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Jack & Jenny

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Athens, Greece
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About Jack & Jenny
Tailor-made sailing adventures in the hidden splendours of the Greek Seas. We offer multi-day sailing experiences starting from Athens, the Cyclades, Ionian & Dodecanese. Specializing in concept trips where we combine sailing with activities like climbing, diving, yoga or themes around gastronomy, history and astronomy.
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Overview
This Week is an ode to the freedom of smooth cruising under sail. The little Cyclades are a fantastic sailing ground with flat seas to sail and crystal clear turquoise waters to explore at a relax pace.

This week we begin our journey from the port of Paros and head south to the little Cyclades. The journey will first take us to the remote island of Despotiko to experience the Cycladic night Sky in one of our favourite remote beaches.

The next days are completely dedicated to the turquoise waters of Schoinousa, Ano Koufonisi, Keros and Kato Koufonisi. Swim and dive amongst in some of the most extraordinary beaches of the Aegean. We continue with a northbound upwind sail to Donousa, before we head west towards the islands of Macheres and the port of Naxos.

In Naxos you will get to walk between the narrow alleys of the Old Town, blend with the locals and experience the Cycladic night life.

Finally we will head back to Paros for our farewell.
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Sara Findlay wrote a review Jul 2022
1 contribution
+1
THE CAPTAIN - Tommy was nothing short of incredible! He knew the area, the towns, the oceans and the history. We felt safe and in good hands at all times. THE LOCATION - we sailed the Ionian Sea and it was beautiful. The beaches were white with amazing cliffs and turquoise waters. The harbours were quaint and had great food as well. THE BOAT - we sailed for the 7 days on the Casta Diva and she was an absolute treat - nothing was broken, the interior was chic and user friendly. I would recommend this to small families, groups of friends and even couples looking for a getaway!
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Date of experience: June 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Mias v wrote a review Jun 2022
Cape Town, South Africa4 contributions2 helpful votes
+1
We did a 7 day trip in the Ionian Islands with Jack and Jenny Sailing for my Dad’s 60th after having to delay for a few years due to covid. What an incredible experience! I have travelled Greece on land/scooter a couple of times before but nothing comes close to experiencing the beauty of Greece by boat. Our skipper Tommy was one of the highlights of the trip and his local knowledge of the area combined with his Greek passion and desire to ensure we have the best time possible provided us with an unforgettable curated experience that honestly blew my mind. This has left me desperate to start planning the next Sailing trip. ευχαριστώ Tommy hopefully you come visit us in South Africa some time.
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Date of experience: June 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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SJL1605 wrote a review Mar 2019
Tel Aviv330 contributions209 helpful votes
We had an amazing family vacation sailing with Jack & Jenny for the week. Firstly, the communication before the trip was great. They answered all of our (many) queries and did everything possible to make sure that the trip was planned to our satisfaction. The activities we did were all perfect and when we werent active we found time to be together as a family and relax on the boat. It was such a memorable trip for all of us and nothing was too much to ask. Would highly recommend Jack & Jenny for anyone looking to get out onto the water in the Greek Islands!
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Date of experience: August 2018
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Christina L wrote a review Mar 2019
5 contributions
+1
I was the one that organized our trip for the first time with Jack & Jenny. First of all, I was very happy with the quality of communication; pleasant and uncomplicated, they were able to arrange everything and set the mood. We started feeling the holiday vibes even before we take our plane to Athens. Second, I was of course concerned about whether my friends would like the trip I recommended them. Most of them were trying out sailing for the first time and were rather skeptical at first. However, after our first hour with our Captain -Stelio, and for the rest of the trip, I could only see happy expressions on their faces. We asked him to teach us a little bit about sailing and he actually did! haha. That was a first for all of us and we got pretty excited with this learning experience. Safety always came first and therefore we were able to rely on the captain and the crew, and there was no concern or fear during our practice or sailing in general. Captain Stelios demonstrated remarkable skills in handling a boat, handling a crew (us), and he was a great (and funny) company to us. He knows the seas, the winds and the islands like the palm of his hand and we were therefore able to discover places that we would have otherwise never come across- the authentic Greece. We all loved the whole experience and we are already arranging our next trip!! This time my friends are bringing more of their friends along too, haha. I guess their excitement was too contagious. For this year Jack & Jenny arranged a new experience for us that seems to be even better than the previous one. New locations, new adventures planned and new impressions. That makes our holiday decisions and planning so easy again - we are looking forward to it! I would definitely recommend Jack & Jenny for all those reasons and more. Ahoy you future sailors!
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Date of experience: August 2018
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Birger wrote a review Mar 2019
5 contributions1 helpful vote
+1
Since I had no idea what to do for summer holidays that year, some friends of mine convinced me of having a sailing trip in the aegean sea (actually the first sailing trip of my life). What can I say; it was worth every second. I had an amazing time with my people and the young, sympathic, very professional and well prepared crew. My highlights were the food we had on the boat, sailing with dolphins, having a barbecue on the beach, snorkling in turquoise-blue water and generally travel around with the locals experiencing they know their sea inside out. We also learned some sailing which was very nice. I would recommend the mad dash-tour a 100%. Keep it going guys; looking forward to the next trip!
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Date of experience: August 2018
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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