The 9 Santorini Sailing Tours We Would Step Aboard

1.Sailing Catamaran Cruise with BBQ and Drinks

★★★★★★★★★★4.7 · 1,452 reviews · 5 hours · from $117Our pick

Spend five hours aboard a luxury catamaran from Vlychada, with hotel pickup, three swim stops, Red and White Beach views, the hot springs, volcano, and a BBQ at Mesa Pigadia. English and Greek crew members, including Maria and Neta on some departures, serve wine, soft drinks, and optional premium drinks.

“This is my second time on this tour, with the same company, and I still recommend them. Safe, fun, informative, with a great lunch and plenty of time to swim and relax while listening to music and coasting on the water.”

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2.Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

★★★★★★★★★★4.5 · 1,105 reviews · 5 hours (approx.) · from $95Best value

Spend about five hours on a spacious Santorini catamaran, with hotel pickup, caldera views, hot springs, Red Beach, White Beach, swimming, snorkeling, and a BBQ meal. Complimentary water, soft drinks, and Santorinian Nychteru wine are included. The later sailing aims for sunset near Oia, though the final viewing point can change.

“Overall it was ok. The food was good along with the views. Music was load and it could’ve been shorter. Those looking for a quiet ride around seeing the sites this is not for you.”

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3.Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 560 reviews · 5 hours (approx.) · from $145Top rated

Spend about five hours aboard a catamaran sailing around Santorini’s caldera. Swim near the Red and White Beaches, visit Palea and Nea Kameni, soak in volcanic hot springs, and enjoy a Greek BBQ with unlimited beer, wine, and soft drinks. Hotel pickup and drop-off are included.

“Great trip! Food was fantastic and service was amazing! Would highly recommend doing this excursion!”

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4.Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 268 reviews · 5 hours (approx.) · from $229

Spend about five hours aboard a small catamaran from Vlychada Marina, with hotel pickup, Red and White Beach views, caldera sailing, swimming near the volcanic islands, and a seafood BBQ with unlimited drinks. Day and sunset departures are available. Crew members have included Maria, Joe, Dimitris, Nancy, Panos, and George.

“Amazing tour, staff really sweet, food delicious and a lot of plates we didnt eat everything. Views are incredible, really worth it. We had an amazing time i would do it again !”

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5.Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

★★★★★★★★★★4.5 · 208 reviews · 6 hours (approx.) · from $96

Spend about six hours sailing Santorini’s caldera with a shared group of up to 130 people. Hike the volcano, swim to Palea Kameni’s warm springs, eat a Greek buffet with wine, and watch sunset near Oia. Guides including Tito, Toto, and Cesar have led departures, while pickup is available for an added cost.

“This tour was great. Everything from the pickup to the stops was excellent. The guide was really amazing too. You should totally do it.”

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6.Santorini Caldera: Sunset Sailing Cruise with Meal

★★★★★★★★★★4.8 · 68 reviews · 5 hours · from $147

Join a small sailing group of up to 10 for a five-hour Santorini cruise from Vlychada Marina. You’ll pass Red Beach, White Beach and Aspronisi, swim near Mesa Pigadia and Palea Kameni, see the caldera villages from the water, and eat a crew-prepared seafood barbecue with Greek wine and beer. Hotel pickup is included.

“Chris & Mariangela made this Experience perfect for us! I can recommend it 100 %”

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7.Dream Catcher 5-hour Sailing Trip in the Caldera

★★★★★★★★★★4.7 · 61 reviews · 5 hours · from $147

Spend five hours sailing from Vlihada Marina past Akrotiri, Red and White Beaches, the Indian Head Mountain, and the Caldera. Swim at secluded bays, visit the hot springs, snorkel, and enjoy a barbecue with beer, wine, and sodas. English-speaking guides, hotel pickup, and drop-off are included.

“By far one of my favorite parts of the trip because you get food, views, a great sail, and to swim”

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8.Santorini Caldera: Morning Sailing Cruise with Meal

★★★★★★★★★★4.7 · 31 reviews · 5 hours · from $147

Spend five hours sailing from Vlychada Marina through Santorini’s caldera, with photo stops at Red Beach, White Beach, and the Indian rock. Swim at Mesa Pigadia, explore the volcanic waters near Palea Kameni, and enjoy a seafood BBQ with Greek wine. Hotel transfers and snorkeling gear are included for groups of up to 10.

“Giornata meravigliosa super rilassante Buono il cibo equipaggio cordiale e compagnia anche ottima”

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9.Private 5-Hour Sunset Sailing Tour with Dinner

★★★★★★★★★★4.9 · 8 reviews · 5 hours · from $1,178 whole boat, up to 4

You’ll sail from Vlychada with a private crew, stopping near Santorini’s red and white beaches, lighthouse, hot springs, and Thirassia. Swim, snorkel, eat a Greek dinner, and watch the sunset over the caldera. Jorge and Antonio are among the crew members named in past sailings, and you may steer if sea conditions allow.

“Un équipage à notre écoute qui a su nous proposer un itinéraire différent pour profiter des lieux loin de la foule et des centaines de bateaux sur la caldeira. Un capitaine adorable qui a permis aux enfants de barrer le bateau pendant un long moment et surtout le plaisir de naviguer au retour sans moteur et uniquement à la voile! Nous étions les derniers sur l eau. Partis les premiers pour être avant tout le monde et rentres les derniers pour voir le sunset et profiter du calme. En prime un repas excellent! Sans hésitation nous referons appel à Georges pour une autre croisière. C est un vrai pro et…”

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