Cyclades Islands Sailing Trips

Cyclades Islands Sailing Trips

Cruises, Sailing & Water Tours See all

Only Show: Day Cruises | Lunch Cruises | Multi-day Cruises | Sailing Trips | Sunset Cruises

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Santorini Caldera Cruise Including Buffet and Drinks

5 star rating: Highly Recommended 72 Reviews

Cruise around the postcard-perfect island of Santorini on this 5-hour, luxury catamaran tour. Choose from a daytime or sunset cruise, then take in ...  Read more

Location: Santorini, Greece
Duration: 5 hours

From USD $171.47

Santorini Sailing Semi Private Tour

5 star rating: Highly Recommended 26 Reviews

Experience with a small group, the beauty of Santorini and the magic of sailing in the Caldera with the most magnificent views. Swim and snorkel in a ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $188.61

Ocean Voyager 74 Sailing in Santorini Sunset Tour

5 star rating: Highly Recommended 39 Reviews

Enjoy a perfect sailing Sunset tour in the magnificent island of Santorini on board the Ocean Voyager 74 catamaran. Catamaran sails to the most ...  Read more

Location: Oia, Greece
Duration: 5 hours

From USD $108.60

Santorini Sailing Dream Catcher

5 star rating: Highly Recommended 4 Reviews

Santorini's notorious Dream Catcher tour lets you experience with a small group, the beauty of Santorini and the magic of sailing in the Caldera with the most ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $120.03

Santorini Lagoon 560 Sunset tour

5 star rating: Highly Recommended 9 Reviews

Perfect Luxury Sailing experience in the magnificent island of Santorini with amazing lagoon 560 catamaran. Sailing in luxury and style on the biggest ...  Read more

Location: Oia, Greece
Duration: 5 hours

From USD $165.75

Mykonos Catamaran Sailing Tours

5 star rating: Highly Recommended 8 Reviews

Mykonos Catamaran sailing tours: the top thing to do in Mykonos!  Sail on a stable and safe catamaran for a unique sailing experience. Alternative, ...  Read more

Location: Míkonos, Greece
Duration: 6 hours

From USD $115.45

Ocean Voyager 74 Sailing in Santorini Day

5 star rating: Highly Recommended 25 Reviews

Enjoy a perfect sailing Day tour in the magnificent island of Santorini on board the Ocean Voyager 74 catamaran. Catamaran sails to the most amazing sights of ...  Read more

Location: Santorini, Greece
Duration: 5 hours

From USD $108.60

Small-Group Full-Day Sailing Yacht Cruise to Delos and Rhenia Islands

4.5 star rating: Recommended 14 Reviews

Visit the natural insular archaeological site of Delos and enjoy swimming to a secluded cove off the uninhabited island of Rhenia on an 8-hour yacht ...  Read more

Location: Míkonos, Greece
Duration: 8 hours

From USD $108.60

Sailing Catamaran Cruise in Santorini

5 star rating: Highly Recommended 3 Reviews

This is not just an ordinary day cruise. Choose either morning or afternoon departure and enjoy some amazing scenery. This 5-hour cruise will leave you with ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $114.31

Beautiful Day and Romantic Sunset Tour from Oia

5 star rating: Highly Recommended 5 Reviews

Sail in this luxurious catamaran which is recommended for semi private tours and that can comfortably accommodate 18 passengers. The tour departs ...  Read more

Location: Oia, Greece
Duration: 5 hours

From USD $171.47

Viator Exclusive: Luxury Catamaran Santorini Day Tour

5 star rating: Highly Recommended 2 Reviews

Prepare to explore the beauty of Santorini's volcanic landscape by sea on this 5 hour sailing trip on board the newest addition to our fleet, the brand new ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $165.75

Half-Day Sailing Trip from Santorini

5 star rating: Highly Recommended 14 Reviews

If you seek to explore the beauties of Santorini Island on a luxurious catamaran but not spend much, then the Tahiti 80 'Ios' is the perfect match for you. The ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $108.60

Private Tour: Santorini Caldera Cruise Including Buffet and Drinks

5 star rating: Highly Recommended 4 Reviews

Cruise around Santorini in style on this private, 5-hour cruise by luxury catamaran. Choose from a daytime or sunset cruise, then laze on deck and soak up ...  Read more

Location: Santorini, Greece
Duration: 5 hours

From USD $207.19

Semi-private Day or Sunset Tour

4.5 star rating: Recommended 7 Reviews

This luxurious sailing yacht is recommended mostly for semi private tours that can comfortably accommodate 45 passengers. The tours ...  Read more

Location: Oia, Greece
Duration: Flexible

From USD $108.60

Caldera Catamaran Gold ''Sunset Cruise''

5 star rating: Highly Recommended 2 Reviews

A semi-private luxury cruise is one of the best ways to view a romantic sunset and feel the energy of the island accompanied by a glass of wine. A great choice ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $171.47

Viator Exclusive: Santorini Luxury Catamaran Sunset Tour

4.5 star rating: Recommended 4 Reviews

Enjoy the magnificent sunset of Santorini on this 5-hour sailing trip aboard the newest addition to the fleet, the brand new Lagoon 520. With its beautiful ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $165.75

Milos Sailing Experience

5 star rating: Highly Recommended 2 Reviews

If you love the sea, if you seek to escape from the everyday routine, if you long for the intense emotions in nature, if you seek to broaden your ...  Read more

Location: Milos, Greece
Duration: 11 hours

From USD $114.31

Caldera Traditional Boat ''Day Cruise''

5 star rating: Highly Recommended 3 Reviews

The Traditional Way of Luxury Cruises!... Get on board to Kaiki ( A caïque-kaiki, is the term for a traditional fishing boat usually found among the ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $97.16

Semi-Private Cruise - Day or Sunset Tour

5 star rating: Highly Recommended 1 Review

Lagoon 450 is an amazing sailing catamaran, that can comfortably accommodate 16 passengers. You will have the opportunity to visit the best ...  Read more

Location: Oia, Greece
Duration: Flexible

From USD $160.04

Lagoon 500 Santorini Day tour

5 star rating: Highly Recommended 2 Reviews

A perfect sailing experience awaits you with the Lagoon 500 'Sunset Oia' catamaran. With a small group of people Lagoon 500 performs an all inclusive sailing ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $165.75

Small-Group Full-Day Sailing Yacht Cruise to Rhenia Island

4.5 star rating: Recommended 4 Reviews

Escape the crowded beaches of Mykonos on a 7-hour yacht cruise to the uninhabited island of Rhenia, also known as the “Big Delos”. Enjoy the privacy of a fine ...  Read more

Location: Míkonos, Greece
Duration: 7 hours

From USD $85.73

Tahiti 80 Sailing in Santorini Sunset Trip

5 star rating: Highly Recommended 1 Review

Let yourself be amazed by the magnificent sunset and beautiful sights of Santorini on-board of the Tahiti 80. Relax on the spacious deck and enjoy the foods ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $108.60

Morning Caldera Sailing Cruise

5 star rating: Highly Recommended 2 Reviews

Step aboard this 5 hour morning cruise for a relaxed sail and enjoy your time swimming, sunbathing, snorkeling, taking photos, tasting delicious BBQ meals, ...  Read more

Location: Vlichada, Greece
Duration: 5 hours

From USD $120.03

Go Fishing in Santorini

5 star rating: Highly Recommended 1 Review

Captain George gives you the chance to go fishing in Santorini, sail around the Caldera and taste the local goodies.

Location: Fira, Greece
Duration: 5 hours

From USD $114.31

Lagoon 560 Santorini Day Tour

Sail along with the most luxurious Lagoon catamaran in Santorini. Lagoon 560 performs an all inclusive Day tour to the most interesting sights in Santorini. ...  Read more

Location: Thera, Greece
Duration: 5 hours

From USD $165.75
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Only Show: Day Cruises | Lunch Cruises | Multi-day Cruises | Sailing Trips | Sunset Cruises

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