Experience conceptual sailing in Greece with Jack & Jenny

Greece is undoubtedly one of the most popular cruising grounds in the world. And for a good reason too. Crystal clear waters, untamed coasts, exceptional food, exquisite architecture and a cultural variety built upon millennia of history and traditions, set the scene for the eternal dance of wind, sun, and sea

The unique geography of the Greek Αrchipelago makes a sailing boat the ideal mode to explore the islands. At Jack & Jenny we believe that the best way to experience the Greek seas, is through our series of concept trips. Do you seek cultural cruises or adrenaline packed adventures? Are you fond of spiritual trips or scientific exploration? Our concept weeks aim to make your sailing holidays in Greece a personalised, one of a kind experience and a story that's worth telling.

Our concept trips have a duration of one or two weeks and each one will take you across a unique sailing route, complemented with carefully selected activities.  Each trip is an extraordinary, tailor made experience around the Greek islands. Choosing the concept best suited to your liking will set the ground for your next great getaway.

In search for adventure: a Sailing call of Nature

If it's a challenge you seek and the thought of popular tourist attractions turns you off, then Mad Dash is what you’ve been looking for. Sail away from busy harbours into remote coves and unspoilt waters. There you can fully experience the wild beauty of the Cycladic islands. But remember, solitude comes at a price and the hidden jewels of the Aegean do not give up their secrets easily. Battle with raging summer winds, choppy seas, and drop your anchor in waters, few dare go.

If you enjoy thin air, breathtaking views, and seek to stay active throughout your holiday, Mountain Dash offers it all. Sail across the Sporades islands, dive deep into the Aegean blue, and trek atop the iconic slopes and lush forests of Mt Pelion.  Wash the salt of your skin in natural pools and waterfalls. Through a series of guided activities such as Canyoning, Scuba Diving, and Cycling, embark on a journey to discover the lands where myths were born. 

“Aching muscles and raw fingertips - this is what it’s all about.”

The shorn cliff sides of Kalymnos and Telendos, are a welcoming sight only to those who have enough experience to traverse them. 

Vertical will sail you across the Dodecanese, where you’ll embark on a journey with over two thousand climbing routes. Grip the ledges tightly, for breathtaking views of neighbouring islands and unique landscapes will certainly set you off-balance. Every day  a different slope to conquer, every bay a new coast to settle.

Cyclades: A land of myth, a sea of history

Reading about history is one thing, however experiencing it first hand is another thing entirely. Experience A Dash of Time in a sailing week, that will take you through the immense history of the Cyclades. Sail your way from the bronze age to the Byzantine Empire. Dive into the myths and hidden history of the Aegean sea, explore the ancient ruins of the Greek islands, and swim amongst the legends of the past while history unfolds its cryptic puzzles.

For the easy-going: Set your own pace, Sail your own way.

Do you find yourself split between towns bursting with life, and secluded cozy coves where sunsets are just shy of magical? Are you the type to wake up early to catch the morning breeze and party under the moonlight? Tranquilo offers you just that: care-free sailing, authentic villages, turquoise waters, and the hunt for exclusive beach parties. The Sporades cluster of islands is the perfect combination of serenity and party-life. Everything is within your grasp in this island-hopping experience. 

Time is relative. Especially in this part of Greece where the pace of time is not a fixed constant, but a matter of choice. In Lazy Dash the wind is our guide and we are its followers. We let the mood on-board plan our journey, escaping the confines of tight itineraries.  So leave it all behind, put your watch away and sail along this timeless journey.

“A journey of the inner self, through the self, to the self.”

Zen, introspection, mindfulness. A journey that caters to your spiritual needs and love for yoga. Achieve your affirmations with the help of a certified Yoga instructor. Savour every moment with your journey companions, as you look for that which combines the sea with your search for plentitude. Practice yoga on remote sandy beaches and meditate in secluded coves as the sun sinks into the endless blue.

Do you perceive earth as a tiny speck of dust dotting the endless veil of the cosmos? Do the stars tell you tales of magnificent creation, and violent destruction? 

Follow the darkness with Star Dash and sail through the canvas of the universe. Our trained astronomer and his trusty telescope will take you to a star gazing journey of science and discovery in the most remote and isolated coves of the Aegean. Sail during the day and explore the stars during the evening. A journey through science awaits all the star lovers.

The deep blue - an endless and restless escape. Answer the call of the sea, dive into the unknown, and embrace  your Inner Blue.  A sailing journey where the surface of the sea is just the beginning. The wonders above and the secrets below the Greek sea await to be discovered. Follow our certified instructor through a series of dives for experienced and novice divers alike. Discover the underwater life, explore uncharted depths and experience the silent world which used to be our home.

Do you dream of majestic nights under the stars? The secluded beaches in the Greek seas? Discovering ancient sites, diving into the endless blue, or just relaxing and enjoying the sea? Jack & Jenny has a sailing concept tailored to your tastes

Make  your choice, embark on a unique adventure, and sail to tell the story.