7 Reasons to Go on a Greek Sailing Tour With Jack & Jenny

Back in July 2017, I did a sailing tour in the Cyclades with Jack & Jenny, a company that offers conceptual sailing trips in and around the Aegean Sea. I selected the historical-based A Dash of Time trip, which centred on the many archaeological sites in the Cyclades, such as Delos Island, a UNESCO World Heritage Site, Sifnos, and Santorini. 

It was my first experience on many of the islands and I really enjoyed the relaxed way of exploring. If you are thinking about visiting the Greek Islands, there is no better way to see them than by sailboat. Here are my seven reasons for joining a Greek sailing tour with Jack & Jenny.

ready to sail

Variety of islands you see

There are thousands of Greek islands in the Aegean Sea. Some are mere rocks, while others like Crete are large and inhabited. It would be impossible to visit all of them in a week, but with Jack & Jenny you get to experience a wide variety of the islands, depending on the cruise you choose.

Visit a lot of archaeological sites

There are many archaeological sites on the Greek Islands, from vast temple complexes to roadside relics of an era gone by. The historical week concept visits not just Delos, but also the archaeological site of Akrotiri in Santorini and the Mycenean Acropolis of Agios Andreas, the fort of Kastro, and the 18th Century monastery of Chrysopigi in Sifnos. It’s a compact history of the once-vast Greek Empire!

at the archaeological site of Delos

Experience many beaches

It’s not all sailing and sightseeing; Jack & Jenny makes it a priority to visit secluded beaches for morning or afternoon swims. After all, you are in the Greek Islands! Some of these beaches are only accessible by boat – which makes them even better.

Check out: The best beaches on the Greek Islands.

We had all this beach for us!
The colour of the water is amazing!

Enjoy fresh Greek food

The food on board is prepared by the hostess. This being Greece, it’s fresh, light, and packed with flavour. From dakos to fresh fish to fluffy pastry pies, all ingredients are locally sourced and delicious. Cruises include three meals a day, all prepared at the time and based on your dietary requirements.

You might also like : The best food to try in Greece.

Yummy breakfast!
Lunch with a view!

See dolphins and sea turtles in their natural habitat

There is no better thrill than having dolphins surf your wake or bow ride as the boat skims across the surface of the water. These playful creatures are smart and curious, which makes them a delight to see in the wild. The same goes for the sea turtles, who can be spotted swimming along with the boat.

Learn the basics of sailing

Sailing is an ancient form of transportation, and out there among the remnants of ancient civilisation, you get to learn the basics of sailing from a professional crew. Trim the sails, set a course, or simply hold the wheel – it’s whatever you want to do. But watching the sails unfurl as you get underway or watching the boom swing across as the crew tacks is a sight to behold.

Sleep under the stars

Bedding is provided, as are beds, but there is always the chance to curl up on deck and sleep under the stars. Far from the lights of civilisation, you’ll see the Milky Way in all its glory, be able to pick out constellations, and even hone in on the North Star. Jack & Jenny suggest bringing a sleeping bag if you wish to sleep on deck or on the beach!

My sailing trip with Jack & Jenny was truly spectacular, and I enjoyed the week very much. Not only did I get to visit islands and archaeological sites, I also got to spend the week with new friends and a fun crew aboard a beautiful sailing boat. I definitely recommend them if this sounds like your ideal adventure!

Jack & Jenny offers a wide variety of trips. While I did the historical-focused week, A Dash of Time, they also offer Mad Dash, Tranquilo, Mountain Dash, Zen, and Vertical.

Mad Dash is an adventure week, where you’ll learn more about the basics of sailing and head out to some of the most remote parts of the sea. Explore secluded coves and empty beaches with this unique itinerary.

Tranquilo explores the two sides to the Greek Islands – the near-private beaches and hidden gems but also the busy port towns and the bustling tavernas. This is ideal for travellers seeking the best of both worlds.

Mountain Dash focuses on the active traveller. Jack & Jenny partners with a canyoning company for this trip to offer guests the chance to explore the lands of the Aegean. Pack your hiking boot for this one!

Zen is all about yoga. Yoga weeks onboard the yachts are slightly different to the rest of the itinerary. They focus on emptying your mind to truly reach the root of it all. Experience yoga onboard a rocking yacht or on a deserted island.

Vertical takes you to new heights. Partnering with a climbing company allows Jack & Jenny guests to experience the thrill of Kalymnos, an island near the Turkish coast. Here, the dramatic limestone caverns and vertical cliffs offer a unique way to see the Greek Islands.

For more information check: https://www.jack-jenny.com/

Check out a video from my experience and other adventures with Jack & Jenny!

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2 thoughts on “7 Reasons to Go on a Greek Sailing Tour With Jack & Jenny”

  1. Oh Chrysoula. What a great experience (even thought I know that you will remember this trip for other reasons as well!!!). I have never sailed and even though I am not a sea type I want to do it once in my life! Well done to the host and hostess for their quality offerings.


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