Top Cyclades Islands Sailing Trips

153 Results
Sailsational Luxury Santorini Catamaran Sunset Cruise with Dinner

The limited number of participants makes this catamaran sailing experience unique and different. At most, 12-20 guests take place on this catamaran sailing tour. It …More

Santorini, Greece

The limited number of participants makes this catamaran sailing experience unique and different. At most, 12-20 guests take place on this catamaran sailing tour. It...

5 to 6 hours Hotel pickup offered Free Cancellation
4.8 (19)
from
$218
One Full Day of True Sailing to South Naxos & Koufonisi SY AGERAS

We sail from Piso Livadi towards South Naxos by 09:00, hoisting our sails & adjusting our course according to the prevailing winds we enjoy a …More

Paros, Greece

We sail from Piso Livadi towards South Naxos by 09:00, hoisting our sails & adjusting our course according to the prevailing winds we enjoy a...

10 hours Free Cancellation
5.0 (8)
from
$222
5 Hour Private Day or Sunset Cruise in Large & Majestic Catamaran

Step aboard this large and majestic catamaran (equipped with all the amenities of a 5 star floating hotel including AC) and enjoy a comfortable and …More

Mykonos, Greece

Step aboard this large and majestic catamaran (equipped with all the amenities of a 5 star floating hotel including AC) and enjoy a comfortable and...

5 hours Free Cancellation
5.0 (6)
from
$223
Full Day Tour to Kleftiko, Firlingos and Poliegos Catamaran

Sailing across the coastline, we will pass by the traditional fishing villages of Skinopi, Klima with the colorful little houses – called “Sirmata”- built by …More

Milos, Greece

Sailing across the coastline, we will pass by the traditional fishing villages of Skinopi, Klima with the colorful little houses – called “Sirmata”- built by...

10 hours Free Cancellation
5.0 (7)
from
$223
Santorini Private Tour Half-Day Sailing Platinum Catamaran Cruise

This tour provides a complete experience of Santorini! You can swim in unique and otherwise impassable locations, enjoying the most wonderful of vistas while sailing …More

Santorini, Greece

This tour provides a complete experience of Santorini! You can swim in unique and otherwise impassable locations, enjoying the most wonderful of vistas while sailing...

5 hours Hotel pickup offered Free Cancellation
4.9 (9)
from
$236
Catamaran Full Day Cruise: Poliegos - Kleftiko

If you love the sea, if you seek to escape from the everyday routine, if you long for the intense emotions of nature, if you seek …More

Milos, Greece

If you love the sea, if you seek to escape from the everyday routine, if you long for the intense emotions of nature, if you seek...

9 hours 30 minutes Free Cancellation
4.9 (90)
from
$241
Milos & Poliegos Catamaran Cruise Homemade Full menu BBQ & Drinks

Experience a luxury full-day cruise aboard the new catamaran Lagoon 46 “Naya II”, where elegance meets comfort and have a special day by exploring the …More

Milos, Greece

Experience a luxury full-day cruise aboard the new catamaran Lagoon 46 “Naya II”, where elegance meets comfort and have a special day by exploring the...

9 to 10 hours Free Cancellation
5.0 (53)
from
$241
Santorini Full Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport

Enjoy unique views of Santorini from the sea during this 7 hour daycruise, starting from the port of Vlychada. Passing from the Red Beach you …More

Santorini, Greece

Enjoy unique views of Santorini from the sea during this 7 hour daycruise, starting from the port of Vlychada. Passing from the Red Beach you...

7 hours Hotel pickup offered Free Cancellation
4.9 (16)
from
$261
Santorini Private Sunset Sailing Tour with Dinner, Drinks &Transfer included

The company Angel Sailing was founded by the merchant marine’s captain George, who after being on duty in oceangoing ships for the last 15 years, …More

Santorini, Greece

The company Angel Sailing was founded by the merchant marine’s captain George, who after being on duty in oceangoing ships for the last 15 years,...

5 hours Hotel pickup offered Free Cancellation
5.0 (183)
from
$269
Santorini Private Daytime Sailing Cruise with Meal, Drinks &Transfer included

The company Angel Sailing was founded by the merchant marine’s captain George, who after being on duty in oceangoing ships for the last 15 years, …More

Santorini, Greece

The company Angel Sailing was founded by the merchant marine’s captain George, who after being on duty in oceangoing ships for the last 15 years,...

5 hours Hotel pickup offered Free Cancellation
5.0 (91)
from
$269
Private Full One-Day Tour Naxos & Heraklia SY AGERAS

Words, pictures or videos are not enough to describe the experience onboard the Yin Yang. From the moment you will first see the yacht until …More

Paros, Greece

Words, pictures or videos are not enough to describe the experience onboard the Yin Yang. From the moment you will first see the yacht until...

8 hours Free Cancellation
5.0 (29)
from
$365
Private Full Day Tour in South Paros Caves Despotiko

We sail from Pisso Livadi to the southwest by 09:30, hoisting our sails and adjusting our course according to the prevailing winds we enjoy a …More

Paros, Greece

We sail from Pisso Livadi to the southwest by 09:30, hoisting our sails and adjusting our course according to the prevailing winds we enjoy a...

8 hours Free Cancellation
5.0 (32)
from
$367
Santorini Full-Day Private Experience: Sailing & Island Excursion

Enhance your visit to the world's most unique island with a full-day private tour of Santorini, and enjoy the opportunity to observe the island's beauty …More

Santorini, Greece

Enhance your visit to the world's most unique island with a full-day private tour of Santorini, and enjoy the opportunity to observe the island's beauty...

9 hours Hotel pickup offered Free Cancellation
from
$402
Private 2 Hours Sunset Cruise in Milos — Magical Klima Village

Heading to Klima promises not just a glimpse but a full immersion in nature's canvas at sunset. The way hues blend and dance across the …More

Milos, Greece

Heading to Klima promises not just a glimpse but a full immersion in nature's canvas at sunset. The way hues blend and dance across the...

2 hours Free Cancellation
5.0 (3)
from
$531
Explore Santorini and its volcanic wonders with Alex Private Boat

Join us on this breathtaking trip to Nea and Palea Kammeni,the lava islands in the middle of the crater. First up, we will see the …More

Santorini, Greece

Join us on this breathtaking trip to Nea and Palea Kammeni,the lava islands in the middle of the crater. First up, we will see the...

3 hours Free Cancellation
5.0 (48)
from
$574
Half-Day Private Romantic Sailing Getaway to Kleftiko

The best custom sailing experience in Milos for the best price! Come on board Veronica classic yacht and sail the south coast of the island …More

Milos, Greece

The best custom sailing experience in Milos for the best price! Come on board Veronica classic yacht and sail the south coast of the island...

5 hours Free Cancellation
5.0 (78)
from
$689
Private Mykonos Cruise: Rhenia Swim & Little Venice Sunset

Have you ever seen a sunset at Aegean ? Mykonos is not only known for wild nightlife and dancing, is also a very romantic destination, …More

Mykonos, Greece

Have you ever seen a sunset at Aegean ? Mykonos is not only known for wild nightlife and dancing, is also a very romantic destination,...

4 to 5 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$746
Private luxury Sunset Cruise to the Blue Lagoon

Sail to the famous Blue Lagoon at sunset and experience the magic of turquoise waters surrounded by the islets of Panteronisi, Tigani, and Glaropounda. Perfect …More

Paros, Greece

Sail to the famous Blue Lagoon at sunset and experience the magic of turquoise waters surrounded by the islets of Panteronisi, Tigani, and Glaropounda. Perfect...

2 hours Free Cancellation
from
$789
Santorini Caldera Private Sailing Boat Cruise

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private …More

Santorini, Greece

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private...

5 hours Hotel pickup offered Free Cancellation
4.9 (53)
from
$976
Private Yacht Tour in Santorini (Technohull) - Open Bar&Transfers

• Sail along the iconic caldera, passing volcanic cliffs, the famous Red Beach, and the White Beach. • Swim in crystal-clear waters, explore hidden coves, …More

Santorini, Greece

• Sail along the iconic caldera, passing volcanic cliffs, the famous Red Beach, and the White Beach. • Swim in crystal-clear waters, explore hidden coves,...

5 hours Hotel pickup offered Free Cancellation
from
$1,027

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