The Ionian Sea is celebrated as one of the world’s premier sailing destinations, renowned for the breathtaking beauty of its islands, crystal-clear blue waters, and gentle summer winds. The northwest winds, known locally as “maistro,” offer far more favorable sailing conditions than the more intense “meltemi” winds found in the Aegean Sea. The Ionian islands offer a variety of activities, from historical sightseeing and ancient site exploration to delightful dining experiences in local taverns and restaurants. For those seeking vibrant nightlife, the islands present diverse options to suit all tastes.
Discover more about the enchanting Ionian Sea and consider joining our American Sailing online class hosted by Captain Dimitris Bampakos, the founder and owner of Fair Winds Sailing Greece. In this session, you’ll gain insights into sailing and bareboat chartering in Greek waters, providing a comprehensive overview of everything you need to know for an unforgettable sailing experience.
• The charter of the yacht.
• A full-time captain / American Sailing instructor.
• Harbor fees, marina fees, all government and local taxes.
• Professional cleaning of the yacht prior to and after the cruise.
• Linens (sheets, towels, blankets).
• Grocery provisioning for breakfast and lunch onboard plus snacks, bottled water, soft drinks, juices and ice.
• All fuel and freshwater costs.
• Your American Sailing certifications (instruction, American Sailing admin – not the books which can be ordered online).
• Alcoholic beverages.
• Evening meals on shore.
• Tips.
Join us for an unforgettable Learn to Sail vacation in Greece! Set sail on the beautiful Ionian Sea on one of our scheduled trips from May 16 to May 23, 2026 and May 23 – May 30, 2026. If you’re interested in exploring the breathtaking Greek islands but need alternative dates, please don’t hesitate to reach out—we’re happy to accommodate!
Captain Dimitris Bampakos, ASA Senior Master Instructor & founder and lead instructor of Fair Winds Sailing Greece, is a distinguished former Captain of the Greek Navy and an American Sailing Senior Master Instructor (SMI).
Throughout his 26-year Navy career, Captain Bampakos dedicated the majority of his time at sea, serving as captain, executive officer, and deck officer on frigates and fast patrol boats. His extensive experience includes over 100,000 nautical miles across the globe.
After commanding his final warship in 2006, he began cruising and racing each summer in the Mediterranean. Between 2013 and 2016, while stationed in Virginia, USA, Captain Bampakos completed all American Sailing certifications up to the offshore ocean passage level (ASA 108) and became an ASA instructor up to ASA 206. During this time, he also sailed in the Chesapeake Bay, the North Atlantic, and the North Pacific Ocean, proudly joining Patriot Sailing and BBSA.
In 2020, Captain Bampakos was invited to Los Angeles by American Sailing to participate in an Instructor Evaluator Qualification Clinic. Upon successful completion, he earned the title of Master Instructor. In 2023, he led another Instructor Evaluator Qualification Clinic in Tampa Bay, Florida, advancing to Senior Master Instructor.
Captain Bampakos is a graduate of the National Defense University, USA, holding an MSc. in Electronic Systems Engineering. Since 2000, he has also taught radar and naval communication systems at a postgraduate level.
For more about Captain Bampakos’s career and credentials, visit his Featured Instructor page on the American Sailing website. You can also read reviews from his students on Google.
Depending on your sailing experience and your certifications, this learn-to-sail vacation with Fair Winds Sailing Greece can offer a selection of the following certifications:
¤ ASA 103 | COASTAL CRUISING
¤ ASA 104 | BAREBOAT CRUISING
¤ ASA 114 | CRUISING CATAMARAN
¤ ASA 118 | DOCKING ENDORSEMENT
We’ll embark on an unforgettable journey through the Central Ionian Sea; the beautiful stretch of water nestled between the Greek and Italian mainland. Our starting point is Lefkas Marina. This prestigious marina is located just a few minutes from Lefkas island’s historic center, and it is the ideal base for exploring the stunning coastline of Central Ionian Sea.
We will start from there and sail to the islands of Ithaka, Kefalonia, Meganisi, Kastos, and Kalamos. Known as one of the premier sailing destinations in the Mediterranean, this area promises breathtaking landscapes, crystal-clear waters, and a rich tapestry of history and culture.
Please Note. This itinerary is meant to serve as an example, however, it is important to note that the actual itinerary is subject to change due to weather conditions or circumstances beyond our control.
*The pictures are from the official Lagoon website. If the aforementioned yacht is not available for any reason she will be replaced by a similar one.
Highly recommend. World class sailing instruction in one of the best sailing areas in the world. Dimitris is as skilled and experienced as a captain and instructor as he is friendly and kind. I did my ASA 105/6 with him and I consider it the inflection point when I became a confident and independent sailor. In addition to learning so much about sailing, I also made lifelong sailing buddies. A memorable and valuable experience all around!
I had the privilege of taking sailing lessons with Dimitris, and I can’t recommend him highly enough! My goal was to achieve my ASA 103 and 104 certifications, and Fair Winds Sailing made the entire process not only achievable but also incredibly enjoyable. Dimitris emphasized the importance of proper sailing rules and safety procedures. His thorough understanding of these principles gave me confidence on the water. What really stood out to me was Dimitris’s passion for sailing. If you’re looking to get ASA certified, I wholeheartedly recommend Fair Winds. You won’t just learn to navigate the waters—you’ll gain a deep respect for sailing and a lifelong love for the sport. Thank you, Dimitris, for such an outstanding experience!
