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Experience a private sailing cruise around Santorini’s caldera with gourmet food, drinks, and stunning views—perfect for couples or small groups seeking romance and adventure.
Imagine gliding across the shimmering waters of the Santorini caldera on a private catamaran, surrounded by spectacular volcanic scenery, with the wind in your hair and a glass of Greek wine in hand. That’s exactly what the Santorini Private Sailing Cruise offers—a tailored, intimate adventure that combines the thrill of sailing with the romance of a Greek island escape. Whether celebrating a special occasion or just craving a unique way to see Santorini, this tour promises a blend of scenic beauty, delicious food, and personalized service.
What we love most about this experience is how it balances luxury with authenticity. You’ll enjoy a private vessel that ensures your journey is exclusive, with a knowledgeable crew guiding you through Santorini’s highlights. Plus, the onboard Greek meal, paired with excellent drinks like local wine and beer, makes it feel like a special celebration. That said, it’s important to note that this cruise isn’t suitable for pregnant women, those with mobility issues, or anyone under 1 year old—so it’s best for able-bodied travelers looking for a comfortable, stylish outing.
This tour is perfect for couples seeking romance, small groups of friends wanting a memorable day out, or anyone looking for a private, flexible way to explore Santorini’s beauty. If you’re after an authentic experience with scenic vistas, good food, and a relaxed vibe, this cruise could be a highlight of your trip.


When it comes to exploring Santorini, the volcanic caldera and surrounding islands are among the top attractions—and what better way to see them than from the deck of a comfortable catamaran? This tour, provided by THIRA TOURS, is designed to deliver an elegant, private experience with plenty of highlights along the way, all wrapped in a relaxed, friendly atmosphere. And at a price of $1,355 per group (up to two), it offers a level of exclusivity and personalized service that makes it feel like a true luxury escape.
Sailing fans have several other Oia options to choose from
The cruise begins with hotel pickup and modern air-conditioned transportation, easing you into the day before the adventure even starts. Most guests are picked up about an hour prior to departure, giving you time to relax and enjoy the scenic ride to the port. Once aboard the catamaran, you’ll quickly notice the professional Greek skipper and crew, whose friendly guidance helps create a laid-back yet attentive vibe.
The route promises many of Santorini’s most iconic sights. While the boat cannot moor directly on beaches, it stops as close as possible for swimming and snorkeling—equipped with snorkeling gear so you can cool off in the crystal-clear waters. The boat will maintain a safe distance from the hot springs (about 50 meters), where the temperature difference makes for a fascinating experience. Many reviewers mention how the crew carefully balances sightseeing with comfort, providing plenty of time for relaxing on deck, taking photos, or enjoying the scenery.
One of the tour’s standout moments is when the captain anchors at a spot with a perfect view of Santorini as the light begins to soften. Here, you’ll savor a Greek meal served on board—think light-fried fish fillets, BBQ chicken, Greek salad, pasta, bread, and spreads. Travelers consistently praise the quality of the food, with comments like “the meal was surprisingly delicious and was served with plenty of local wine and beer.” The included complimentary drinks—white wine, Greek beer, sodas, and water—enhance the experience and keep everyone refreshed as the day progresses.
As the tour winds down, the sunset cruise becomes the pinnacle. When the sky turns to hues of orange and pink, you’ll be docked at a spot with what many describe as “the best view of the island.” Watching the sun dip behind Santorini’s volcanic silhouette from a private boat feels exclusive and special—a moment many travelers cherish. The crew ensures you have ample time to soak in the scenery, sip wine, and create lasting memories.

The tour includes hotel pickup and drop-off, making it hassle-free, especially if you’re staying in Fira, Oia, or Imerovigli. The skipper and crew are described as knowledgeable and friendly, often going the extra mile to ensure comfort and enjoyment. The onboard amenities—beach towels, restrooms, changing rooms, snorkeling equipment—add convenience, especially on a day that involves swimming and lounging.
Food-wise, the menu offers both vegetarian options—such as Greek salad, roasted vegetables, and rice-stuffed vine leaves—and meat dishes like fried shrimp and grilled chicken. This variety accommodates most dietary preferences, and reviewers note the meals are hearty and well-prepared.
However, for travelers with mobility issues, pregnant women, or those not comfortable on boats, this experience may not be suitable. The tour’s conditions mean it’s best enjoyed by those able to fully participate in the sailing and swimming activities.
More ways to experience Oia from the water include these boat tours
At $1,355 for a private group of up to two, this cruise isn’t inexpensive. But considering the exclusivity, personalized service, gourmet meal, and stunning scenery, many would agree it offers excellent value for a once-in-a-lifetime experience. For couples celebrating a special occasion, the privacy and romantic setting can make it a truly memorable event. Small groups also benefit from a flexible, intimate atmosphere, far removed from crowded tour boats.

If you’re after a luxurious, private way to experience Santorini’s caldera, this sailing cruise ticks many boxes. It’s perfect for couples wanting a romantic adventure, or small groups looking for a special day on the water. The inclusion of a gourmet Greek meal, good drinks, and scenic stops creates an experience that feels indulgent yet authentic.
On the flip side, if you prefer more energetic, social outings, or have mobility concerns, this might not be the best fit. The tour’s focus on privacy and comfort means it’s less about lively group activities and more about enjoying the scenery and each other’s company.
This cruise offers a blend of scenic beauty, fine food, and personalized service—making it a strong choice for those wanting a memorable, romantic, and exclusive day in Santorini.
Is this tour suitable for children?
The tour specifies it’s not suitable for babies under 1 year and generally targets adult travelers. Children over 1 might be allowed, but it’s best to check directly with THIRA TOURS.
How long is the cruise?
While the exact duration isn’t specified, it’s a one-day experience with flexible timing, including stops for swimming, lunch, and sunset viewing. Expect a full day of cruising and sightseeing.
What should I bring?
Bring your passport or ID, hat, camera, water shoes, clothes suitable for getting wet or dirty, and your travel insurance documents. Don’t forget a credit card for extras, and a pen for any paperwork.
Can I cancel if my plans change?
Yes, the tour offers free cancellation up to 24 hours in advance, making it a flexible option if your plans are uncertain.
Is vegetarian food available?
Yes, the menu includes vegetarian dishes like Greek salad, pasta with red sauce, roasted vegetables, and rice-stuffed vine leaves.
Will I get seasick?
This depends on individual sensitivity; however, the vessel is modern and stable. If you’re prone to seasickness, it’s advisable to bring medication just in case.
Are there any restrictions on alcohol consumption?
Yes, intoxication is not allowed onboard, and alcohol in the vehicle is prohibited. The included drinks are meant for consumption during the cruise in moderation.
This private sailing cruise around Santorini offers a blend of scenic beauty, gourmet food, and personalized service that appeals to travelers seeking a special, intimate experience on the water. With its well-rounded amenities and flexible options, it’s a memorable way to see the island from a unique perspective—perfect for creating your own romantic story amidst Greece’s stunning landscape.