Top Cyclades Islands Sailing Trips

153 Results
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 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
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
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
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
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 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 Free Cancellation
4.9 (9)
from
$236
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
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
Semi-private Day Cruise

Experience a premium boat trip with up to 25 guests aboard our spacious 66ft traditional wooden boat, complete with sunbeds and plenty of room to …More

Likely to Sell Out
Likely to Sell Out
Antiparos, Greece

Experience a premium boat trip with up to 25 guests aboard our spacious 66ft traditional wooden boat, complete with sunbeds and plenty of room to...

6 hours 45 minutes Free Cancellation
4.9 (159)
from
$218
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
Milos Full-Day Premium Catamaran Cruise Kleftiko and Polyegos

Experience the magic of Milos on a luxury catamaran cruise designed for total comfort and adventure. Your journey begins at Adamantas, sailing first to the …More

Milos, Greece

Experience the magic of Milos on a luxury catamaran cruise designed for total comfort and adventure. Your journey begins at Adamantas, sailing first to the...

9 hours Free Cancellation
5.0 (20)
from
$218
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
Premium Santorini Private Day Tour Elba 45, BBQ, drinks, transfer

Explore the most attractive sights and beaches in Santorini on board the Luxurious Lagoon 450, exclusively for your party. Captain and crew will make this …More

Santorini, Greece

Explore the most attractive sights and beaches in Santorini on board the Luxurious Lagoon 450, exclusively for your party. Captain and crew will make this...

5 hours Hotel pickup offered Free Cancellation
4.9 (45)
from
$210
Santorini Oia: Private Sunset Cruise with Fresh Fish BBQ & Drinks

The Sunset Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay is a great opportunity to enjoy a sailing cruise at the …More

Santorini, Greece

The Sunset Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay is a great opportunity to enjoy a sailing cruise at the...

6 hours Hotel pickup offered Free Cancellation
5.0 (46)
from
$209
Catamaran Half Day Shared Kleftiko Trip

Choose Morning 9:00-14:00 or Afternoon 14:30-19:30 Boarding time is 30' minutes before departure. Be on time. Itinerary of the cruise Welcome on board! We sail …More

Milos, Greece

Choose Morning 9:00-14:00 or Afternoon 14:30-19:30 Boarding time is 30' minutes before departure. Be on time. Itinerary of the cruise Welcome on board! We sail...

5 hours Free Cancellation
5.0 (243)
from
$204
South Paros Antiparos Despotiko Faragas Beach Sailboat SY AGERAS

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

Paros, Greece

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

8 hours Free Cancellation
4.9 (9)
from
$195

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