I am going sailing in the Greek Islands

When it comes to bucket list destinations, sailing the Greek Islands has long been one of mine.  Greece is home to numerous beautiful islands and stunning beaches that are best discovered with a sailing boat. Imagine sailing to azure blue waters, swimming in deserted beaches and visiting some of the most picturesque Greek Islands, doesn’t that sound like paradise?

This summer I have decided to make my dream come true and in July I am going to join Jack & Jenny, a sailing company created by a group of friends passionate about sailing, on a week around the Aegean Sea.

Jack & Jenny offers concept sailing weeks around the Greek Islands. I am going to join the historical week called “A Dash of Τime” that combines sailing with the most important archaeological sites of the Aegean Sea. Other themed sailing trips on Jack & Jenny include a yoga week, a performance sailing week, a climbing week and a canyoning week among others. You can see all the sailing weeks here.


My sailing the Greek islands itinerary:

I am going to spend 7 days sailing around the Cyclades islands, swimming in secluded beaches and visiting archaeological sights.

First Day: Mykonos island

This cruise starts and ends in Mykonos island one of the most popular islands around the world famous for its nightlife and beautiful Chora.

Second Day: Delos island

Delos is a UNESCO world heritage site and is considered one of the most important archaeological sites in Greece. According to myth, it is the birthplace of god Apollo and goddess Artemis and was considered so sacred that no births and deaths were allowed on the island. The cruise includes a private tour by an English-speaking guide.  After the tour ends we will head towards the Despotiko island.

Archaeological site of Dilos 2-min

Third Day: Sifnos island

The day includes a tour of the island’s most important’s sights such as the Mycenean Acropolis of Agios Andreas, the fort of Kastro, the 18th Century monastery of Chrysopigi by a private English – speaking guide, swimming and then barbecue on a secluded beach at the end of the day.

the archaeological site of Agios Andreas in Sifnos

Fourth Day: Folegandros island

A day to discover the picturesque Chora of Folegandros and to swim in the crystal clear waters of the island.

Fifth Day: Santorini island

In Santorini, we will have the opportunity to do a tour around the island, taste the unique wines of Santorini in a winery and swim.

Sixth Day: Santorini island and Iraklia island

The day will start with a private tour of the archaeological site of Akrotiri, a Minoan Bronze Age settlement that was destroyed in the Theran eruption about 1627 BC and buried in volcanic ash. After the tour ends, we will set sails towards the island of Iraklia where we will have the opportunity to snorkel above a crashed WWII airplane.

The WW II airplane that crashed in Iraklia


Seventh Day: Rinia island

The first stop of the day will be Naxos island for a swim before heading to Rinia island, with its fantastic beaches and turquoise waters where we will also spend the night.


Eighth Day: Mykonos

The cruise ends in Mykonos at around 11:00 am.

I am super excited with this amazing itinerary as it will be the first time I will visit most of the islands.

Apart from the skipper, the sailing cruise includes a hostess that will be there to make your trip enjoyable, answer your questions and prepare all the meals.  The menu of the day includes breakfast, light lunch, and dinner.

Find the sailing week that interests you on Jack & Jenny and join me on board for an unbelievable holiday of sailing around the Greek Islands.


For more information visit:


Tel.: +30 210 36 44 999
Email:  [email protected]
Skype:  jackjenny.co


I was a guest of Jack & Jenny but as always opinions are my own.


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