Are you dreaming of gazing at iconic whitewashed villages, exploring vibrant port towns, and sailing across crystal-clear waters? This 8-day cabin charter in Greece offers a chance to do just that — all aboard a luxury Jeanneau 54 DS sailing yacht. With stops in the Cyclades, Santorini, and Ios, guided by experienced skippers and chefs, this adventure is perfect for those wanting to combine authentic island life with a touch of luxury.
What we really love about this experience is the small group size — only four guests per boat — which promises an intimate, personalized trip. Plus, the delicious organic food prepared by your onboard chef ensures you’ll stay well-fed while soaking in breathtaking views. On the flip side, a possible consideration is the non-refundable booking policy, so it’s best to be sure of your plans before committing.
This tour suits travelers who crave a luxurious yet authentic sailing experience, enjoy good food, and don’t mind a little adventure on the water. Whether you’re celebrating a special occasion or just seeking a break from the ordinary, this trip offers a blend of relaxation, exploration, and a taste of real Greek hospitality.
Key Points
- Intimate Experience: Only four guests per boat ensure personalized attention and a quiet atmosphere.
- All-Inclusive Comfort: Air conditioning, generator, snorkeling gear, SUPs, and a chef for delicious meals.
- Flexible Itinerary: Visit iconic islands like Serifos, Syros, Kithnos, Hydra, and Spetses, with personalized stops and optional sailing lessons.
- Authentic Greek Flavors: Organic, fresh Mediterranean cuisine prepared onboard, with opportunities for cooking lessons.
- Beautiful Scenery: Expect stunning sea views, charming villages, and tranquil bays for swimming and relaxing.
- Practical Details: About $1,512 per person, with all the essentials included, but additional costs for fuel, port taxes, and drinks apply.
A Closer Look at Your Sailing Adventure in Greece
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Setting the Scene: Where and When
This sailing trip runs primarily in September, starting from Sifnos or Ios, and offers two main routes: the Cyclades and the Saronic Islands. The Cyclades itinerary begins from Lavrio and includes stops at Serifos, Syros, Kithnos, Zea, and more — perfect for those craving classic Greek island charm. The Saronic route takes you to Aegina, Poros, Hydra, and Spetses, providing a more urban and artistically vibrant experience.
The tour starts on Saturday afternoon, giving you time to settle in, meet your guides, and enjoy your first sunset from the deck. Disembarkation is the following Saturday morning, often in Piraeus or Santorini, making it easy to continue your Greek adventures afterward.
The Yacht: Comfort and Style Onboard
The Jeanneau 54 DS is a vessel renowned for its elegance and performance. The 17-meter yacht features generator, air conditioning, and luxury amenities, creating a home away from home on the water. Each of the two large double cabins comes with its own private bathroom and electric toilet, offering privacy and comfort on the open sea.
The hostess/chef prepares delicious, organic Mediterranean cuisine, adding a gourmet touch to your journey. Expect freshly baked croissants, local produce, and tapas-style dishes that complement the stunning scenery. The skipper has 30 years of sailing experience and is also an offshore sailing instructor — if you’re interested, you can even learn to sail or improve your skills.
What You Can Expect Each Day
Mornings start with a hearty breakfast — think croissants, fresh fruits, and local specialties — served on deck as the sun rises over the water. After breakfast, you’ll usually set sail for the next destination, with snorkeling gear, SUPs, and a dinghy available to explore nearby bays or relax onshore.
Lunch is a highlight — a delicious Mediterranean meal, often enjoyed in a beautiful bay after a swim. In the afternoons, the boat might sail to a new island or marina, giving you free evenings to stroll charming villages, enjoy local tavernas, or simply unwind on deck.
Some evenings feature candlelit dinners, creating a romantic, laid-back atmosphere. The small group size and flexible itinerary mean that your guides can pause longer in a bay you love or skip a destination if you prefer more sailing.
Authentic Experiences and Learning Opportunities
The trip offers more than just sightseeing — it’s about engaging with authentic Greek island life. The onboard cooking lessons with Luciana introduce you to Mediterranean flavors, while sailing lessons with Renato—who has 30 years of offshore experience—are available for those eager to learn the ropes.
From authentic local cuisine to personalized island visits, this voyage balances luxury and authenticity. The reviews highlight how memorable and well-organized the trip is — one traveler called it “exceeding every expectation” — and many appreciated the spotless boat and the delicious, fresh food.
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The Value Proposition
At about $1,512 per person, this experience offers private, luxury accommodations with many inclusions: snorkeling gear, SUPs, cooking and sailing lessons, and stunning scenery. The small group size amplifies the feeling of exclusivity and personal attention, making every day a tailored adventure. Additional costs, such as fuel, port taxes, and drinks, are extra, but overall, the trip promises excellent value compared to other luxury sailing options.
Who Will Love This Tour?
This sailing adventure is ideal for those who appreciate comfort but want an authentic Greek experience. If you love delicious food, charming islands, and learning new skills like sailing or cooking, you’ll find this trip especially rewarding. It’s also well-suited for couples, small groups, or families looking for a memorable, intimate holiday.
Keep in mind the non-refundable policy — it’s best to be confident about your travel dates. The small group size means it’s less suited for travelers seeking a large, social party atmosphere, but perfect for those wanting a peaceful, immersive experience.
Practical Info and FAQs
- What is included? The price covers accommodation, snorkeling gear, SUPs, dinghy, and meals prepared onboard.
- What’s not included? Fuel, port taxes (~$350 per week), and drinks.
- How many people? Only 4 guests per boat, ensuring a personalized experience.
- Are there sailing lessons? Yes, ** Renato** can give lessons if you’re interested.
- Is this suitable for beginners? Yes, with sailing instruction available, even novices can enjoy the experience.
- What is the best time to go? September, when the weather is still warm and the sea calm.
- How do I get there? The trip starts at Adamopoulou, Ios, with possible disembarkation at Piraeus or Santorini.
- What about accessibility? Most travelers can participate, but it’s not recommended for those with claustrophobia or asocial tendencies.
- Can I cancel if needed? No, the booking is non-refundable, so plan accordingly.
Final Thoughts
This sailing trip delivers a luxurious yet authentic dive into the heart of Greece’s islands. Beautiful scenery, delicious food, personalized service, and hands-on learning make it stand out from more commercial tours. It’s perfect for travelers who want to combine relaxation, adventure, and culture in a small, friendly setting.
Whether you’re celebrating, seeking a unique family vacation, or simply craving a peaceful escape on the water, this experience offers genuine value. Just be sure to confirm your plans before booking, given its non-refundable policy.
If you love stunning views, excellent cuisine, and a chance to learn some sailing or cooking skills while exploring Greece’s most beautiful islands, this tour might be your next favorite adventure.
9 Practical Questions & Answers
What islands will I visit?
You’ll visit islands like Serifos, Syros, Kithnos, Zea, Hydra, and Spetses, depending on the route chosen, each offering unique charm and scenery.
How long is the trip?
The trip lasts about 8 days, from Saturday afternoon to the following Saturday morning, with flexible itinerary options.
Can I get sailing lessons?
Yes, Renato, the skipper, is an offshore sailing instructor and can offer lessons if you want to learn or improve your sailing skills.
What kind of boat is used?
A luxury Jeanneau 54 DS, equipped with generator, air conditioning, private bathrooms, and modern amenities designed for comfort.
Is food provided?
Yes, a hostess/chef prepares fresh, organic Mediterranean meals onboard, including breakfast and lunch.
What should I bring?
Bring casual, comfortable clothes, swimwear, sun protection, and a sense of adventure. The boat provides beach towels, masks, fins, and SUPs.
Are meals and drinks included?
Meals are included, but alcohol and additional restaurant meals are extra and not included in the base price.
Is transportation to the start point arranged?
You are responsible for reaching Adamopoulou, Ios, but the trip ends at a convenient location like Piraeus or Santorini.
Can I cancel if I change my mind?
No, this experience is non-refundable, so double-check your plans before booking.
This sailing trip blends the magic of Greece’s islands with the comforts of a luxury yacht, making it a truly memorable way to experience the Mediterranean. Whether you’re celebrating something special or just wanting a peaceful escape, it offers a perfect mix of relaxation, adventure, and authentic local flavor.