Santorini: Ios Island Overnight Sailing Trip with Meals

Santorini: Ios Island Overnight Sailing Trip with Meals — An Authentic Greek Sea Adventure

Imagine sailing across the shimmering waters of the South Aegean, feeling the gentle push of the wind as you glide toward the island of Ios. For just over $4,000 for a group of up to six, you’ll spend a night aboard the elegant Kymatia Sailboat, enjoying the blend of comfort, adventure, and genuine Greek charm. This trip is designed for those who crave a taste of luxury combined with authentic island life — perfect for couples, friends, or families wanting to celebrate with a unique experience.

We love the way this tour combines luxury sailing with active exploration. The spacious decks are ideal for soaking up the sun and watching the volcanic cliffs coast past, while the overnight stay in comfortable cabins ensures you sleep peacefully after a day of swimming and sightseeing. The delicious meals served on board, including curated local delicacies and fine wine, elevate the journey from simple boat trip to a true indulgence.

A possible consideration is that this experience isn’t suited for everyone — especially those prone to seasickness or non-swimmers. The sailing can be smooth, but if you’re sensitive to motion or dislike being on the water overnight, it might require some planning.

This trip is best suited for travelers looking for a luxurious, scenic escape that combines sailing, fine dining, and island discovery. If you’re eager to see Ios from a different perspective — on the water — and enjoy a more intimate, personalized experience, this trip could be a highlight of your Greek adventure.

Key Points

• Luxury and Comfort: Overnight in well-appointed cabins with personalized service.
• Scenic Sailing: Cruise past volcanic cliffs and stunning coastline with ample time to relax outdoors.
• Gourmet Meals and Drinks: Enjoy curated local dishes and fine wine on board.
• Island Experience: Once on Ios, you get about seven hours to explore beaches, charming town streets, and natural beauty.
• Swimming at Magganari Beach: Perfect for a refreshing swim in crystal-clear waters.
• Flexible & Convenient: Book now, pay later, and cancel up to 24 hours beforehand with no penalty.

You can check availability for your dates here:

A Closer Look at the Sailing Adventure

When we picture a Greek island getaway, we often think of sunny beaches and vibrant tavernas. This trip, however, offers a different view — one from the deck of a luxury sailboat. Starting in Santorini, the boat, Kymatia, sets sail with a dedicated crew at the helm. As you leave the iconic caldera behind, you’ll enjoy panoramic views of volcanic landscapes, whitewashed buildings, and the endless blue of the Aegean.

The journey itself is a balance of relaxation and activity. The deck is spacious enough to stretch out, sip on fine wine, or snap photos of the passing scenery. We loved the way the crew curates local delicacies, making each meal a small celebration, paired perfectly with Greek wines. The gentle motion of the boat, combined with the soothing sound of waves, creates a calming atmosphere — a true escape from busy daily life.

Overnight accommodation on the boat is surprisingly comfortable, with cozy cabins that provide a peaceful retreat after a day in the sun. Reviewers often mention how well-organized and attentive the crew is, preparing everything from evening meals to breakfast in the morning. You’ll wake up refreshed, enjoying a leisurely breakfast as the boat gently floats toward Ios.

Arriving at Ios is where the adventure begins. The island’s highlight is Magganari Beach — described as a “serene paradise” with golden sands and crystal-clear waters, perfect for swimming. Since the waters are shallow and calm, it’s suitable for all visitors, including families and those less confident swimmers. One reviewer mentioned, “The water at Magganari Beach was perfect for a swim, and I loved the peaceful vibe.”

Exploring Ios on your own gives you around seven hours to soak up its charm. The island’s traditional whitewashed houses, cobblestone streets, and laid-back beaches make it easy to wander or lounge. For those who enjoy a lively scene, Ios’s famous nightlife is within reach, though you might prefer to relax at the tranquil beaches or stroll through the quiet villages.

In the evening, you can relax back on the boat, enjoying stargazing from the deck or simply soaking up the peaceful ambiance. The return trip to Santorini in the morning offers one last chance to enjoy the view, along with a leisurely breakfast on board.

What’s Included and What to Consider

This experience includes an overnight stay in a comfortable cabin, curated local delicacies, fine wine, and a casual breakfast. The personalized service from the crew is often praised, making the trip feel intimate and catered to your comfort.

You’ll want to bring comfortable shoes, a hat, swimwear, towel, camera, and sunscreen — essentials for beach days and sightseeing. Keep in mind that smoking isn’t allowed onboard, which helps maintain a pleasant environment for everyone.

To make the most of your trip, it’s advisable to check the weather forecast and prepare accordingly. Guests prone to seasickness should consider bringing motion sickness prevention, as the boat is active at sea, especially overnight.

Why This Trip Stands Out

Many travelers highlight stunning views and the quality of the wine as major perks. The chance to watch the sunset from the deck, with a glass of local wine in hand, is a moment many remember fondly. The delicious meals prepared on board elevate the experience, turning a boat ride into a culinary delight.

In terms of value, this journey offers more than just transportation — it’s an all-in-one experience with scenic sailing, authentic meals, and a peaceful overnight stay, making it a worthwhile splurge for those who appreciate comfort and exclusivity.

Possible Drawbacks

The main consideration is the cost — at over $4,000 for a group of six, it’s not the most budget-friendly option. However, for the level of comfort, personalized service, and unique experience provided, many travelers find it well worth the expense. Also, those who dislike being at sea overnight or have trouble with seasickness may find it less enjoyable, so planning ahead is key.

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Who Should Consider This?

This tour appeals most to adventurous travelers and lovers of the sea who want a luxurious, intimate way to see Ios. If you’re looking for a romantic getaway, a special celebration, or simply a different perspective on the Greek islands, this sailing trip fits perfectly.

FAQs

Is this tour suitable for non-swimmers?
While swimming at Magganari Beach is optional, non-swimmers should be aware that there will be opportunities to swim in the clear waters. If you’re not comfortable in the water, you can relax on the boat and enjoy the scenery.

How many people are on the boat?
The trip is designed for groups of up to six people, making it a more intimate and personalized experience compared to larger tours.

What’s the cancellation policy?
You can cancel up to 24 hours in advance for a full refund, providing flexibility if your plans change.

Do I need to bring my passport or ID?
Yes, you’ll need a valid ID or passport for check-in, especially for international travel within Greece.

Are meals included?
Yes, the package includes dinner on the boat, breakfast the next morning, and curated local delicacies paired with fine wine.

Is there a dress code?
Dress comfortably — bring casual clothes, a hat, and sunscreen for daytime, and consider a light jacket if you plan to be on deck after sunset.

Final Words

This overnight sailing tour from Santorini to Ios blends the best of Greek island life with the luxury of sailing. You’ll wake up in a different world, surrounded by natural beauty — a perfect way to indulge your senses and create lasting memories. If you’re after an authentic, relaxed, and scenic experience that combines the sea, good food, and small-group intimacy, this trip is well worth considering.

Ideal for those who want a break from the crowds and crave genuine connections with the stunning landscape and local culture, this adventure promises a mix of tranquility, excitement, and comfort that few other experiences can match.

You can check availability for your dates here: