By the time May 2026 came around, I had just about all the sailing education & training that one can ask for. I had just completed certification for the RYA Ocean Theory course, which covers celestial navigation and long passage planning & management. Since I’m already certified up to ASA 106, the next step in my training & certification journey would be to start progressing towards the RYA Yachtmaster Offshore certification, which is the industry-recognized standard for sailing competency, allowing you to work professionally on sailing vessels.
But although I have plenty of experience as crew, including an Atlantic crossing, my sailing resume as skipper consists of only short day sails. The next step in leveling up my sailing competency is now a focus on skippering “bareboat”. which means renting out a boat with no crew, where I am the skipper and the people I bring on board serve as crew.
So when my wife’s brother was considering a vacation oin Greece with his two daughters, she proposed a bareboat charter to him, where Jenn and I can start gaining experience managing the sailboat, and her brother and his girls can enjoy a nice week out in the Saronic Islands.
We ended up having a great time, and Jenn and I gained valuable experience and knowledge in anchoring and docking, specifically the “stern-to” docking method used primarily in the Mediterranean.
The below posts document the entire trip, from the planning phase all the way to the time we returned the boat to its berth at the end of the charter.
- 2026 Greece: Planning
- 2026 Greece: First Day of Charter
- 2026 Greece: Athens to Aegina (Day 2)
- 2026 Greece: Docking Drills (Day 2)
- 2026 Greece: Aegina to Ermioni to Dokos (Day 3)
- 2026 Greece: Chill Day in Dokos (Day 4)
- 2026 Greece: Dokos to Hydra (Day 5)
- Greece 2026: Hydra to Agistri via Poros (Day 6)
- Greece 2026: Agistri to Athens (Day 7)
And below are the two maps showing the itinerary we followed.


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