Santorini: Ios Island Overnight Sailing Trip with Meals

Planning a trip to Greece and craving a unique way to explore the Cyclades? This overnight sailing tour from Santorini to Ios offers a blend of scenic beauty, luxury, and authentic island charm that’s hard to beat. While the price of around $3,952 per group might seem steep at first glance, it covers a two-day adventure filled with comfort, local flavors, and unforgettable vistas.

What we love about this experience is the opportunity to sail aboard a luxury sailboat, enjoy delicious curated meals, and take in breathtaking views without the hustle of crowded tours. The relaxing on deck with a glass of good wine, the chance to swim at Magganari Beach, and the freedom to explore Ios at your own pace make this an ideal escape for those seeking both adventure and tranquility.

One thing to consider is the cost, which is on the higher side, but for many travelers, the all-inclusive nature and personal service justify the expense. This tour suits adventurous couples, small groups, or those wanting a more intimate experience with Greece’s islands, especially if you value comfort and flexibility over busier, larger tours.

Good To Know

• Luxury Sailing Experience: A private group trip aboard the well-appointed Kymatia Sailboat.
• All-Inclusive Comfort: Includes cabins, fine wine, local delicacies, and a leisurely breakfast.
• Stunning Scenery: Panoramic views of volcanic cliffs, turquoise waters, and picturesque sunsets.
• Authentic Island Exploration: Free time on Ios to visit beaches, towns, or simply relax.
• Ideal for Relaxation and Fun: Perfect for those craving a laid-back, intimate experience.
• Weather & Seasick Considerations: Check weather and prepare for seasickness if prone—it’s a sailing adventure, after all.

You can check if your dates are available here:

Setting Sail from Santorini: What to Expect

The experience begins with a departure from Santorini’s stunning coastline aboard the Kymatia Sailboat, a vessel that combines comfort and style. The crew, acclaimed for their attentive service, sets the tone for a relaxing journey as you leave behind the crowds and venture into the open waters of the Aegean.

The first hours on board are about soaking in the scenic views. You’ll see volcanic cliffs, whitewashed villages, and blue-domed churches from the deck—picturesque sights that look even more spectacular from the water. As you sail, a selection of curated local delicacies and fine wines will be served, elevating the experience to something special.

The Voyage Itself

The boat’s spacious deck allows everyone to find a comfy spot—whether lounging in the sun or enjoying the shade with a good book. Reviewers mention the beauty of the cruising experience, often highlighting the peaceful rhythm of the waves and the joy of simply being out at sea.

The crew is praised for their personalized service, making sure drinks, snacks, and seating arrangements suit your preferences. The breakfast on board is described as leisurely, giving you time to watch the changing scenery as morning turns to afternoon.

Swimming at Magganari Beach

One of the day’s highlights is the stop at Magganari Beach—a tranquil stretch of golden sand with crystal-clear waters. Guests report it’s a perfect spot for a refreshing swim, sunbathing, or just unwinding in a serene setting. The shallow waters make it accessible for all, including non-swimmers who want to float and soak up the sun.

Exploring Ios

After several hours of sailing, you’ll arrive at Ios, known for its lively nightlife and scenic charm. But during this tour, the focus is on relaxing and exploring at your own pace. You might choose to lounge at the beach, wander through its quiet villages, or take a stroll through the whitewashed streets of Chora.

Guests appreciate the freedom to choose how to spend your time, with approximately seven hours on the island. Many mention enjoying the local vibe—relaxed, friendly, and less crowded than Santorini—making it the perfect balance for a day of exploration and downtime.

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Dinner & Night on the Boat

As the sun sets, the boat transforms into a cozy retreat under the stars. The crew prepares curated local dishes and more fine wine for dinner. Guests note how the atmosphere shifts into something intimate and memorable, with many enjoying the stargazing from the deck. The boat’s cabins are described as comfortable, providing a good night’s sleep after a day of adventures.

Returning to Santorini

The next morning, after a leisurely breakfast, the sailboat begins its journey back to Santorini. The morning views are just as stunning, with the rising sun casting a warm glow over the caldera. Many reviewers find this return leg a perfect time to reflect on their trip and enjoy the peaceful seascape one last time.

Is This Tour Worth the Price?

While $3,952 might seem substantial, it’s important to consider what’s included: privately chartered comfort, meals, wine, and the entire experience of sailing through some of Greece’s most iconic waters. The small group size (up to 6 people) ensures a more personal, intimate journey that larger tours often can’t match.

Guests frequently praise the quality of the food and wine, noting that the local delicacies served on board elevate the experience. The luxury cabins offer a comfortable retreat after days exploring islands, and the customized service helps make the experience feel exclusive.

One reviewer sums it up: “This isn’t just a boat trip; it’s a luxurious escape that combines stunning scenery, delicious food, and genuine relaxation.” If you’re craving a unique, hassle-free way to see the Cyclades with a touch of elegance, this sailing tour delivers.

Practical Details & Tips

• Duration & Starting Times: The tour lasts two days, but start times vary—check availability.
• Group Size & Privacy: It’s a private group experience, perfect for those who prefer a more intimate setting.
• What to Bring: Comfortable shoes, hat, swimwear, towel, camera, and sunscreen are recommended.
• Weather & Seasickness: Check the forecast and consider motion sickness prevention if you’re prone—sailing adds a breeze but can be choppy.
• Not Suitable for: Non-swimmers or those sensitive to seasickness, but the shallow waters at Magganari are friendly to most.

The Sum Up

This overnight sailing trip from Santorini to Ios offers a wonderfully balanced mix of scenic beauty, comfort, and local charm. The chance to relax on a private yacht with exquisite food and wine, combined with the freedom to explore Ios at your own pace, makes it a memorable choice for those wanting a more personal Greek island experience.

It’s ideal for travelers seeking tranquility, intimate settings, and a touch of luxury. While the price tag is higher, the exclusivity, quality of service, and stunning scenery justify it for anyone looking to indulge in a refined island adventure.

If you love sailing, picturesque landscapes, and authentic Greek touches, this trip will leave you relaxed, inspired, and with plenty of stories to tell.

FAQ

• How many people are in the group?

It’s a private group experience for up to 6 people, ensuring personalized attention.

• What’s included in the price?

The price covers an overnight stay in comfortable cabins, curated local delicacies, fine wine, and a leisurely breakfast on board.

• Is this tour suitable for non-swimmers?

While swimming at Magganari Beach is a highlight, non-swimmers can still enjoy the scenery and relaxing boat experience. However, safety around water is essential.

• Can I cancel if my plans change?

Yes, cancellations are free up to 24 hours before the tour, providing flexibility for your travel plans.

• What should I bring?

Comfortable shoes, a hat, swimwear, towel, camera, and sunscreen are recommended for comfort and safety.

• Are there any restrictions on smoking?

Smoking is not allowed on the boat, maintaining a clean and comfortable environment for all guests.

• Is the boat air-conditioned?

The review details focus on cabins and deck comfort, but it’s likely the cabins provide a cool resting spot—check with the provider if climate control is a priority.

• Do I need to prepare for seasickness?

If prone, consider motion sickness prevention, especially since it’s a sailing adventure across open waters.

• What’s the best time of year for this trip?

While specific dates aren’t mentioned, the weather in Greece from spring to early fall typically offers the best sailing conditions. Always check the weather forecast before booking.

• How long do I have on Ios?

You’ll have approximately seven hours on the island, enough to relax on the beach or explore at your pace.

This sailing trip truly captures the spirit of exploring Greece’s Cyclades with comfort and style. Whether you’re celebrating a special occasion or just want a unique adventure, it’s an experience that promises stunning views, delicious food, and plenty of time to unwind.

You can check if your dates are available here: