Greece · July 5 - 12 2025

Greece Flotilla - Southern Ionian

Set Sail from Lefkada: Adventure Awaits in the Heart of the Ionian Sea

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Overview

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.

Itinerary

Set sail through the crystal-clear waters of the Ionian Sea, a region steeped in history, beauty, and vibrant local culture. Located on the western coast of Greece, just south of the Adriatic Sea, the Ionian offers a breathtaking mix of dramatic landscapes, hidden beaches, and charming islands, all waiting to be discovered. Departing from Lefkada, this flotilla strikes the perfect balance between thrilling sailing and camaraderie with fellow adventurers. Along the way, you’ll explore picturesque islands like Meganisi and Kalamos, marvel at the stunning Papanikolis Cave, and unwind in the lively town of Fiskardo. Each stop along the journey offers something unique, whether it’s swimming in crystal-clear waters, hiking historic trails, or experiencing the warmth of Greek hospitality. You’ll also have the opportunity to visit the Monastery of Agios Gerasimos, enjoy a wine-tasting experience at the renowned Robola Winery, and savor some of the finest local cuisine. With every turn, you’ll uncover ancient myths and stories that have shaped this beautiful region. Join us for a once-in-a-lifetime sailing adventure, where each new destination promises discovery, excitement, and unforgettable memories.

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SATURDAY

After a leisurely morning, the flotilla leaders will gather the crew for an exciting provisioning adventure, exploring the vibrant local markets and charming grocery stores. Being in Greece, we’ll of course indulge in the finest Greek delicacies. Our focus will be on stocking up for delicious breakfasts and lunches, with plenty of local produce, cheeses, and fresh bread. And, naturally, we’ll secure an ample supply of excellent Greek wines and Ouzo to set the tone for the perfect Mediterranean experience.

Once the yachts are checked in and the chart orientations are complete, we’ll be ready to set sail. By 17:00, we’ll cast off and embark on our first leg to Meganisi Island, just 10 nautical miles away. We’ll dock in the picturesque harbor of Vathi, where you can relax and unwind at one of the local restaurants near the marina, enjoying a hearty Greek meal to cap off a wonderful first day at sea.

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SUNDAY

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.

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MONDAY

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.

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TUESDAY

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!

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WEDNESDAY

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!

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THURSDAY

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 Vilcho 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!

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FRIDAY

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.

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SATURDAY

Disembark by 9:00 am and go home with memories of a lifetime.

Hosts

Spiros Kavvadas

Spiros Kavvadas

Since 2022, Spiros Kavvadas has been our dedicated flotilla leader, bringing a wealth of experience and a deep-rooted passion for the Ionian Sea. A seasoned local sailor, Spiros’ intimate knowledge of these waters, coupled with his genuine love for sailing, ensures an unforgettable journey for all aboard. His expertise and dedication make him the ideal guide to lead our flotilla through the stunning landscapes and rich history of the Ionian islands.

Capt. Jean and

Capt. Jean and "Admiral" Mila

Jean and Mila are the dynamic duo behind Whitecaps Sailing, combining their unique expertise and passion for sailing to offer unforgettable experiences on the water.

Jean, originally from Belgium, holds a U.S. Coast Guard Captain’s license and is a Master 100T. He is also a certified sailing instructor with the American Sailing Association and is actively involved in yacht brokerage. With years of experience on both private and chartered vessels, Jean’s skills and leadership on the water are unparalleled.

Mila, born and raised in Peru, also holds a U.S. Coast Guard Captain’s license.  She is the heart and soul of their operations—acting as the Admiral of the flotilla, master organizer, and the strong, reliable first mate. Her behind-the-scenes and leadership are key to their success.

Together, Jean and Mila have been organizing ASA flotilla sailing trips since 2009. Their extensive knowledge of the Mediterranean and other idyllic sailing destinations guarantees that your sailing adventure will be nothing short of spectacular.

They also own Whitecaps Sailing, an ASA-certified sailing school based in Punta Gorda, Florida. Through their school, Jean and Mila offer ASA certifications in a fun and relaxed vacation atmosphere during the summer months in the Mediterranean.

In addition, Jean and Mila are proud to be the trusted charter brokers of Med Sailing Adventures, helping clients find attractive bareboat charter rates with top-tier charter companies worldwide.

Whether you’re looking to learn, explore, or relax, Jean and Mila are here to make your sailing experience extraordinary.

Yachts

Monohull

Monohull

FROM$2,295.00/pp

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Catamaran Cabin

Catamaran Cabin

FROM$2,395.00/pp

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Greece Flotilla - Southern Ionian

Greece · July 5 - 12 2025 · 7 nights

FROM$2,295.00/pp

BOOK NOW