If sailing through the crystal-clear waters of the Ionian Sea is on your bucket list, this flotilla is the adventure you’ve been waiting for. Situated on the western coast of Greece, just south of the Adriatic, the Ionian Sea boasts stunning landscapes, rich history, and a vibrant local culture—making it the ideal setting for an unforgettable sailing experience. This flotilla offers the perfect combination of thrilling sailing, renowned Greek hospitality, fascinating ancient history, and exceptional local cuisine. Whether you’re an experienced sailor or a first-time adventurer, this journey is sure to captivate and inspire. And for those who’ve joined us on previous adventures in Croatia, Turkey, Italy, Spain, or the Seychelles, you know we create experiences that are both exhilarating and memorable.
Captain Don Doggett, owner of Sea Safaris Sailing School in Milwaukee, holds a USCG 100-Ton Master Captain’s License and is an ASA Senior Master Instructor. Sailing has been his passion since a very young age, and he has dedicated his career to sharing that passion by training and mentoring sailors of all experience levels.
A successful entrepreneur as well as an accomplished mariner, Captain Don is passionate about promoting sailing education and maritime skills. His dedication to teaching and mentoring has inspired countless sailors throughout the United States, and his friendly, approachable style makes him a valued member of our flotilla team.
Vere Stuij, Our flotilla leader from the Netherlands, completed her training in South Africa and holds an RYA/MCA Yachtmaster certification. She brings a wealth of experience as both a flotilla leader and professional skipper, having sailed extensively throughout the Mediterranean and the Caribbean.
Highly organized and dependable, Vere is the driving force behind keeping the flotilla program running smoothly. From coordinating daily activities to ensuring every detail is taken care of, she helps create a seamless experience for both guests and crew. Known for her warm personality, helpful nature, and infectious enthusiasm, Vere’s positive energy and leadership make every sailing adventure enjoyable, memorable, and stress-free.
Discover the beauty of Greece’s Ionian Sea, where crystal-clear waters, charming island villages, and unforgettable sailing come together. Departing from Lefkada, this flotilla offers the perfect blend of relaxed sailing, stunning anchorages, and great company. Explore picturesque islands such as Meganisi, Kalamos, and Kefalonia, visit the spectacular Papanikolis Cave, stroll through the colorful harbor of Fiskardo, and experience authentic Greek hospitality. Along the way, enjoy optional excursions including the Monastery of Agios Gerasimos, a tasting at the renowned Robola Winery, scenic hikes, and delicious local cuisine. Whether you’re seeking adventure, relaxation, or new sailing friendships, the Ionian Islands promise an unforgettable week on the water.
After a relaxing breakfast, we’ll set sail for the legendary Papanikolis Cave on the southern shore of Meganisi. This awe-inspiring cave, known for its massive entrance, is said to have once hidden a submarine during wartime. We’ll drop anchor here and take a refreshing swim in the crystal-clear waters that flow through the cave, making this a truly unforgettable stop on our journey.
Next, we’ll head towards the serene Afales Beach on the island of Ithaca, where the sparkling turquoise waters invite another dip in paradise. Afterward, we’ll set our course for the charming village of Fiskardo on the island of Kefalonia, where we’ll bask in its relaxed ambiance, picturesque harbor, and timeless beauty—perfect for soaking in the tranquil island vibe.
As we depart from Fiskardo, we’ll sail south through the scenic channel between Kefalonia and Ithaca, heading toward the port of Sami, about 12 nautical miles away. Along the way, we’ll glide past a series of breathtaking bays with untouched beaches, offering the perfect opportunity to drop anchor and dive into the crystal-clear waters for a swim.
Upon our arrival in Sami, where we’ll spend the night, an exciting land excursion awaits. One of the highlights is a visit to the famous Melissani Cave, located just outside the village. Steeped in myth, it’s said that the nymph Melissani leapt to her death in these very waters after being spurned by the Greek god Pan. Today, the cave stands as a stunning geological wonder, with its vibrant turquoise waters and a collapsed ceiling that allows sunlight to pour in, creating an ethereal glow. The atmosphere inside the cave is as magical as the legend that surrounds it.
As we continue our journey, we have an exciting day ahead with land tours lined up. We’ll visit the Monastery of Agios Gerasimos, a serene and sacred site, followed by a delightful wine tasting at the Cooperative of Producers of Robola of Kefalonia, where we’ll experience the rich flavors of the region’s famous Robola wine. Our destination for the night is the breathtaking Bay of Filiatro, where we’ll anchor and secure our boats to the rocks, rafting together to create a cozy and fun atmosphere. It promises to be a memorable day filled with adventure, culture, and stunning sights!
Our next destination is the picturesque island of Kalamos, where the charming port bears its name. Upon arrival, George will be there to welcome us, ready to assist with securing our boats before we head to his delightful restaurant for a delicious dinner.
Before reaching Kalamos, we’ll make a stop at the stunning One House Bay on Atokos Island. This hidden gem is the perfect place to anchor and dive into the crystal-clear waters, swim beneath towering cliffs, or relax on the pristine, secluded beach. Though privately owned, we’re graciously invited to explore this wild, cavernous paradise, offering a truly unique experience.
Tonight, we’ll come together for a festive Greek celebration with our lively white party, where the fun, music, and local spirit will make for an unforgettable evening!
It’s a lazy morning for some and a chance to explore town for others, depending on how much you partied last night! Today, we’ll set sail for Vlycho Bay, where the scenery will offer a delightful contrast to our adventures throughout the week. The vibrant colors of the water and the sight of numerous boats anchored in the bay create a picturesque, floating town ambiance that’s sure to captivate you.
Tonight, prepare to be amazed by a delicious meal at Hippocampus in the nearby town of Akhouria. It promises to be a perfect ending to a day of relaxation and stunning views!
That’s a wrap, folks! It’s our final day, and we’ll begin our journey back to our base in Lefkas. But don’t worry, the adventure isn’t over just yet! Along the way, we’ll have plenty of chances to stop at a few more stunning bays, each with pristine beaches ideal for one last swim or sail. Soak in the breathtaking Ionian views as we enjoy a delicious final lunch on board, savoring the memories of our incredible journey.
Afterward, we’ll set sail for the last leg back to Lefkas. You’re welcome to stay aboard for a cozy final night or, if you prefer, treat yourself to the comfort of a hotel stay, complete with a real shower and bed to unwind after a week of sailing.
Disembark by 9:00 am and go home with memories of a lifetime.
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.
My husband and I have joined 3 flotillas and have found that Captain Jean’s experience as a sailor and his knowledge of the cruising waters along with “Admiral” Mila’s knack for finding the finest restaurants and interesting places to visit on shore makes Med Sailing Adventures a fantastic, one-of-a-kind vacation! We look forward to many more trips with them.
It was fantastic to have somebody who knows the areas, the vendors and the best restaurants! I would never have found such hidden gems if it were not for their leadership. I had a great time, made new friends who love to sail and enjoy good food!
