Santorini: Catamaran Cruise, Winery, & Oia Sunset Combo Tour

This full-day adventure in Santorini offers a mix of sailing, wine tasting, and sunset viewing, perfect for travelers wanting a well-rounded taste of the island’s highlights. For around $203 per person, you get a 10-hour experience that includes a 5-hour catamaran cruise, visits to renowned wineries, and a sunset finale in the picturesque village of Oia.

What we appreciate most about this tour are the stunning views of the caldera and volcanic islands that come with the boat ride, as well as the chance to indulge in Santorini’s celebrated wines right at the source. The informative guides at both the winery stops help deepen your appreciation for local winemaking traditions, and the Oia sunset at the old castle ruins provides that iconic, postcard-perfect ending.

A key consideration is that this is a bundle tour—meaning you’ll spend part of your day on the water, then switch to a coach for land-based experiences. If you’re someone who prefers a more relaxed, single-focus day, this multi-part approach could mean some waiting time or a bus transfer that interrupts the flow.

This tour is ideal for travelers who love diverse experiences—from sailing to wine tasting to strolling charming villages—and who are comfortable with a full, energetic day. It’s especially suited to those who want a balanced mix of adventure, relaxation, and scenic beauty.

You can check availability for your dates here:

Key Points

All-in-one experience: Combines a catamaran cruise, winery visits, and sunset viewing in Oia.
Authentic boat experience: A 5-hour cruise around Santorini’s volcanic islands with swimming, snorkeling, and a homemade barbecue.
Wine lovers’ delight: Visits to Venetsanos Winery and the Wine Museum offer tastings of volcanic white wines and local specialties.
Iconic sunset: Watching the sun set over the old castle ruins in Oia is a highlight, offering postcard-perfect views.
Value for money: For $203, you receive an immersive day with transportation, meals, wine, Wi-Fi, and guided insights.
Some waiting involved: The tour involves a bus transfer between activities, which could mean some downtime.

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An In-Depth Look at the Tour Experience

The Morning Catamaran Cruise: Sailing Santorini’s Caldera

The day begins with hotel pickup, which is convenient and hassle-free, ensuring you don’t have to worry about transportation. Once aboard the catamaran, you’ll find yourself gliding across the caldera, soaking in views that are truly among the most striking in Greece.

Expect a relaxed atmosphere—the vessel is spacious enough for comfort, and the crew makes a point to keep the mood lively yet laid-back. The cruise lasts about five hours, during which you’ll visit volcanic islands, swim in crystal-clear waters, and snorkel with provided equipment. The highlight for many is the chance to cool off in the hot springs or relax on Red and White Beaches—their unique colors and volcanic origins make them unlike any other beaches you’ve visited.

What stands out here is the onboard barbecue, which is surprisingly good for a boat meal—grilled chicken or pork skewers, stuffed vine leaves, roasted vegetables, and a Greek salad. Accompanying this feast are unlimited Santorinian white wine and soft drinks, making the meal both authentic and refreshing. Several reviews, like Jessica’s, mention the delicious lunch and the crew’s hospitality as a real plus.

The Winery Visits: Savoring Santorini’s Unique Wines

After returning to port, the tour takes you to two different wineries on the island, offering a deep dive into Santorini’s distinctive wine culture. The first stop is Venetsanos Winery, where you can taste three different wines while gazing over the volcano—a truly memorable setting. The next is the Wine Museum in Mesa Gonia, known for its long family tradition and volcanic white wines, including the island’s famous dessert wine.

Guests consistently praise the knowledgeable guides, like Jessica’s mention of her guide making the tour feel like a “family experience.” The focus on local volcanic white wines and the opportunity to taste desert wine adds a special touch, especially if you’re a wine enthusiast.

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The Oia Sunset: End with a View

The final part of the day is a visit to Oia, the village famous for its cascading white buildings and blue-domed churches. You’ll have some free time to wander, shop, or grab a drink at the Sun Spirit Bar, one of the best spots to watch the sunset. As the sun dips into the Aegean, you’ll understand why Oia sunsets are a bucket-list experience.

Amy’s review reflects the disappointment some travelers feel if the weather changes or if they miss out on part of the day. However, most visitors find the sunset at Oia a highlight worth waiting for, and the combination with wine and scenic views makes for a memorable final act.

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Transportation and Logistics

This tour includes round-trip hotel transfers, making logistics straightforward. The pick-up begins earlier than the starting time, so punctuality is key. The tour features a live English-speaking guide for the cruise and a bilingual guide for the land portion, ensuring you understand each part of the day.

Since this is a bundle experience, you’ll spend part of the day on the boat, then switch to a bus for the winery visits and Oia. Expect some waiting time between activities, which is typical in such full-day tours but worth noting if you prefer a more continuous experience.

What to Bring

Travelers should pack essentials like passport, swimsuit and towel, sunscreen, and sunglasses. Comfortable shoes are advisable for walking around Oia and the wineries. Wi-Fi is included, which can be handy if you want to share photos or check your emails.

Price & Value

At $203, this tour offers a comprehensive package: transportation, meals, wine tastings, snorkeling equipment, and Wi-Fi. Considering the full day of activities and the scenic beauty, it provides good value—especially for those who want a little of everything in one trip.

Who This Tour Is Best For

This experience suits travelers who enjoy variety—from sailing to wine tasting to scenic walking. If you’re someone who appreciates authentic local experiences and doesn’t mind a busy schedule, you’ll find this tour rewarding. However, if you prefer a more relaxed, slower-paced day, this might feel a bit rushed, especially with the bus transfers and scheduled stops.

It’s also a great choice for first-time visitors to Santorini wanting a guided overview of the island’s highlights, with the safety net of transportation and organized activities. Wine lovers, in particular, will enjoy the tasting stops, especially given the insightful guides.

The Sum Up

This Santorini combo tour offers a well-rounded day packed with memorable moments. The catamaran cruise takes you through volcanic waters, providing stunning scenery and the chance to swim in hot springs. The wine tasting stops deepen your appreciation for the island’s unique volcanic terroir, and the sunset in Oia is the perfect, iconic finish.

While some might find the full schedule a bit intense, most will appreciate the diversity of experiences and the ease of organized transportation and guided commentary. The value for the price is solid, given the inclusions of meals, wine, and Wi-Fi—especially if you want a comprehensive taste of Santorini’s natural beauty and local flavors.

This tour is best suited for active travelers who enjoy variety, scenic boat rides, and authentic wine experiences. If you’re seeking a full day of sightseeing without the hassle of planning each step, it’s a practical, enjoyable choice.

FAQ

Is hotel pickup included?
Yes, the tour includes round-trip transfers from your hotel or the nearest accessible point, making logistics simple.

What should I bring?
Bring your passport, swimwear, towel, sunscreen, and comfortable shoes. Wi-Fi is available onboard, which can be convenient for sharing your experience.

How long is the boat cruise?
The cruise itself lasts about five hours, during which you can swim, snorkel, and enjoy the barbecue meal onboard.

Can I customize the sunset experience?
The sunset viewing at Oia is scheduled as part of the tour; you’ll have some free time to explore or relax at the Sun Spirit Bar.

Are drinks included?
Yes, unlimited Santorinian white wine and soft drinks are included during the cruise and at the winery stops.

Is there any vegetarian meal option?
Yes, a vegetarian meal of stuffed vine leaves, roasted vegetables, and salad is available.

What if the weather is bad?
Weather can affect the cruise; the tour allows free cancellation up to 24 hours in advance, so you can reschedule or get a full refund if conditions aren’t suitable.

This tour balances scenic sailing, authentic wine, and sunset magic, making it a strong choice for travelers wanting to experience several of Santorini’s highlights in one well-organized day.