Sail through Santorini’s stunning caldera while indulging in a wine tasting experience on a private sailboat. Discover the island’s renowned wines with a sommelier and enjoy breathtaking views. Daytime and sunset options available.
Sail through Santorini’s stunning caldera while indulging in a wine tasting experience on a private sailboat. Discover the island’s renowned wines with a sommelier and enjoy breathtaking views. Daytime and sunset options available.
- Vlychada - Get ready to embark on a private 5-hour cruise departing from Vlychada Marina.
- Red Beach - Sail past Santorini’s most famous beach, where you’ll pause briefly to capture photos of the stunning, colorful volcanic landscape from the water.
- White Beach - Glide by the breathtaking White Beach, accessible only by boat, a…
- Vlychada - Get ready to embark on a private 5-hour cruise departing from Vlychada Marina.
- Red Beach - Sail past Santorini’s most famous beach, where you’ll pause briefly to capture photos of the stunning, colorful volcanic landscape from the water.
- White Beach - Glide by the breathtaking White Beach, accessible only by boat, a remarkable result of massive volcanic eruptions.
- Aspronisi - Along the way, observe the naturally sculpted Indian face on a black rock before entering Santorini’s caldera, where a picturesque lighthouse sits atop the cliff on the right. On the left, see the remnants of an eruption, the pumice island of Aspronisi.
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Santorini Volcano - Sail between the two volcanoes (Palaia & Nea Kameni) and approach the sulfuric warm waters of the hot springs.
Note: We typically do not stop for swimming due to overcrowding and potential damage to swimwear from sulfur. Additionally, we do not visit the volcano itself, but enjoy the cruise. - Thirassia - Enjoy a swim in the tranquil, crystal-clear waters of Thirassia Island and savor a delicious meal prepared on board, while admiring the eastward view of the caldera. Witness the magnificent Santorini sunset from the boat.
- Vlychada - After the stunning sunset, return to Vlychada Marina, where your transfer will be ready to take you back to your original pickup location.
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Santorini - Travel time between attractions is included, with the total tour duration, including pickup and drop-off, being approximately 6 hours.
- Most wine tasting occurs in Thirassia for safety, but you’ll have enjoyed two wines by then.
- The tasting features dry whites, a rosé, a dry red, and the renowned dessert wine, Vinsanto.
- Choose a sunset cruise to enjoy the sunset on board.*

- Private Sailing cruise on a 44-ft sail boat
- Wine tasting of 6-glasses of Santorini wine
- English-speaking certified wine guide/sommelier by WSET
- Dinner
- Use of snorkeling equipment
- Hotel/port/airport pickup and drop-off
- All Fees and Taxes
- Free WiFi
- Drinks & Beverages
- Towels & Jackets (to be returned to the crew)
- Private Sailing cruise on a 44-ft sail boat
- Wine tasting of 6-glasses of Santorini wine
- English-speaking certified wine guide/sommelier by WSET
- Dinner
- Use of snorkeling equipment
- Hotel/port/airport pickup and drop-off
- All Fees and Taxes
- Free WiFi
- Drinks & Beverages
- Towels & Jackets (to be returned to the crew)
- Personal expenses & gratuities (optional)
- Personal expenses & gratuities (optional)
Experience a one-of-a-kind Santorini sailing tour while sipping some of the island’s best wines! Learn about Santorini wines while tasting 6 glasses of different Santorini wines such as Assyrtiko, Nychteri, Vinsanto, and others while sailing through the unique caldera! Choose between a daytime and a sunset cruise. Transfers, drinks and meals are…
Experience a one-of-a-kind Santorini sailing tour while sipping some of the island’s best wines! Learn about Santorini wines while tasting 6 glasses of different Santorini wines such as Assyrtiko, Nychteri, Vinsanto, and others while sailing through the unique caldera! Choose between a daytime and a sunset cruise. Transfers, drinks and meals are included.
- Travel time between attractions are included in the total tour duration.
- Individuals under the age of 18 are not allowed to consume alcohol under Greek law.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.