Top Cyclades Islands Sailing Trips

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Santorini Caldera Cruise Including Buffet and Drinks

5 star rating: Highly Recommended 144 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 stunning ... 

Location: Santorini, Greece
Duration: 5 hours

From USD $176.72

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

5 star rating: Highly Recommended 80 Reviews

Enjoy a perfect sailing Sunset tour in the magnificent island of Santorini on board our catamaran. The catamaran sails to the most amazing sights of Santorini ... 

Location: Oia, Greece
Duration: 5 hours

From USD $123.70

Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

5 star rating: Highly Recommended 50 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 ... 

Location: Thera, Greece
Duration: 5 hours

From USD $111.92

Mykonos Catamaran Sailing Tour

5 star rating: Highly Recommended 30 Reviews

Mykonos Catamaran sailing is the top thing to do in Mykonos!  Sail on a stable and safe catamaran for a unique sailing experience. Alternative, unforgettable ... 

Location: Míkonos, Greece
Duration: 6 hours

From USD $131.95

Sailing Catamaran Cruise in Santorini with BBQ and Drinks

5 star rating: Highly Recommended 66 Reviews

Enjoy a perfect sailing 5-hour tour from the magnificent island of Santorini onboard the catamaran, sailing to the most amazing sights of Santorini such as the ... 

Location: Santorini, Greece
Duration: 5 hours

From USD $106.03

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ and Drinks

5 star rating: Highly Recommended 68 Reviews

Perfect Luxury Sailing experience in the magnificent island of Santorini with an amazing catamaran. Sailing in luxury and style on the biggest Lagoon Catamaran ... 

Location: Oia, Greece
Duration: 5 hours

From USD $182.61

Small-Group Sailing Yacht Cruise to Rhenia and Guided Tour of Delos

4.5 star rating: Recommended 51 Reviews

Visit the natural insular archaeological site of Delos and enjoy swimming to a secluded cove off the uninhabited island of Rhenia on an 7-hour yacht cruise ... 

Location: Míkonos, Greece
Duration: 7 hours

From USD $123.70

Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

5 star rating: Highly Recommended 33 Reviews

Experience the beauty of Santorini and its volcanic caldera on this small group sailing tour. Cruise by some of the island’s best-known landmarks before ... 

Location: Thera, Greece
Duration: 5 hours

From USD $170.83

Santorini Catamaran Tour

4.5 star rating: Recommended 10 Reviews

Discover Santorini by sea on this 5-hour catamaran tour. Admire the island’s volcanic sights, visit its impressive beaches, and soak in its thermal hot ... 

Location: Oia, Greece
Duration: 5 hours

From USD $117.81

Private Tour: Santorini Caldera Cruise Including Buffet and Drinks

5 star rating: Highly Recommended 6 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 the ... 

Location: Santorini, Greece
Duration: 5 hours

From USD $195.57

Santorini Volcanic Islands Cruise: Volcano, Hot Springs and Thirassia

Walk to reach the crators of the active volcano. Swim at volcano's Hot Springs. Enjoy free time in Thirassia. Admire amazing views of Santorini from a ... 

Location: Órmos Athiniós, Greece
Duration: 6 hours

From USD $41.23

Elegant Sailing Yacht Cruise to Mykonos South Beaches, Delos & Rhenia Islands

Set the sails to the wind and explore the exclusive beauties of Mykonos on a spacious and elegant 112-foot Super-Sailing Yacht with rich on-board buffet and ... 

Location: Mykonos, Greece
Duration: 6 hours

From USD $111.92

Milos Sailing Tour with Snorkeling

5 star rating: Highly Recommended 8 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 horizons, ... 

Location: Milos, Greece
Duration: 11 hours

From USD $164.94

Private Motor Yacht Cruise in Santorini with BBQ and Drinks

5 star rating: Highly Recommended 3 Reviews

"Oceanis” is a unique motor yacht that can offer a lifetime experience around Santorini and the Aegean Islands. It has the ability to take you literally ... 

Location: Thera, Greece
Duration: Flexible

From USD $1,767.19

Santorini Small-Group Catamaran Sailing Trip with BBQ and Drinks

5 star rating: Highly Recommended 1 Review

Choose from a morning or afternoon departure and after your hotel pickup, embark on a 5-hour, small-group sailing trip to the most magnificent sights of ... 

Location: Thera, Greece
Duration: 5 hours

From USD $194.39

Sunset Caldera Sailing Cruise

5 star rating: Highly Recommended 2 Reviews

Captain Yiannis and his crew -all experienced sailors- can assure you that all claims about greek hospitality are true and that this cruise will be the most ... 

Location: Vlichada, Greece
Duration: 5 hours

From USD $147.27

Private Catamaran Day Tour in Santorini Including Lunch and Drinks

5 star rating: Highly Recommended 1 Review

Prepare to embark on a journey of exploration. Visit the most magnificent landmarks of Santorini by sea on our luxurious Emily power catamaran. We recommend ... 

Location: Thera, Greece
Duration: 5 hours

From USD $1,178.13

Milos Sailing Tour with Lunch

5 star rating: Highly Recommended 1 Review

Explore the most beautiful island  in Cyclades leave the dream. The west part of the island the most picturesque part!

Location: Milos, Greece
Duration: Flexible

From USD $141.38

Mykonos Adult Only Sunset Sailing Aperitivo Cruise

The debut in Mykonos of the true Adult-only cruise for an on board-“Aperitivo” and soft music while the sun drowns in the Aegean Sea. Peace, Relaxation and ... 

Location: Mykonos, Greece
Duration: 2 hours 30 minutes

From USD $64.80

Morning Caldera Sailing Cruise

5 star rating: Highly Recommended 3 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, ... 

Location: Vlichada, Greece
Duration: 5 hours

From USD $147.27

Milos Half Day Cruise with Lunch

Enjoy a half -day cruise and discover the most beautiful places in Milos!

Location: Milos, Greece
Duration: 5 hours

From USD $94.25

Milos and Poliegos Island Cruise with Lunch

Explore the majestic Milos island!

Location: Milos, Greece
Duration: 11 hours

From USD $164.94

Trimaran Sailing in Caldera

If you are young at the heart and love adventure, join our crew for 6 hours real sailing experience inside the magnificent Caldera of Santorini on impressive ... 

Location: Vlichada, Greece
Duration: 6 hours

From USD $206.17

Ios Sunset Sailing trip

Spend your afternoon at Ios, aboard a Pirate ship! Join our half-day atmospheric trip starting daily from Ios port, on the right time before you hit the bars. ... 

Location: Ios, Greece
Duration: 3 hours

From USD $41.23

Private Motor Yacht Cruise with Drinks

Explore Caldera of Santorini, multi-colored Volcanic beaches, Hot Springs or nearby Aegean islands.Get on board for luxury private cruise.

Location: Vlichada, Greece
Duration: 5 hours

From USD $1,390.19
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