cabin charter in September, sailing boat, CYCLADES, SANTORINI, with CHEF

Exploring the Greek Islands by Cabin Charter on a Sailing Boat with a Chef

Imagine waking up to the gentle sway of a 17-meter Jeanneau 54 DS yacht while surrounded by the sparkling waters of Greece’s iconic Cyclades and Santorini. This private cabin charter promises a week of stunning scenery, delicious Mediterranean cuisine, and the freedom to set your own pace among some of the most beautiful islands in the world.

What makes this experience particularly appealing are its luxury touches—with only four guests, you’re promised an intimate atmosphere, personalized service, and the chance to learn sailing skills if you’re interested. Plus, the inclusion of a chef ensures every meal is a delight, making this a well-rounded, stress-free adventure.

One thing to keep in mind: the cost of around $1,512 per person covers most essentials but excludes galley, fuel, and port taxes, so it’s worth considering the overall value for such a tailored, boutique experience. This tour is best suited for travelers craving authenticity, comfort, and a touch of adventure all in one.

Good To Know

• Intimate Experience: Only four guests on board ensures personalized attention and a relaxed atmosphere.
• Luxury Comforts: Spacious double cabins with private bathrooms and air conditioning make for a comfortable journey.
• Authentic Sailing: Guests can learn sailing from an experienced skipper or simply enjoy the scenic rides.
• Gourmet Food: A dedicated chef prepares fresh, organic Mediterranean meals, often enjoyed in beautiful bays.
• Flexible Itinerary: Options include the Cyclades, Saronic Islands, or Peloponnese, with stops at major islands and hidden gems.
• All-Inclusive Feel: Snorkeling gear, SUPs, and dinghy are included, offering plenty of ways to enjoy the sea.

An In-Depth Look at the Experience

The Boat and Accommodation

The Jeanneau 54 DS yacht is a standout feature of this tour. Measuring at 17 meters, it combines elegance with practicality. Its generator and air conditioning guarantee comfort, even in the warmer months. With only four guests sharing two large double cabins, your space is both private and spacious, complete with en suite bathrooms and electric toilets.

Guests have praised the boat’s cleanliness and stylish design, which helps elevate the trip from just a cruise to a luxurious escape. The fact that beds are pre-made and sanitized adds peace of mind, especially important in today’s health-conscious environment.

The Itinerary and Destinations

The tour begins on Saturday from Sifnos on September 13, heading to the Cyclades. You’ll visit islands such as Serifos, Syros, Kithnos, and Zea. Each location has its own charm—Serifos with its rugged landscapes, Syros for its lively town vibe, and Kithnos for tranquil beaches.

On the following week, the focus shifts to the Saronic Islands—Aegina, Poros, Hydra, Spetses, and Ermioni. These islands are known for their picturesque harbors, vibrant tavernas, and historical sites. Guests can expect a mix of swimming, sightseeing, and relaxing evenings at marinas or anchoring in idyllic bays.

The flexibility of the itinerary is a big plus. You can choose the route that suits your interests, whether you’re after lively nightlife, quiet beaches, or cultural explorations.

What to Expect Daily

Mornings typically start with a hearty, freshly prepared breakfast—croissants, seasonal fruit, and locally sourced produce—set in stunning surroundings. After breakfast, the boat can sail to a new destination, giving you a chance to watch the landscape change with each move.

Afternoons often involve long swims, snorkeling, or paddleboarding with supplied equipment. The dinghy with an outboard allows you to explore shallower coves or visit small islands that are otherwise unreachable.

Lunches are a highlight, with the chef preparing Mediterranean cuisine in the boat’s galley, often enjoyed in a scenic bay after a long swim. Guests have raved about the food, highlighting its freshness and flavor. You might find yourself craving the organic, home-cooked meals even after the trip ends.

Evenings alternate between gourmet dinners ashore or onboard with candlelit settings. The smaller group size fosters intimate conversations and authentic connection. Some nights include optional sailing lessons, if you’re interested in learning the ropes from Renato, the knowledgeable skipper with 30 years of experience.

Activities and Extras

The tour naturally lends itself to sea-based activities: snorkeling in translucent waters, paddleboarding with SUPs, or simply relaxing on deck with a good book. For those eager to learn, sailing lessons are available, adding a valuable skill to your travel repertoire.

The inclusion of snorkeling equipment, SUPs, and a dinghy with outboard means you won’t be short of options to enjoy the sea. Plus, the crew’s local knowledge ensures you can discover the best hidden beaches and quiet anchorage spots.

Pricing and Value

At $1,512.09 per person, this tour offers a lot of value, especially considering the inclusion of accommodation, most activities, meals, and personalized service. The price does exclude galley, fuel, and port taxes, which add approximately $350 per person per week—a reasonable supplement given the luxury experience you’re getting.

Compare this to similar luxury boat experiences, and you’ll see that the private cabins, gourmet meals, and tailored itinerary make this a compelling choice for those who want a true personalized sailing holiday in Greece.

Authentic Feedback

Reviewers have expressed high satisfaction with their trips. One reviewer from Tripadvisor described their experience as “unforgettable”, praising the boat’s cleanliness and the atmosphere created by Renato and Luciana. They appreciated the sailing lessons and the chance to explore multiple islands comfortably, without feeling rushed.

Another reviewer highlighted how the boat’s elegance and comfort exceeded expectations, emphasizing the value of having private bathrooms and air conditioning—significant perks on a boat.

Who is This Tour Best For?

This sailing experience appeals most to travelers seeking a luxury, intimate escape with a personalized touch. It’s perfect for those interested in learning sailing, enjoying gourmet Mediterranean cuisine, and exploring multiple islands without the hassle of moving hotels.

It suits couples, small groups of friends, or even family groups who want a quiet, relaxing holiday with plenty of sea activities and cultural stops. While the experience is not recommended for claustrophobic or asocial travelers, it’s ideal for those who appreciate comfort, authenticity, and adventure in a small-group setting.

The Sum Up

This cabin charter in Greece offers a well-balanced combination of luxury, adventure, and authenticity. The small group size, private cabins, and gourmet meals create a spoiled-by-choice atmosphere, making it ideal for those who value comfort but also crave genuine sea-based exploration.

The flexibility of the itinerary, along with the knowledgeable crew and the inclusion of sailing lessons, means you’ll leave with new experiences and memories that last. Whether you’re lounging in a bay with a glass of local wine or learning to harness the wind’s power, this trip promises a personalized, scenic, and indulgent Greek island escape.

If you’re looking for a high-end sailing adventure that combines comfort, culture, and fun, this tour is worth considering. It’s best suited for travelers eager for a private, tailored holiday that balances relaxation with a touch of learning and exploration.

FAQ

What islands will we visit on this tour?
You’ll explore the Cyclades islands like Serifos, Syros, Kithnos, and Zea or the Saronic Islands including Aegina, Poros, Hydra, Spetses, and Ermioni, depending on your chosen itinerary.

How many people will be on the boat?
The yacht is designed for just 4 guests, ensuring a very intimate experience with plenty of personalized attention.

Is sailing included in the experience?
Yes, you can enjoy sailing and even take lessons from Renato, who brings 30 years of offshore sailing experience.

What meals are provided?
A dedicated chef prepares fresh, organic Mediterranean cuisine, including breakfast, lunch, and dinner, often enjoyed in scenic bays or onboard under the stars.

Are water activities included?
Yes, snorkeling gear, SUPs, and a dinghy with outboard are included, allowing you to explore the sea actively.

What’s the best time to go?
The tour runs from September 13 to 20 and 20 to 27, with ideal weather and calm seas, perfect for sightseeing and swimming.

What are the additional costs?
Galley, fuel, and port taxes are approximately $350 per person per week, which is not included in the base price.

Is this experience suitable for children?
While not explicitly stated, the tour’s small-group and active nature suggest it’s better suited for adult travelers or older children comfortable with sailing and water activities.

This sailing holiday blends the joys of discovery with the comfort of luxury, making it an excellent choice for those wanting a unique and personal Greek island adventure.