Cyclades Islands Sailing Trips

153 Results
Santorini Half Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport

Enjoy unique views of Santorini from the sea during this 5 hour morning or sunset cruise. Starting from the port of Vlychada, see the Vlychada …More

Santorini, Greece

Enjoy unique views of Santorini from the sea during this 5 hour morning or sunset cruise. Starting from the port of Vlychada, see the Vlychada...

5 hours Hotel pickup offered Free Cancellation
4.9 (87)
from
$160
Kleftiko Full Day Sailing Cruise with Snorkeling & Lunch

Discover the beautiful coast line of Milos and its fantastic and unapproachable beaches with our sailing yachts and find an exciting and alternative way in …More

Milos, Greece

Discover the beautiful coast line of Milos and its fantastic and unapproachable beaches with our sailing yachts and find an exciting and alternative way in...

9 to 10 hours Free Cancellation
4.9 (133)
from
$160
Santorini Sailing for Cruise Guests A Volcano and Beach Tour

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a …More

Santorini, Greece

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a...

6 hours Free Cancellation
5.0 (2)
from
$160
Mykonos Catamaran Sunset Semi private Cruise with transfer

Although not a day trip, this experience provides the perfect ending to a day in beautiful Mykonos. Set sail towards the horizon, with a glass …More

Mykonos, Greece

Although not a day trip, this experience provides the perfect ending to a day in beautiful Mykonos. Set sail towards the horizon, with a glass...

4 hours Free Cancellation
5.0 (19)
from
$159
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
$159
All inclusive Delos & Rhenia Islands tour (free transportation)

What makes our product unique is the contact with sea & sun. Sailing away with Nadia K, you will have the opportunity to experience new …More

Mykonos, Greece

What makes our product unique is the contact with sea & sun. Sailing away with Nadia K, you will have the opportunity to experience new...

6 hours Hotel pickup offered Free Cancellation
4.9 (239)
from
$157
Small group,swim in Rhenia,watch the sunset fm LVenice, freetrans

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice, …More

Mykonos, Greece

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice,...

4 to 5 hours Hotel pickup offered Free Cancellation
4.6 (28)
from
$155
Santorini Semi-private Morning or Sunset Volcano Sailing Tour

Book your Santorini sailing tour to explore the volcano, hot springs, stunning views, and local flavors! …More

Santorini, Greece

Book your Santorini sailing tour to explore the volcano, hot springs, stunning views, and local flavors!...

5 hours Free Cancellation
5.0 (22)
from
$154
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 Private Sailing Boat Cruise with Beneteau Oceanis 46.1

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number …More

Santorini, Greece

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number...

5 hours Hotel pickup offered Free Cancellation
5.0 (17)
from
$149
Santorini Luxury Catamaran Day Cruise with BBQ,drinks,transfer

A sailing trip is 'a must do' experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most …More

Santorini, Greece

A sailing trip is 'a must do' experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most...

5 hours Hotel pickup offered Free Cancellation
4.9 (213)
from
$148
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 (7,655)
from
$148
Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer)

Choose this half-day sailing cruise. Your tour begins with convenient transportation from your accommodation or the closest accessible point. At the embarkation dock, you meet …More

Santorini, Greece

Choose this half-day sailing cruise. Your tour begins with convenient transportation from your accommodation or the closest accessible point. At the embarkation dock, you meet...

5 hours Hotel pickup offered Free Cancellation
4.9 (222)
from
$148
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
$144
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
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
Morning Caldera Sailing Cruise

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

Santorini, Greece

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

5 hours Hotel pickup offered Free Cancellation
5.0 (36)
from
$144
Private 5h Cruise Catamaran Santorini BBQ,drinks, transfer

You will be able to admire the beauty of the cruise around santorini and within the several location we will be stopping at. Enjoy a …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

You will be able to admire the beauty of the cruise around santorini and within the several location we will be stopping at. Enjoy a...

5 hours Hotel pickup offered Free Cancellation
4.9 (7)
from
$143
Sunset Caldera Sailing Cruise

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 …More

Santorini, Greece

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...

5 hours Hotel pickup offered Free Cancellation
4.9 (87)
from
$143
Mykonos Catamaran Sunset Cruise with Meal, Drinks & Transfer

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches …More

Mykonos, Greece

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches...

4 hours Hotel pickup offered Free Cancellation
4.9 (127)
from
$142
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

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