Cyclades Islands Sailing Trips

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

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Vlychada Marina. Sail past the island's highlights, such as the Red & White …More

Santorini, Greece

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Vlychada Marina. Sail past the island's highlights, such as the Red & White...

5 hours Free Cancellation
5.0 (7,648)
from
$148
Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Vlychada Marina. Sail past the island's highlights, such as the Red & White …More

Santorini, Greece

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Vlychada Marina. Sail past the island's highlights, such as the Red & White...

5 hours Free Cancellation
4.9 (3,723)
from
$91
Milos Small-Group Full-Day Cruise with Snorkelling and Lunch

The cruise is done at a relaxed pace, trying to avoid crowds with only 12 passengers aboard the sailing boat. Boats are equipped with large …More

Milos, Greece

The cruise is done at a relaxed pace, trying to avoid crowds with only 12 passengers aboard the sailing boat. Boats are equipped with large...

8 hours Free Cancellation
5.0 (1,552)
from
$183
Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

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

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

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

5 hours Hotel pickup offered Free Cancellation
4.9 (1,222)
from
$125
Mykonos: Brand-New Catamaran Cruise with Meal, Drinks & Transport

Cruise with Nostos Mykonos Yachts in sophisticated chic style and discover the gorgeous waters of the nearby Rhenia island or the famous Mykonian southern coast …More

Mykonos, Greece

Cruise with Nostos Mykonos Yachts in sophisticated chic style and discover the gorgeous waters of the nearby Rhenia island or the famous Mykonian southern coast...

5 hours Hotel pickup offered Free Cancellation
4.9 (1,190)
from
$136
Catamaran Day & Sunset Cruises with meals Drinks and transportation

• Cruise Duration: 5.00 Hours • Choice of a Morning or Sunset Cruise • Swim and snorkeling stop (Snorkeling Equipment Included) • Snap photos of …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

• Cruise Duration: 5.00 Hours • Choice of a Morning or Sunset Cruise • Swim and snorkeling stop (Snorkeling Equipment Included) • Snap photos of...

5 hours Hotel pickup offered Free Cancellation
4.9 (1,150)
from
$126
Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Ammoudi Bay or Vlychada Marina. Sail past the island's highlights, such as the Red …More

Santorini, Greece

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Ammoudi Bay or Vlychada Marina. Sail past the island's highlights, such as the Red...

5 hours Free Cancellation
4.9 (953)
from
$184
Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

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 …More

Santorini, Greece

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...

5 hours Hotel pickup offered Free Cancellation
4.9 (710)
from
$138
Mykonos Sail Cruise to Delos and Rhenia Islands

Hop on board and live a unique cruise experience in Mykonos island. Sail to the ancient Delos, explore this UNESCO World Heritage site, swim in …More

Mykonos, Greece

Hop on board and live a unique cruise experience in Mykonos island. Sail to the ancient Delos, explore this UNESCO World Heritage site, swim in...

6 hours Free Cancellation
4.9 (666)
from
$144
Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer

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 …More

Santorini, Greece

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...

5 hours Hotel pickup offered Free Cancellation
4.8 (585)
from
$90
Santorini Private Catamaran Cruise with BBQ, Open Bar & Transfers

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Vlychada Marina. Sail past the island's highlights, such as the Red & White …More

Santorini, Greece

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Vlychada Marina. Sail past the island's highlights, such as the Red & White...

5 hours Hotel pickup offered Free Cancellation
5.0 (452)
from
$146
Luxury Santorini Catamaran Cruise: Lunch, BBQ, Drinks, Transfers

Our Santorini day cruise starts from the picturesque port of Vlychada, sailing onwards to explore the beauty of the Red Beach, White Beach, Indian Rocks, …More

Santorini, Greece

Our Santorini day cruise starts from the picturesque port of Vlychada, sailing onwards to explore the beauty of the Red Beach, White Beach, Indian Rocks,...

5 hours Hotel pickup offered Free Cancellation
5.0 (447)
from
$103
Milos oneiro-kleftiko sailing experience with local guide

Tour with a sailing boat like a semi private trip with a small group of people. Our local skipper offers a slow close-up approach of …More

Milos, Greece

Tour with a sailing boat like a semi private trip with a small group of people. Our local skipper offers a slow close-up approach of...

7 hours Free Cancellation
5.0 (441)
from
$161
The Authentic Rhenia-Delos Cruise

Sparkling seas and secluded beaches? Join our Rhenia – Delos cruise and live a day like no other! The Cycladic Sisters, Mykonos, Delos and Rhenia, …More

Mykonos, Greece

Sparkling seas and secluded beaches? Join our Rhenia – Delos cruise and live a day like no other! The Cycladic Sisters, Mykonos, Delos and Rhenia,...

6 hours 30 minutes Free Cancellation
4.8 (432)
from
$102
Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

Explore Santorini's volcanic landscape by sea on this 5-hour sailing trip aboard a new luxury catamaran. With its sleek, diamond-like design and comfortable seating areas …More

Santorini, Greece

Explore Santorini's volcanic landscape by sea on this 5-hour sailing trip aboard a new luxury catamaran. With its sleek, diamond-like design and comfortable seating areas...

5 hours Hotel pickup offered Free Cancellation
4.8 (412)
from
$126
Luxury Santorini Sunset Cruise: Dinner, BBQ, Open Bar, Transfers

Get ready for an incredible Santorini Sunset Catamaran Cruise! Our adventure kicks off from the charming port of Vlychada , where we'll sail through the …More

Santorini, Greece

Get ready for an incredible Santorini Sunset Catamaran Cruise! Our adventure kicks off from the charming port of Vlychada , where we'll sail through the...

5 hours Hotel pickup offered Free Cancellation
4.9 (380)
from
$126
Milos and Polyaigos Full Day Cruise with Meals and Snorkelling

For those who wish to explore and learn everything about Milos island, this cruise will gratify you! Circumnavigate the island of Milos and visit the …More

Milos, Greece

For those who wish to explore and learn everything about Milos island, this cruise will gratify you! Circumnavigate the island of Milos and visit the...

9 to 10 hours Free Cancellation
4.9 (370)
from
$144
Santorini Fishing Private Cruise boat tour - BBQ, Snorkeling

The local captain “Makis” from “The Pirate fishing tours” in Santorini, loves to share his passion for the sea, with the visitors to Santorini island …More

Santorini, Greece

The local captain “Makis” from “The Pirate fishing tours” in Santorini, loves to share his passion for the sea, with the visitors to Santorini island...

5 hours Free Cancellation
5.0 (354)
from
$170
Santorini Catamaran Cruise: with Lunch, BBQ, Open Bar, Transfers

Step aboard our catamaran with Santorini Yachting Cruises, and join us for an incredible sailing adventure! Our day cruise sets sail from the port of …More

Santorini, Greece

Step aboard our catamaran with Santorini Yachting Cruises, and join us for an incredible sailing adventure! Our day cruise sets sail from the port of...

5 hours Hotel pickup offered Free Cancellation
5.0 (308)
from
$98
Half Day Sailing to Kleftiko with Lunch, Open Bar & Snorkeling

Kleftiko Boat Tour an unforgettable journey to Milos’ hidden gems, where adventure meets tranquility on the crystal clear waters of the Aegean. Embark on an …More

Milos, Greece

Kleftiko Boat Tour an unforgettable journey to Milos’ hidden gems, where adventure meets tranquility on the crystal clear waters of the Aegean. Embark on an...

7 hours Free Cancellation
5.0 (306)
from
$154
Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

Santorini's original and most popular sailing tour. Experience the beauty of Santorini and the magic of sailing in the Caldera on this small-group sailing tour. …More

Santorini, Greece

Santorini's original and most popular sailing tour. Experience the beauty of Santorini and the magic of sailing in the Caldera on this small-group sailing tour....

5 hours Hotel pickup offered Free Cancellation
4.9 (298)
from
$218

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