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Adventure sailing & mile building holidays

Our adventure sailing trips are designed to provide longer sailing distances and a more adventurous itinerary than our cabin charters; excellent for someone hoping to build mileage or keen to complete longer sailing passages.

The emphasis is on sailing and may include passeage of 50 miles or more out to the Cyclades.

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Adventure sailing holidays in Greece

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An adventure sailing holiday or mile building trip, operates in a similar manner to a cabin charter holiday. You can book a single cabin (two berths), or if you and a group of friends wish to sail together, you can even book the entire yacht, and the more of you who book together, the lower the price each of you pay for your adventure sailing trip.

The key difference between our adventure sailing trips and cabin charters is the distances you are likely to cover and the style of sailing. Whereas our cabin charters are designed to provide a relaxed sailing holiday, our adventure sailing trips aim to allow you to build miles and experience with longer passages and more challenging sailing. You should expect more time at sea and to not always be in sight of land during an adventure sailing trip.

How Adventure Sailing trips work

A traditional fruit caique in Aegina harbour, one of the many sights you may see during your cabin charter sailing holiday with Greek Sails

Adventure sailing trips are run under the control of a skipper. This leaves the skipper to worry about safety & yacht management and allows you to enjoy the sailing. You also gain from the skipper’s sailing experience, familiarity with the yacht and extensive local knowledge.

The itinerary - where you sail to - is flexible and the crew are encouraged to discuss their ideas with the skipper. The skipper must, however, have the final say based on time, weather and the crew’s experience. Remember, your route may alter during the course of the week based on the weather or other conditions, although the skipper will always be happy to explain any changes with you.

With both an adventure sailing trip and cabin charter, you are required to help sail the yacht and help in preparing food, although food preparation is usually limited to snacks at lunchtime. A kitty system is usually the best option to cover the cost of food and drink eaten aboard. All crew members are also required to assist in keeping the yacht clean and tidy.

Evening meals are usually eaten ashore in a local taverna, quite probably over a beer or two after a good day’s sail, although you may cook aboard if you wish. Where you eat is your choice, although it’s worth listening to the skipper’s advice which is always based upon quality, location and value and not on kick backs!

Example adventure sailing itinerary

Each adventure sailing trip is a week-long itinerary designed to give you mileage and sailing experience. Where you sail will vary on many factors, including your input, but may include the Argolic Gulf, eastern Peloponnese or Cyclades islands. It’s worth you reading our notes on our sailing area and also checking our sailing holiday location albums to get some ideas on places you might like to visit...you never know, you might well get to visit many of the places you suggest.


Example Adventure Sailing trip
Sat Arrive in Poros (see ‘Travelling to Greek Sails’)
Sun Depart Poros to Ermioni, a lovely harbour to the south west of Poros
Mon Depart Ermioni to Tiros, a delightful small quiet harbour of fishing boats and tavernas
Tue Depart Tiros to Navplion, with its unmissable old town of neo-classical buildings and the huge Venetian Citadel of the Palamidi above
Wed Depart Navplion for Plaka (Leonídhion Plaka), considered one of the lovliest places in Greek waters
Thu Depart Plaka for Hydra, also considered one of the most beautiful ports in Greece with old merchants’ houses nestling around the harbour
Fri Depart Hydra for your return to Poros and a final evening meal in one of the many tavernas lining the Poros quayside
Sat Depart Poros to return to the real world

Pricing for adventure sailing trips

Pricing for our adventure sailing trips can be found in Table 5 on the ‘Sailing holiday, charter & learn to sail prices’ page.


Enjoy a cabin charter sailing holiday; relax and make new friends

Send an enquiry about a cabin charter sailing holiday with Greek Sails


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