Off the beaten tack

Our cruises are about using the wind to explore the Greek Islands as no other tour does. Just as our motto and name says: Off The Beaten Tack!

Our yachts

Cyclades 50.5

0 Cyclades 50.5

Ikaros is the perfect vessel to explore the Greek Islands in comfort and style

You will be sailing aboard a beautiful Beneteau Cyclades 50.5 yacht. Measuring in at just over 50 foot in length, there are 5 double cabins with 3 toilets and 4 showers. On-board luxuries include full Air Conditioning in all cabins and entertainment features including PC with WI-FI, TV, DVD and CD player. From our experience though, you may want sound track your adventure, but we doubt you'll be tuning in to the TV when you see the sights we have to show you!

  • Length: 15.40m
  • Type: Sailboat
  • Fits 10 guests
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Off the beaten tack

About Us

Jimmy, the skipper of Ikaros says "there is nothing in the world I enjoy doing more than skippering a yacht and sharing my love of sailing and the sea with others. I have a great passion for the sea and what I do, and I try to express that through the core values of Off The Beaten Tack".


We have extensive knowledge of the Greek Islands and its hidden bays, idyllic beaches and beautiful destinations and use this knowledge to take our guests to the places that suit them – as the wind takes us, so every day can be different from the last, with that sense of adventure in the air.


We have run specialised yoga and meditation weeks with qualified instructors as well as art weeks with local qualified art teachers. If you'd like to curate a specialist week, from yoga, art, a corporate getaway, sailing school, water sports or anything else, just let us know and we'll do everything we can to accommodate for your needs!

Our destinations


Jimmy made the trip. He was awesome and I can’t imagine it being what it was without him.

Rhonda from Australia Rhonda from Australia
on “Greek Islands Sailing Tour” cruise

“I was a guest that sailed from Santorini to Mykonos with Jimmy as our skipper. I went with two friends and wasn’t sure what to expect, however upon meeting the other guests and Jimmy, we all felt at ease.

Maddie from Australia Maddie from Australia
on “Greek Islands Sailing Tour” cruise

“Sailing the islands of Greece with Jimmy was the highlight of my European trip/ Coming from Australia, the experience was completely unique. I had never seen the ocean look so blue. Cruising the islands is a great way to see new culture, fantastic sights and places out of your imagination. But by doing it on a sailing tour, I think I experience it in a much more unique and personal way. Jimmy was fantastic with the locals and everyone on board. He is not only great to get along with, but he is so so caring. Always making sure everybody is okay, safe, and enjoying their trip. He doesn’t take over - he listens to ideas and makes the trip suitable to what you want to see. I think seeing the Greek islands on a sailing tour will always be one of my favourite experiences. As someone never experiencing the ocean, apart from paddling in the waves, sailing was a completely comfortable , exciting and unique experience for me. I will one day make it to sail with Jimmy again.

Julia from Australia Julia from Australia
on “Greek Islands Sailing Tour” cruise