. Aiming to challenge the tourism sector and bring it to the next level, their mission is to share the Greece they know under a different view.

Whether you dream of majestic nights under the stars on secluded beaches, discovering ancient sites and hidden paradises, diving in crystal azure waters, partying till dawn, or are just looking for replenishment and relaxation, one thing is certain, Jack & Jenny has a sailing concept tailored for your taste.

Here are some of the concepts on offer:

  • Mad Dash will sail you away from busy harbors and into the most remote coves of the Cycladic islands while you learn about harnessing the wind's powers and trimming the sails for maximum performance.
  • A Dash of Time plots a course through the birthplace of Western Civilization where you can sail like an ancient mariner from one Antiquity landmark to another and wander amongst the ruins of myths and legends.
  • Mountain Dash seeks to fulfil the needs of the ever-restless adrenaline seekers, where sailing is combined with activities like canyoning, scuba-diving and cycling on the greenest coast of Greece.
  • Tranquilo aims to cover the wishes of the traveler who craves remote beaches but also wants to visit busy quaint harbors, wake up early to catch the morning breeze or party under the moonlight.
  • With Zen Week you can explore the practice of yoga while experiencing the purity of sailing with a daily practice among the natural elements on sandy beaches.
  • Vertical week is all about sailing and conquering precipice in the extraordinary climbing haven of Kalymnos and Telendos. 

What is at the core of Jack & Jenny is their trip-planning process.
As they say: "We love the process of designing our trips down to the very last detail. Creating a conceptual sailing experience and realising it while bringing people together and creating unforgettable memories is something we are really proud of!" 

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