Imagine sailing through the iconic Cyclades, hopping from one picture-perfect Greek island to another, all aboard a cozy yet luxurious yacht. For $9,540 per group (up to 6 people), this five-day voyage takes you from Santorini’s caldera to secluded Koufonissi, lively Paros, tranquil Antiparos, and the famous beaches of Ios. Led by an experienced crew, including a skipper and deckhand, you’ll enjoy comfortable cabins, delicious meals, and the kind of views that make all the effort worthwhile.
What really makes this experience shine is the seamless blend of adventure and relaxation. We loved how the yacht’s well-appointed interior offered a cozy retreat after days of exploring, and the chance to wake up each morning to a new island vista is difficult to match. Plus, the flexible itinerary means you’re not locked into a rigid schedule—ideal for those who want authentic island time rather than just ticking boxes.
One thing to consider is that the cruise is weather-dependent. If storms roll in, the route could change or plans might be slightly altered. This is common in sailing trips, but it’s good to know before you set sail.
This tour suits travelers who crave intimate, authentic experiences, and those eager to explore the Cyclades beyond the usual crowded spots. It’s perfect for couples, friends, or small families who want a mix of adventure, comfort, and the chance to truly disconnect and enjoy Greece’s stunning seascape.
Key Points
- Comfortable Luxury: Well-designed vessel with three private cabins, linen, and bedding for a cozy stay.
- Authentic Island Hopping: Visit iconic islands like Santorini, Koufonissi, Paros, Antiparos, and Ios.
- Expert Crew: Skipper and deckhand ensure smooth sailing and attentive service.
- All-Inclusive Flexibility: Breakfast, one additional meal, fuel, taxes, and mooring fees are included.
- Weather Flexibility: Route adjustments possible due to weather conditions for safety and comfort.
- Personalized Experience: Private group booking offers a tailored, intimate adventure.
A Deep Dive into the 5-Day Sailing Adventure
Planning more time in Vlichada? We've covered other experiences worth considering.
Setting Sail from Santorini’s Vlychada Marina
Your adventure begins in Vlychada Marina, a unique harbor known for its lunar-like landscape and quiet charm. After a private transfer from your hotel or meeting point in Thera, you step aboard the Beneteau Oceanis 46.1, a vessel praised for its sleek design and comfort. The crew, experienced and passionate, will introduce themselves and brief you on the upcoming itinerary.
As your boat sets sail, you’ll enjoy views of Santorini’s famous caldera—a spectacle of white-washed buildings clinging to cliffs and volcanic islands. If you’re lucky, you’ll catch the sunset on your first evening, a reminder of why this region is considered one of the most breathtaking in Greece.
Day 1: Santorini to Koufonissi
Sailing through the caldera is an experience in itself. We loved the way the wind filled the sails, the gentle rocking of the boat, and the spectacular views of the volcanic landscape. Your first destination is Koufonissi, a tiny island with a reputation for natural beauty and tranquility. Here, you’ll spend your first night, giving you plenty of time to explore its secluded beaches and crystal-clear waters.
Guests have noted “plenty of time to marvel at its incredible beauty,” and the calm atmosphere is perfect for unwinding after a day of travel. The night in Koufonissi feels like a secret escape—quiet, beautiful, and a perfect way to start your island-hopping adventure.
Day 2: From Koufonissi to Paros
The next morning, your boat resumes its glide across the Aegean. The journey to Paros offers stunning views and the chance to relax on deck. Paros is a popular favorite, known for lively villages, beaches, and authentic Greek charm.
We appreciated the convenience of having a crew that handled navigation—allowing us to sit back and enjoy the scenery. Once docked, you can explore Paros’ charming villages, with their white-washed buildings and narrow streets, or simply relax on the beach. The evening offers a lively atmosphere, but plenty of quiet bays if you prefer solitude.
More Great Tours NearbyDay 3: To Antiparos
Sailing from Paros, you’ll reach Antiparos, a small island with a peaceful vibe. The white-and-blue scenery is postcard-perfect, and the laid-back atmosphere makes it a favorite for those seeking calm and authenticity.
Guests mention “a serene and idyllic atmosphere,” which is perfect for unwinding. You’ll spend your third night here, enjoying the quiet surroundings and perhaps a relaxed dinner ashore. The ship’s crew is happy to assist in finding local tavernas or hidden beaches for a true local experience.
Day 4: To Ios and Manganari Beach
On the fourth day, the boat heads to Ios, a lively and well-known island famous for its beaches and vibrant nightlife. However, the highlight here is Manganari Beach, often called the most beautiful beach of Ios. Its crystal-clear waters and soft sand evoke scenes from the movie “The Big Blue,” making it a hit for swimming and lounging.
Guests describe the landscape as “spectacular” and love having ample time to swim and relax. Spending your second night on Ios provides flexibility—whether you want to enjoy a quiet evening or experience some of the island’s famous energy.
Day 5: Return to Santorini
After breakfast, the cruise makes its way back to Vlychada Marina in Santorini. The journey offers one last chance to soak in the views, reflect on the trip, and enjoy the gentle sail. Disembarkation is smooth, with a driver ready to take you to your next destination.
What Makes this Yacht Trip Special?
The Comfort of a Well-Equipped Vessel
The Beneteau Oceanis 46.1 is praised for its modern, sleek design and spacious cabins. With three passenger cabins and two heads, it’s suitable for intimate groups who value privacy and comfort. Linen, bedding, and daily meals—breakfast and one other meal—are included, simplifying your day-to-day life on board.
Authentic Island Experiences
Travelers love the chance to visit less touristy, authentic spots like Koufonissi and Antiparos, which often get overshadowed by the more famous Santorini or Mykonos. The route offers a genuine taste of the Cyclades’ natural beauty and local life.
Flexibility and Personal Attention
The fact that the tour operates as a private group means your experience can be tailored to your preferences. The crew is passionate about making your trip memorable, and the itinerary can adapt depending on weather or your interests.
Cost & Value
At $9,540 for a five-day experience, the price includes most essentials—meals, fuel, taxes, mooring fees, and the expertise of a crew dedicated to your comfort. It’s an all-in-one package that offers a luxury experience without the hassle of planning each detail. You’ll also appreciate the transparent APA process, which covers additional expenses and ensures no surprise costs.
Considerations for Future Sailors
While the experience is largely positive, it’s worth noting that sailing trips are weather-dependent. If a storm or bad weather occurs, the route might shift for safety reasons. This is a standard caveat for such adventures but something to keep in mind when planning your trip. Plus, all on-board activities outside the included meals are your responsibility, so if you want to explore local tavernas or rent equipment ashore, those costs are extra.
Who Is This Tour Best For?
This cruise appeals most to those who enjoy a blend of adventure and relaxation, and who value authentic, small-scale experiences. It’s ideal for travelers who appreciate the idea of waking up in different beautiful locations, enjoying privacy, and having a knowledgeable crew handle the logistics. Couples, small groups of friends, or small families looking for a unique Greek island experience will find this to be a memorable way to explore the Cyclades.
If you’re someone who prefers big resorts and a packed itinerary, this might feel too intimate. But if you love the idea of a flexible, personalized journey through Greece’s most scenic islands, this trip could be perfect.
FAQ
What is included in the price?
The $9,540 fee covers transportation from your designated pick-up point, a skipper and deckhand, daily breakfast, one other meal, linen and bedding, and all expenses like fuel, taxes, and mooring fees (covered in the APA deposit).
Are all costs for off-board activities paid for separately?
Yes, all off-board activities or excursions outside the cruise are paid by the customer.
How many people can fit on the yacht?
The vessel accommodates up to 6 passengers comfortably in three private cabins, making it intimate but spacious enough for small groups.
What should I bring?
Bring casual, comfortable clothing suitable for warm weather, swimwear, sunscreen, a hat, and perhaps a light jacket for breezier evenings. The crew provides linens and bedding, so no need to pack those.
Can I customize the itinerary?
While the route follows a set schedule, the crew can adapt it depending on weather conditions or your preferences, making for a more personalized experience.
Is this experience suitable for children?
The tour is designed for private groups, and while not explicitly stated, small families or groups with children comfortable with sailing and island exploring should be fine. Check with the provider for age-specific considerations.
What happens if the weather disrupts the route?
The company reserves the right to modify or cancel the route due to weather. Safety is a priority, and the crew will communicate any changes.
How do I pay and book?
You can reserve now with a “Reserve & Pay Later” option, which is flexible and keeps your plans open. The APA deposit is already included in the total price, and full payment is due before departure.
To sum it up, this 5-day sailing trip offers a beautifully balanced mix of comfort, adventure, and authentic island charm. It’s a fantastic choice for anyone wanting to see the Cyclades from a different perspective—on the water, with stunning views and the personal touch of a dedicated crew. Whether you’re celebrating a special occasion or simply seeking a unique way to discover Greece’s islands, this cruise combines the best of everything for a memorable voyage.
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