Bearing True South - Guided Adventure Tours in Greece


One of the most famous archipelagos in the world, the Cyclades have way more to offer than pristine beaches, crystal clear waters and amazing sailing experiences. They are the cradle of over ten millennia of rich history, boast extreme geographical diversity, abundant marine wildlife and feature the best of traditional Aegean architecture and Mediterranean cuisine. This sailing adventure goes far beyond mere island hopping, giving you a chance to explore way beyond each island’s marina, as well as immerse in local culture, savor the local flavors and learn a thing or two about the history of this immensely beautiful part of the world. And did we mention that it provides you with the opportunity to actively engage yourself in sailing, whether you have done it before or not, The Aegean archipelago, with its clear deep blue waters is the ideal place to get acquainted with the basics of sailing and our skippers are always happy to show you the ropes!

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Trip Highlights

  • Immerse in the rich culture, delicious cuisine and millennia spanning history of Athens
  • Explore over a dozen different beautiful sailing destinations, visiting six islands in the process
  • Swim then hike to the Temple of Poseidon at Cape Sounion
  • Enjoy the laid back atmosphere on the quiet island of Kythnos
  • Relax in a hot spring while looking at the Milky Way at the tiny fishing village of Loutra
  • Savor amazing Aegean seafood on the island of Sifnos
  • See unique geological formations and swim in turquoise waters on the volcanic island of Milos
  • Swim in turquoise waters by the uninhabited tiny island of Polyaigos and, if you are lucky, spot a Mediterranean seal hunting for fish
  • Hike to the main town of Serifos and experience the “Iron island’s” coffee culture

Dates & Prices

Contact for information and pricing on our 2020 departures.

Included in the standard tour price

Accommodation: Sailboat charter for a week, Accommodation for up to 6 guests in double cabins

Meals : 7 breakfasts & 3 light lunches on board

Transport: Sailing boat rental costs, all electricity and water port costs, fuel costs, port authorities and marina fees

Tour Staff: Bearing True South tour leader, Bearing True South skipper, local guides when needed

All taxes including VAT

Not included in the standard tour price

Airline tickets to/from Athens
Transfers to/from the marina arranged if needed at an extra fee
Meals not listed in the inclusions
Personal expenses
Travel insurance
Optional activities as listed in ‘tour activities’
Local transport (such as taxis or buses on the islands)
Tips and Gratuities

Private Groups

If our dates don’t suit your plans, or if you want to experience one of our adventures with your family or group of friends, we can arrange a private tour just for you on the dates that suit you, based on one of our existing itineraries.
Furthermore, with a minimum number of 4 participants, all of our tours can be customized as far as date of departure, activities and itinerary are concerned, according to your group’s requirements. For groups of less than 4 travelers, standard tour prices are subject to change. In that case, please contact us in order to get a new quote.
For more information don’t hesitate to contact us with your ideas at : and we’ll get back to you shortly with detailed information and pricing.


If you want to arrange a private group tour based on this itinerary, please contact us with your ideas and we’ll get back to you shortly with detailed information and pricing.

Additional information


7 days

Level of Difficulty


Group Size

minimum 2 persons – maximum 8 persons per yacht


4 years and older, younger kids travel at their parents' discretion and responsibility