Discover a week of sailing with
Sailing Weeks round the Greek IslandsSeven days of sailing to hidden splendours, surrounded by adventure seekers from all around the world.
Find your sailing week
Fresh out of the waterEvents and news from the Jack & Jenny team
Discover 5 secluded beaches while sailing with Jack & Jenny
Find out the 5 secluded and hidden beaches you will discover while Sailing with Jack & Jenny. Welcome Onboard!
Yacht Vacation in Greece: Why you should rent a yacht with a crew.
Yacht trip in Greece with a crew: Why is it your best option? Find out what each member of our team does to make your sailing endeavors with Jack & Jenny unforgetable
Yoga Yacht trip in Greece: This could be your best vacation ever.
Yoga Yacht Trip in Greece by Jack & Jenny. Combine Sailing and Yoga in a trip that will fill your mind and heart with the greatest memories.
Yacht trip in Greece: Cyclades
Planning a Yacht Trip in Cyclades, Greece? Find out the unique experiences that await you in the Aegean sea, and the Jack & Jenny sailing trips you can enjoy.
10 essentials for sailing in Greece
Ready for your Sailing Trip in Greece? Make sure your pack our ten essentials and enjoy your time onboard. Welcome to the crew!
Sailing in Greece COVID-19 free with Jack & Jenny
We at Jack & Jenny, don’t take your health lightly. Find out all the measures taken in order to ensure your safety while you sail with us, during the summer of 2020 and the corona virus outbreak.
Experience conceptual sailing in Greece with Jack & Jenny
Conceptual Sailing in Greece by Jack & Jenny. How do you want to experience your vacation? Choose your trip and sail to tell the story.
Jack & Jenny in the press
#sailwithjackjennyGet a taste of the experience
Filippos Kouzelis Mad Dash, 2016
No matter the weather, the comfortable and well-equipped boat and the crew gave us a feeling of security that allowed us just to enjoy the unique mindfulness and harmony that the nature around offered us. Thanks a lot for this unforgettable experience!
Anna-Christina Dembek Vertical, 2016
The week gets two thumbs up. The price in the end, the boat, the people, the islands, the skipper, the cruise, the climbing spots, the planning, the evenings... it was fantastic. It makes sense to combine climbers who are in the same level.
Dalia Bagdziunaite Tranquilo, 2017
This is a truly magical experience: dolphins, sunrise, rainbows and a full of love unicorn team!!!
Leonard Matter Vertical, 2016
It was an amazing week and I often remember it! really relaxed! as a testimonial i would suggest "Best Holiday for Geilons". Or maybe a stamp "Geilon proofed". Cheers & happy climbing!
Coraly Piccini Mad Dash, 2017
Crazily awesome, skipper outstanding, skipper’s partner was the kindest ever, the trip was amazingly inspiring, entertaining, delighting, adventurous, best memories ever!!
Harry Lampiris Mad Dash, 2016
Adding the wind, the sun and the sails in the mix of some of the most unique island landscapes, made my experience of visiting the Cyclades whole.
Lena Rennerich Mad Dash, 2016
We had an amazing time with "Jack & Jenny" in the summer of 2016 that we can highly recommend!
We have seen beautiful and wild coasts of many cycladic islands, were sleeping under the stars, swimming and snorkelling in amazing colored water and had a lot of fun with the crew.
Sea, sun, smiles and adventure, all in one!
Let's explore the Greek islands with best crew ever!
Ho ho ho and a bottle of rum! You guys rock!!
Jack&Jenny is all you need! Love you thank you, miss you always.