Cyclades Islands Sailing Trips

153 Results
Santorini: Small Group Catamaran Cruise with BBQ Fish & Drinks

The Day and Sunset Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

The Day and Sunset Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a...

5 hours Hotel pickup offered Free Cancellation
4.9 (71)
from
$125
All inclusive cruise-Mykonos Delos&Rhenia beaches(free transport)

Experience the Joy of Sailing on a Yacht in a Friendly Small Group Atmosphere. Swim and Snorkel in Crystal Clear Waters, Indulge on Pristine Beaches …More

Mykonos, Greece

Experience the Joy of Sailing on a Yacht in a Friendly Small Group Atmosphere. Swim and Snorkel in Crystal Clear Waters, Indulge on Pristine Beaches...

6 hours Free Cancellation
4.6 (122)
from
$130
All inclusive Sunset Cruise Delos & Rhenia&swimming stop

Enjoy Sailing on the yacht in a friendly small group atmosphere. Swim and snorkel in crystal clear waters and indulge on the pristine beaches of …More

Mykonos, Greece

Enjoy Sailing on the yacht in a friendly small group atmosphere. Swim and snorkel in crystal clear waters and indulge on the pristine beaches of...

4 hours Free Cancellation
4.0 (4)
from
$130
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 (1,192)
from
$134
6 Hours Tour to Delos and Rhenia Islands with Sailing Yacht

Leave the crowds on Mykonos behind and catch the wind with this sailing cruise to two nearby Aegean islands. Set sail from Tourlos Bay with …More

Mykonos, Greece

Leave the crowds on Mykonos behind and catch the wind with this sailing cruise to two nearby Aegean islands. Set sail from Tourlos Bay with...

6 hours Hotel pickup offered Free Cancellation
5.0 (14)
from
$134
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
$135
Sunset cruise to Rhenia& Little Venice 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

Likely to Sell Out
Likely to Sell Out
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 Hotel pickup offered Free Cancellation
4.9 (20)
from
$135
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
$141
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
$141
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
$141
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
$141
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
$141
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
$142
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
$143
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 (7,659)
from
$146
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
$146
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
$147
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
$148
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
$152
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
$152
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
$152

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These answers are based on answers previously given to Key West Private Charters customers' questions.

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