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15 Best Sailing In Greece

The Greek classics.

The 15 most popular sailing in Greece, with what each one is really like on the day, who runs it, and what it costs.

15 Best Sailing In Greece

Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer

Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer - The Red Beach and White Beach photo run (and why it’s actually smart)

1.Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer

Most Popular 5.0

Small-group catamaran cruise in Santorini with BBQ, open bar, and multiple swim stops including the hot springs near Akrotiri and Thirasia.

“Amazing experience!! Beautiful sunset, great food, and fun swimming. Capitan and crew were so much fun and made sure everyone was having a blast throughout the evening! Must do!!!”

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Santorini: Luxury Catamaran Day Trip with Meal and Open Bar

Santorini: Luxury Catamaran Day Trip with Meal and Open Bar - Snorkel and Swim Stops: What You’ll Do in the Water

Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar

Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar - Santorini volcano and hot springs: your warm-water reality check

3.Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar

5.0

Small-group Santorini catamaran cruise from Vlychada with hotel pickup, Prosecco and open bar, Red Beach and hot springs swims, plus BBQ lunch.

“Relaxing cruise. The staff was friendly and knowledgeable. Excellent customer service and tge food was great. Definitely recommend.”

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Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar

Santorini Gold Catamaran Cruise with Snorkel, BBQ & Open Bar - White Beach views and the Venetian lighthouse from sea level

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Where you meet in Heraklion, and how timing works

5.Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

4.8

Small-group sailing from Heraklion to Dia Island with swim, snorkel, SUP, and a Mediterranean meal plus unlimited drinks in 5.5 hours.

“Here’s a smoother, more natural version of your text: This was the last day of our trip through Crete, and we ended it in the best way possible. The cruise was incredible, the weather was perfect, and the crew and food were fantastic. It was everything I wanted and more. We were having so much…”

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Santorini: Catamaran Caldera Cruise with Meal and Drinks

Santorini: Catamaran Caldera Cruise with Meal and Drinks - Pickup that actually works: from your hotel to the dock

Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks

Rhodes: All-Inclusive Catamaran Cruise with Lunch and Drinks - Sailing vs Power catamaran: choosing the right route for your day

Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset

Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset - Price and value: what $181.39 buys you on the water

Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch - Sarakiniko and Glaronisia: The Volcanic Milos “Book Cover” Moments

9.Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

4.9

A full-day Milos sail from Adamas with boat-only swimming, Kleftiko cave snorkeling, lunch in a wild setting, and Polyaigos water.

“Boat was great, weather was amazing, views were unforgettable. Dora & her team made our experience so much more enjoyable, she was fantastic. We had a great day. Michael & Susan 🇦🇺”

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Santorini: Sailing Catamaran Cruise with BBQ and Drinks

Santorini: Sailing Catamaran Cruise with BBQ and Drinks - The morning vs sunset cruise: what changes and why you should care

10.Santorini: Sailing Catamaran Cruise with BBQ and Drinks

4.7

Sail past Santorini’s Red and White Beaches, snorkel hot springs and the caldera, then enjoy BBQ and drinks on a luxury catamaran.

“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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Santorini: Catamaran Tour with BBQ Meal and Unlimited Drinks

Santorini: Catamaran Tour with BBQ Meal and Unlimited Drinks - Pickup and Getting to Ammoudi or Vlychada Without Stress

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island time: swimming and snorkeling that you’ll remember

12.Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

4.8

Sail from Heraklion to Dia Island with snorkeling, SUP, lunch, and unlimited drinks on a luxury yacht. Shared or private options.

“A memory for a lifetime. the staff were super professional and accommodating. the sailing was smooth and beautiful and the sea was Cristal clear and just the right temperature.”

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Luxury Catamaran Cruise from Athens with Traditional Greek Meal and BBQ

Luxury Catamaran Cruise from Athens with Traditional Greek Meal and BBQ - Your Sea Route: Coast Views and Real Time to Relax

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer - Red Beach and White Beach: the real “vacation” part of the day

14.Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

5.0

Sail Santorini’s caldera on a luxury catamaran with hotel transfers, Red and White Beach swims, BBQ, drinks, snorkeling, and a sunset view.

“The Santorini Sunset Luxury Sailing Catamaran Cruise was absolutely amazing! From start to finish, everything was so well organized — the transfer was smooth, the crew was friendly and fun, and the atmosphere onboard was incredible. The BBQ meal was delicious (honestly one of the best we had in Santorini!), and the unlimited drinks kept…”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Getting Picked Up: The Santorini Logistics Win

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