Experience the magic of the Greek islands from a unique perspective on this 9-day sailing adventure. Navigate azure waters aboard a comfortable yacht, discover secluded beaches accessible only by boat, explore charming villages, and enjoy the relaxed pace of island life.
Welcome to Greece! Meet your captain and fellow sailors at Marina Kalamaki near Athens in the afternoon. After a safety briefing and orientation to your yacht, enjoy a welcome dinner at a local taverna. Overnight at the marina to prepare for your morning departure.
Set sail in the morning for Kea, a charming island off the beaten path. Enjoy lunch and a swimming stop in a secluded bay before docking at the picturesque port of Korissia. Evening walking tour of the traditional Ioulida village with its narrow streets and windmills, followed by dinner at a family-run taverna serving authentic Cycladic cuisine.
Morning sail to Kythnos with a stop at the famous Kolona Beach, a unique sandbar connecting the island to an islet. Afternoon exploration of the thermal springs of Loutra. Evening at the traditional port of Merihas, where you can wander the waterfront and enjoy fresh seafood at a local restaurant as the sun sets.
Sail to Serifos, known for its rugged mining landscape and stunning Chora (main town) perched dramatically on the hillside. Anchor in a secluded bay for lunch and swimming. Evening visit to Chora for spectacular sunset views and dinner at a traditional taverna overlooking the Aegean.
Morning sail to Sifnos, famous for its pottery and cuisine. Arrive at the beautiful bay of Vathy for lunch and relaxation on its golden sand beach. Afternoon cooking class learning traditional Greek dishes from a local chef. Evening at leisure to explore the charming harbor town of Kamares.
Early departure for Milos, famous for its unique volcanic landscapes and the discovery site of the Venus de Milo statue. Explore the island's extraordinary coastline with its colorful rock formations, stopping at Kleftiko caves (accessible only by boat) for swimming and snorkeling. Evening at the picturesque fishing village of Pollonia with its excellent seafood restaurants.
Sail to the less-visited island of Folegandros, one of the most authentic and unspoiled Cycladic islands. Enjoy swimming and snorkeling in crystal-clear waters of the Blue Caves. Evening visit to the stunning clifftop Chora with its medieval character. Dinner at a local taverna featuring farm-to-table ingredients from the island.
Morning sail to the iconic island of Santorini. Approach the dramatic caldera with its towering cliffs for a truly spectacular arrival. Afternoon wine tasting tour visiting three traditional wineries producing the island's distinctive volcanic wines. Evening farewell dinner in Oia with breathtaking sunset views over the caldera.
After breakfast, disembark from your yacht in Santorini. Optional extension stays available or transfer to Santorini Airport for departure flights. End of sailing services.
8 nights aboard a comfortable modern sailing yacht with 3-4 double cabins, shared bathrooms, indoor and outdoor common areas
8 breakfasts, 7 lunches, 3 dinners including welcome and farewell dinners, and daily snacks and refreshments aboard
Services of a professional, English-speaking skipper with extensive knowledge of the Greek islands
Snorkeling equipment, stand-up paddleboard, and swimming stops at secluded beaches and bays
Guided walking tours, cooking class on Sifnos, wine tasting on Santorini, and village visits throughout the journey
Marina fees, fuel, water, port taxes, cleaning fees, and a sailing trip photo album as a souvenir
Maximum of 8 travelers (typically 6-8) to ensure comfort aboard the yacht and an intimate experience at each destination
We sail on modern yachts typically 45-52 feet in length with:
• 3-4 double cabins with shared bathrooms (2:1 bathroom ratio)
• Indoor salon with dining area and basic kitchen facilities
• Spacious deck for sunbathing and outdoor dining
• Safety equipment exceeding international standards
• Electric fans in all cabins (no air conditioning as standard)
Note: While comfortable, yacht accommodations are cozy and require a spirit of adventure and cooperation.
Easy to Moderate - This sailing adventure requires basic mobility and comfort with water activities. You should be able to:
• Climb on and off the yacht using a short ladder
• Swim or at least be comfortable in water with a life jacket
• Walk on uneven terrain during island visits
No sailing experience is necessary, and participation in sailing activities is encouraged but optional.
This sailing adventure operates from May through October:
• May & October: Milder temperatures (70-80°F/21-27°C), fewer tourists, occasional cool winds
• June & September: Warm temperatures (75-85°F/24-30°C), moderate crowds, reliable winds
• July & August: Hot temperatures (80-90°F/27-33°C), busier islands, consistent meltemi winds
The nature of sailing means our itinerary may change based on weather conditions, wind patterns, and harbor availability. Your captain will make decisions prioritizing safety and comfort while ensuring you experience the best of the Greek islands. This flexibility is part of the adventure!
Our sailing adventures prioritize environmental responsibility and community support:
• Reduced plastic usage with filtered water systems aboard
• Environmentally friendly cleaning products and waste management
• Support for small, family-run businesses on islands
• Partnership with the Aegean Marine Life Sanctuary
• Carbon offset contribution included for each participant
This sailing adventure was absolutely magical! Captain Nikos was not only an expert sailor but also a wonderful host who knew all the secret spots away from the tourist crowds. Waking up in a different secluded bay each morning, jumping straight into crystal clear water, and then having breakfast on deck was paradise. The cabins were cozy but comfortable, and our group of 8 quickly became like family. Highlights included the sunset in Folegandros and swimming into the Kleftiko caves in Milos. If you're considering this trip - DO IT! Just pack light and bring a sense of adventure.
We celebrated our 25th anniversary on this sailing trip, and it exceeded all expectations. The islands each had their own distinct character - from cosmopolitan Santorini to untouched Folegandros. Our captain found the perfect balance of structured activities and free time. We particularly loved the cooking class on Sifnos where we made authentic moussaka. The yacht was more comfortable than we expected, though quarters are understandably tight. The real luxury was accessing gorgeous beaches and coves that larger ships can't reach. We've already recommended this trip to several friends.
What an incredible way to experience the Greek islands! As a solo traveler, I was a bit apprehensive about sharing such close quarters, but our group bonded quickly and the experience was fantastic. I appreciated that we visited both famous islands like Santorini and lesser-known gems like Kythnos, which felt authentically Greek. The food throughout was outstanding - especially the seafood restaurants our captain recommended. The only thing to be aware of is that sailing can be somewhat unpredictable - we had to modify our route slightly due to strong winds, but this is part of the sailing experience. Would definitely book another sailing adventure!
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