Oia is one of the most picturesque spots in Santorini, famous for its stunning sunsets, whitewashed buildings, and breathtaking caldera views. But what truly makes Oia shine are its sailing experiences — a perfect way to see the island from the water, admire volcanic landscapes, and enjoy some well-deserved relaxation. Whether you’re celebrating a special occasion or just want a peaceful day on the sea, Oia offers a variety of boat trips that stand out. For example, the Private All-In Catamaran Cruise tops our list with its personalized approach and excellent reviews, making it ideal for those seeking intimacy and flexibility in their sailing adventure.
What sets these tours apart is their focus on authentic experiences—snorkeling, hot springs, local food, and stunning scenery. Many include options to customize your route or add special touches like a romantic proposal. We’ve picked a diverse lineup to match different tastes and budgets, from exclusive private charters to lively group excursions. Read on to find out which match fits your style.
1. Santorini: Private All-In Catamaran Cruise, with Food|Drinks
Enjoy a private, tailor-made day or sunset cruise around Santorini’s most scenic waters. This cruise is ideal if you want a personalized experience—sail through the caldera, stop at volcanic hot springs, and snorkel in clear waters. The boat is fully equipped with a BBQ meal, local wines, beers, and soft drinks, making it a perfect way to indulge while taking in the views.
What makes this cruise shine is its ability to adapt to your preferences. You can choose to swim in volcanic waters, relax on deck, or snap photos of the iconic red and white beaches. The itinerary includes a safety briefing at Vlychada Port, stops at Red and White Beaches, and a longer session at Nea Kameni Hot Springs with swimming, snorkeling, and a delicious onboard meal. Reviewers love the crew’s helpful attitude and the flexibility—one even calls it the “best birthday cruise ever.” Given the 5-hour duration and exclusive nature, this cruise delivers a memorable and luxurious experience for up to 6 people.
Bottom Line: Perfect for couples or small groups seeking privacy, great food, and customizable routes in an intimate setting.
2. Santorini: Luxury Catamaran Cruise with Lunch, BBQ & Drinks
For those wanting a more upscale experience, this Luxury Catamaran Day Cruise offers a well-rounded package. Departing from multiple pickup points, the small group heads to explore Santorini’s coastline, with stops at Red Beach, White Beach, and Palea Kameni Hot Springs for swimming and snorkeling. The highlight is the onboard Greek buffet, with a BBQ featuring grilled seafood and local wines, all served in a relaxed atmosphere.
What distinguishes this cruise is its focus on comfort and scenic beauty. You’ll sail past the Indian Rocks and Venetian Lighthouse, enjoying the views from the deck, and indulge in a traditional lunch with drinks at Thirasia Island. The reviews praise the crew’s friendly service and the overall relaxing vibe—many refer to it as a “great experience” that’s both fun and laid-back. The itinerary is full of photo opportunities, and the hot springs provide a chance for a therapeutic dip.
Bottom Line: Best suited for travelers who appreciate a mix of comfort, good food, and scenic sailing with a small group.
3. Santorini: Full-Day Catamaran Cruise, with Food|Drinks
If you’re in Santorini for a full day and want to really immerse yourself, this 10-hour full-day cruise is the way to go. It’s ideal for those who want a comprehensive experience—sailing past cliffs and caves, swimming in crystal waters at spots like Palea Kameni, and enjoying a BBQ feast onboard, complete with seafood and Greek yogurt with honey.
This cruise offers a flexible itinerary that includes stops at the volcanic hot springs, the red and white beaches, and Thirasia Island. The boat is equipped with sunbeds and snorkeling gear, perfect for relaxing or exploring underwater. Reviewers note that the long duration allows for plenty of swimming and sightseeing, making it a good value for those wanting a full day on the water. Plus, the onboard meal and drinks receive high praise.
Bottom Line: Great for active travelers who want a full day of swimming, sightseeing, and excellent food, with the convenience of a flexible itinerary.
4. SANTORINI PRIVATE SAILING CRUISE TOUR
This private sailing tour offers a highly personalized experience for up to 2 people at a price of $1,355 per group. It’s perfect if you’re celebrating a romantic occasion like a honeymoon or proposal. The cruise takes you around the volcanic caldera, providing intimate moments with your partner or close friends.
The tour includes a private catamaran, good food, and drinks, tailored to your preferences. Some guests have used it for special events—like a surprise proposal—because the captain and crew are very accommodating. The reviews highlight the exclusivity and the beautiful, peaceful setting. It’s an ideal choice for travelers wanting privacy, a romantic vibe, and a flexible schedule.
Bottom Line: Best suited for couples or small groups seeking a private, romantic cruise with personalized touches.
How to Choose the Best Sailing Experience in Oia
When selecting a sailing tour, think about your priorities: budget, group size, desired activities, and special occasions. If you want a private experience, the Private All-In Catamaran Cruise is unmatched for intimacy and flexibility. For a touch of luxury with family or friends, the Luxury Catamaran Cruise offers comfort and scenic beauty. Those wanting a longer, full-day adventure should consider the Full-Day Cruise, perfect for active explorers.
For a highly exclusive and romantic experience, the Private Sailing Cruise is a perfect choice, especially if celebrating something special. Booking early is advised, especially in peak summer months, as these tours fill quickly.
Final Thoughts
Oia’s sailing experiences cater to a variety of tastes—whether you prefer private, romantic moments or lively group excursions. The Santorini private all-in catamaran and luxury cruise stand out for their high ratings and excellent reviews, offering comfort, flexibility, and thoughtful itineraries. For longer, more immersive days, the full-day cruise provides excellent value.
No matter which you choose, a sailing experience is one of the best ways to see Santorini’s stunning coastlines and volcanic features. Book early, bring your camera, and prepare for a memorable day on the water—just don’t forget your swimsuit.