Sailing from Oia offers the best vantage point to experience Santorini’s dramatic coastline and famous caldera. Local operators run half-day and full-day tours on both traditional wooden vessels and modern catamarans, with departures timed for sunset or daytime exploration.
My favorite trips include the 5-hour sunset catamaran cruise (great food, uncrowded deck space) and the traditional wooden sailboat tour (authentic feel, excellent value). The volcanic beach stops and hot springs add geological interest to these seafaring adventures.
For families and groups, private charters provide flexibility and personalized service. Let’s explore the top-rated sailing tours from Oia.
Key Points
- The Kymatia Traditional Sailboat Tour offers a 5-hour excursion with 3 hours of sailing and a break for swimming, snacks, and sunset viewing.
- The Private Catamaran Excursion with Food and Drinks provides a 5-hour all-inclusive tour with activities like exploring volcanic beaches and snorkeling.
- The Full Day Catamaran Excursion with Food & Drinks is a 10-hour private gold package that includes highlights like the Red Beach and Santorini Lighthouse.
- The Private Santorini Catamaran Tour for Two with Drinks is a 5-6 hour private tour featuring an open bar, a delectable meal, and breathtaking views.
- These sailing experiences in Oia offer personalized, high-quality services with amenities like hotel transfers, snorkeling gear, and Wi-Fi, catering to diverse preferences.
Santorini: Kymatia Traditional Sailboat Tour by Cycladica
For a quintessential Santorini sailing experience, consider the Kymatia Traditional Sailboat Tour by Cycladica. This 5-hour excursion allows you to explore the island’s stunning caldera aboard a 50ft wooden sailboat.
The tour kicks off with a 1-hour black cab transfer to the departure point in Thera, followed by a 20-minute water transfer to the boat. Once aboard, you’ll sail for 3 hours, taking in the breathtaking views of the caldera.
During the 2-hour break, you’ll have the chance to swim, enjoy local snacks and wine, and witness a stunning sunset. The tour is priced at $1,528.86 per group (up to 9 participants) and features a range of amenities, including snorkeling gear, onboard refreshments, and an English-speaking host.
Keep in mind that this tour isn’t suitable for those over 70 years of age. For a unique and relaxing way to experience Santorini, the Kymatia Traditional Sailboat Tour is a must-consider option.
Read our full review: Santorini: Kymatia Traditional Sailboat Tour by Cycladica Review
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Santorini: Private Catamaran Excursion With Food and Drinks
Seeking a more private and customizable sailing adventure in Santorini? Consider the Private Catamaran Excursion With Food and Drinks.
This all-inclusive day or sunset tour offers a personalized experience for up to 4 guests at $1,159.83 for the group. Over 5 captivating hours, you’ll explore Santorini’s volcanic beaches, spot dolphins and seals, and snorkel in the crystal-clear waters teeming with vibrant marine life.
Sail between lava islands and enjoy the thermal waters of the volcano. Indulge in freshly prepared Greek cuisine and refreshing drinks as you take in the scenic vistas and historical insights.
The tour includes complimentary hotel transfers, snorkeling gear, and amenities like Wi-Fi and shaded areas. While there are no medical facilities or lifeguards on board, the crew prioritizes safety.
With an impressive 4.9/5 rating from 24 reviews, this private catamaran excursion promises an unforgettable and personalized sailing adventure in Santorini.
Read our full review: Santorini: Private Catamaran Excursion With Food and Drinks Review
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Santorini: Full Day Catamaran Excursion With Food & Drinks
Embarking on a full-day catamaran excursion, you’ll explore Santorini’s captivating landscapes and crystal-clear waters. Priced from $2,319.66 for up to 8 participants, this 10-hour private gold package offers a comprehensive experience, including free cancellation and a reserve now, pay later option.
Sail between lava islands, swim in vibrant marine life, and enjoy the thermal waters of the volcano. Savor freshly prepared Greek cuisine and drinks as you relax under the sun. Key highlights include the Red Beach, White Beach, Santorini Lighthouse, and Mesa Pigadia Beach.
While medical facilities are unavailable on board, the crew will provide safety instructions. Pregnant women can’t swim in the hot springs, and guests assume risks related to activities.
Complimentary amenities include hotel transfers, snorkeling gear, and Wi-Fi. Remember to bring your passport, swimwear, and sun protection. Alcohol, drugs, and large bags are prohibited. Gratuities for the crew are appreciated for excellent service.
Read our full review: Santorini: Full Day Catamaran Excursion With Food & Drinks Review
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Oia: Private Santorini Catamaran Tour for Two With Drinks
Sail off the beaten path on a private catamaran tour of Santorini’s stunning coastline.
Set out on a 5-6 hour journey with your special someone and enjoy an open bar, delectable meal, and breathtaking views. Cruise along the volcanic islands, stopping to swim in the rejuvenating hot springs. Soak up the sun on the spacious deck as you sail past iconic landmarks like the Venetian Lighthouse.
This luxurious experience is rated 4.7 out of 5 stars by previous travelers, who’ve praised the attentive crew and the opportunity to fully enjoy Santorini’s natural beauty.
At Kč 2,782 per person, it’s an investment, but the memories you’ll create will last a lifetime. Whether you’re celebrating a special occasion or simply seeking an unforgettable day on the water, this private catamaran tour promises an intimate and enchanting adventure.
Read our full review: Oia: Private Santorini Catamaran Tour for Two With Drinks Review
Book now: Check availability
Recap
Enjoy the best sailing experiences in Oia, Santorini. Take a traditional sailboat tour, indulge in a private catamaran excursion, or embark on a full-day catamaran adventure. Soak up the stunning views, savor delectable food and drinks, and create unforgettable memories on the sparkling Aegean Sea. Tailor your sailing experience to your preferences for an unforgettable time in this picturesque Greek island.