Sailing from Oia offers travelers the best vantage point to experience Santorini’s dramatic caldera and volcanic landscape.
Two standout options deserve special mention: The 5-hour private catamaran cruise packs tremendous value, combining swimming stops at volcanic hot springs with a sunset viewing and an authentic Greek buffet spread.
I’m especially fond of the traditional sailing experience with Cycladica – their 5-hour trip feels more intimate, and the homemade pies and local snacks add a wonderfully personal touch.
Both tours include snorkeling gear and drinks.
Let’s look at our favorite sailing tours from Oia…
Key Points
- The Oia: Private Santorini Catamaran Tour for Two offers a romantic 5-hour private sailing experience with a delicious meal and unlimited drinks.
- The Santorini: Kymatia Traditional Sailboat Tour by Cycladica provides a transformative 5-hour sailing adventure with photo stops, swimming, and a 2-hour sunset experience.
- The Private Catamaran Excursion With Food and Drinks offers a customizable 5-hour tour with a Greek buffet, unlimited drinks, and the opportunity to spot dolphins or seals.
- The Santorini Full Day Catamaran Excursion – Gold Package is a 10-hour private tour with a customizable itinerary, swimming in thermal volcanic waters, and a Santorinian buffet.
- The sailing experiences in Oia provide a range of options, from romantic couples’ tours to larger group excursions, all offering stunning views, activities, and local cuisine.
Santorini: Full Day Catamaran Excursion With Food & Drinks
For those seeking a truly immersive Santorini experience, the Santorini Full Day Catamaran Excursion – Gold Package offers a captivating blend of adventure, relaxation, and culinary delight.
Priced at €2,200 for up to 8 participants, this 10-hour private catamaran tour allows you to customize your itinerary with the captain, exploring hidden gems, swimming in thermal volcanic waters, and snorkeling in crystal-clear seas.
The onboard amenities are equally impressive, featuring a delicious Santorinian buffet with barbecue chicken, shrimps, and vegetarian options, as well as unlimited drinks including beer, wine, and soft drinks.
Complimentary transportation, safety equipment, and a compact map with updated island information are also included.
Whether you’re looking to soak up the sun, spot dolphins or seals, or simply unwind, this catamaran excursion promises an unforgettable day on the Aegean Sea.
Read our full review: Santorini: Full Day Catamaran Excursion With Food & Drinks Review
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Santorini: Private Catamaran Excursion With Food and Drinks
The Santorini: Private Catamaran Excursion with Food and Drinks offers an exclusive and customizable nautical adventure on the Aegean Sea. Priced from $1,165.58 for a group of up to 4, this 5-hour tour provides the flexibility to tailor the itinerary based on preferences and weather conditions.
Guests can swim in thermal volcanic waters, snorkel in crystal-clear seas, and may even spot dolphins or seals.
The catamaran is equipped with a Greek buffet, including a Santorinian salad, local dips, grilled chicken, shrimp, and vegan options. Unlimited drinks, such as water, soft drinks, local wine, and beer, are also included.
Snorkeling gear, life jackets, blankets, and towels are provided, along with free Wi-Fi, a compact map, and a safety briefing.
Rated 4.9/5 based on 24 reviews, the tour emphasizes customer-centric service, with the manager Irene ensuring a seamless experience.
Travelers highlight the crew’s helpfulness and flexibility, as well as the enjoyable food and swimming spots.
Read our full review: Santorini: Private Catamaran Excursion With Food and Drinks Review
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Oia: Private Santorini Catamaran Tour for Two With Drinks
Offering a more intimate nautical adventure than the Santorini: Private Catamaran Excursion, the Oia: Private Santorini Catamaran Tour for Two With Drinks invites couples to explore the breathtaking caldera and coastline of Santorini from the comfort of a private catamaran.
This 5-hour tour includes pickup from your hotel, a delicious meal, and unlimited drinks, allowing you to fully immerse yourselves in the stunning scenery.
With a maximum of two passengers, this private tour provides a personalized experience, perfect for couples seeking a romantic and exclusive way to discover Santorini’s natural wonders.
Highlights include swimming in the volcanic hot springs, visiting secluded beaches, and witnessing the famous Santorini sunset from the water.
At €130.00 per person, this tour offers exceptional value, making it an ideal choice for couples looking to create lasting memories on their Santorini getaway.
Read our full review: Oia: Private Santorini Catamaran Tour for Two With Drinks Review
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Santorini: Kymatia Traditional Sailboat Tour by Cycladica
Aboard a meticulously restored 50 ft wooden traditional sailboat, the Santorini: Kymatia Traditional Sailboat Tour by Cycladica invites travelers to embark on a transformative 5-hour adventure. Priced at $1,536.44 for up to 9 participants, this tour offers a flexible booking option with the ability to cancel up to 24 hours in advance for a full refund.
The experience begins with a black cab transfer from Thera, followed by a 20-minute water transfer to the sailboat. Guests will then enjoy 3 hours of sailing, a break, a photo stop, a visit, wine, a guided tour, swimming, and local snacks, culminating in a 2-hour sunset experience.
Along the way, they’ll have the opportunity to explore Santorini and neighboring islands, with customizable off-grid experiences to reconnect with nature. The onboard experience emphasizes slow living and unhurried exploration, with curated snacks and homemade pies included.
The crew provides a safety briefing and snorkeling equipment, making this tour unsuitable for participants over 70 years old. Beachwear is recommended, and the host or greeter speaks English.
Read our full review: Santorini: Kymatia Traditional Sailboat Tour by Cycladica Review
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The Sum Up
Santorini’s Oia offers a range of exceptional sailing experiences. From full-day catamaran excursions with food and drinks to private sailboat tours for two, there’s something for every traveler. Explore the island’s stunning coastline, swim in crystal-clear waters, and savor local delicacies – all while taking in the breathtaking views. Whether you’re a sailing enthusiast or simply seeking a unique adventure, Oia’s sailing options provide an unforgettable way to experience the beauty of Santorini.