Gentle Sailing

Sailing in Greece

A Unique Experience

  • Sailing between different places
  • Stopping in cosy harbours
  • Anchoring in beautiful bays
  • Taking the helm and hoisting the sails yourself
  • Watching amazing sunsets
  • Sleeping under a star-spangled sky
  • Swimming and snorkelling on a daily basis
  • Using the dinghy to go exploring
  • Enjoying specialities and delicacies in local restaurants
  • Going for a walk on islands
  • Relaxing with a good book on deck
  • Enjoying the sea, surroundings, and freedom
  • Slowing down at 100km/h

Curious as to how this takes shape in reality? Find out here!

Poros – Greece

A trip with Gentle Sailing begins and ends in Poros, a quick ferry ride away from Athens. From Poros, a lot of wonderful courses are possible:

  • the Saronic Gulf with Poros, Aegina, Epidaurus, Korfos, Angistri, …
  • the Argolic Gulf with Hydra, Spetses, Dokos, Ermioni, Porto Cheli, …
  • the Peloponnese with Vivari, Nafplio, Astros, Kyparissi, …

We go where the wind takes us. We begin with a plan A. But if the wind shifts, we make a plan B. Or C. Maybe even a plan D, who knows? Wherever the wind may take us, the region around Poros makes sure to offer lovely bays or cosy harbours within sailing distance.g is hiervoor gemaakt: waar de wind ons ook brengt, er is altijd een mooie baai of fijne haven op zeilafstand.

The region is a well-known sailing area with favourable wind conditions. In case of winds higher than Beaufort force 6, we won’t set sail but will remain in the harbour and keep busy on the island. 

The boat

You will set foot on a keelboat with 3 or 4 cabins (bedrooms), depending on the number of passengers. Every cabin has a double bed. On top of that, the boat consists of a kitchen, sitting and dining area, and 1 or 2 shared toilets / showers. The boat provides accommodation, as well as transportation. You can think of it as a camper van on water.

Gentle Sailing collaborates with Greek Sails, a Flemish-Greek family owned business that has been renting out sailing boats in Poros. A friendly and welcoming business with an excellent service.

Tom

My sailing journey begins at 17 years old, when I started off with dinghy sailing, before moving on to larger sailing boats with cabins. I was taught to sail in Greece by my dear friend Captain Willy, who showed me the knowledge, the skill, the peace, the fun. In 2007, I obtained my Yachtman certificate at the Flemish Sailing School. In 2018, I also obtained my teaching certificate and started teaching sailing at sea for the Flemish Sailing School. I have been sailing for over 25 years in Greece, Croatia, and Türkiye with keelboats ranging from 32 tot 48 feet (10 to 15 metres). Given that the sailing and boat lifestyle is a group event, I make sure to keep an eye out to be able to guarantee good vibes on board.

Cost

(for the 2026 season)

6 people: €680 / person

5 people: €820 / person

Would you like to join on your own or does your group consist of 3 or 4 people? Don’t hesitate to contact me to discuss your options.

This price will get you: boat’s rent, skipper, bed sheets, towels, outboard motor, administration (Transit Log), final cleaning

Additional costs: trip to and from Poros, costs for provisions on board and in restaurants (the skipper’s meals included), harbour fees, boat water top-ups, used fuel costs

Available Trips 2026

Sunday 13/09/2026 – Saturday 19/09/2026

Sunday 20/09/2026 – Saturday 26/09/2026

Sunday 27/09/2026 – Saturday 3/10/2026

Sunday 4/10/2026 – Saturday 10/10/2026

Sunday 11/10/2026 – Saturday 17/10/2026

Sunday 18/10/2026 – Saturday 24/10/2026

Available trips 2027

(costs 2027 trips available 1/12/2026 on this website)

  • Sunday 3/10/2027 – Saturday 9/10/2027: FULLY BOOKED
  • Sunday 10/10/2027 – Saturday 16/10/2027: 6 spots left
  • Sunday 17/10/2027 – Saturday 23/10/2027: 6 spots left
  • Sunday 24/10/2027 – Saturday 30/10/2027: 6 spots left
  • Sunday 31/10/2027 – Saturday 6/11/2027: FULLY BOOKED

Booking – Information – Questions

Would you like to book a trip? Or would you like some additional information about what we offer? Would you rather like to learn how to sail or improve your sailing skills? I provide both an in depth, entry-level, 5-day Competent Crew course or a course for more experienced sailors to help you grow more confident in skills such as course planning, harbour moves, and anchoring.

Gentle Sailing

Tom Oosterlinck

Business Registration Number 0557.959.638

tom@gentlesailing.be