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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.

“Such a great and beautiful experience on a girl’s trip. The Caldera crew were so amazing and accommodating. The food was great, thanks to the chef and overall it was everything and beyond what we expected. Thank you!”

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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

2.Santorini: Luxury Catamaran Day Trip with Meal and Open Bar

4.8

Luxury Santorini catamaran with hotel pickup, open bar, Greek lunch, snorkel stops, volcanic hot springs, and sunset views near Oia.

“We had a fabulous day on our catamaran! The boat was stunning and the staff were great. The food was absolutely gorgeous and all drinks were included - beer, wine and soft drinks and a cocktail whilst watching the sunset. The taxi picked us up perfectly on time and on the boat we did three…”

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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

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.

“The perfect day! Our guided were all so kind and accommodating. The boat was beautiful, spacious, and had plenty of fun equipment. The lunch was delicious and abundant, as well and the drinks! Overall, a fantastic experience. Would absolutely do it again!”

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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

6.Santorini: Catamaran Caldera Cruise with Meal and Drinks

4.7

A 5-hour Santorini caldera catamaran cruise from Ammoudi with hotel transfer, snorkeling stops, BBQ, and open bar included.

“This was a fantastic way to spend the afternoon cruising the caldera! Everything was perfect! Driver picked us up at the meeting point 1 minute walk from our hotel. Crew was polite, professional and fun! Dinner they served was delicious & plentiful. Stops were beautiful along the way. Dance party as the sun was setting…”

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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

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

5.0

Santorini catamaran cruise with Greek meal, open bar, hot springs, Red Beach swims, and sunset views from the water.

“The whole thing was extremely well coordinated from pick up to drop off. This cruise was one of the biggest highlights of our time in Greece. The crew was amazing and our group was really fun. The swimming was so fun The meal was delicious and the final sunset was simply magical. Thank you for…”

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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.

“This was the best day out! Couldn’t recommend it enough. You get to see all of the best spots in Milos, stop for swims in the most beautiful water and get provided with plenty of food and drinks throughout the day. Dora was our guide and she made sure we all had an incredible day.”

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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

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 entire experience was incredible. Beautiful day crew was awesome the scenery spectacular the sunset in Oia breathtaking. The BBQ lunch and beverage provided delicious. Couldn’t have asked for a better time.”

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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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