Cyclades Islands Sailing Trips

149 Results
Milos Sunset Catamaran Cruise to Kleftiko Bay with Meal & Drinks

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge, …More

Milos, Greece

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge,...

5 hours 30 minutes Free Cancellation
5.0 (32)
from
$177
Glaraki Private Day Cruise

Our cruise starts with a delicious breakfast enjoyed on board while heading towards our first destination, Panteronisia / Blue Lagoon.  Once there, we will be surrounded …More

Antiparos, Greece

Our cruise starts with a delicious breakfast enjoyed on board while heading towards our first destination, Panteronisia / Blue Lagoon.  Once there, we will be surrounded...

6 hours 45 minutes Free Cancellation
5.0 (31)
from
$1,837
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
Catamaran Half Day Afternoon Cruise With Sunset: Kleftiko

Enjoy amazing moments in Milos island! An ideal cruise for you in order to see the most famous spots here in Milos such as Kleftiko …More

Milos, Greece

Enjoy amazing moments in Milos island! An ideal cruise for you in order to see the most famous spots here in Milos such as Kleftiko...

6 hours Free Cancellation
4.9 (28)
from
$166
Semi-Private Half Day/Sunset cruise

Choose Your Perfect Half-Day Cruise Experience Enjoy a unique escape on the sea with one of our three half-day cruises Morning Cruise – 09:30 to …More

Paros, Greece

Choose Your Perfect Half-Day Cruise Experience Enjoy a unique escape on the sea with one of our three half-day cruises Morning Cruise – 09:30 to...

3 hours Free Cancellation
4.9 (26)
from
$103
Milos Luxury Catamaran Cruise to Kleftiko Bay with Lunch

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge, …More

Milos, Greece

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge,...

5 hours 30 minutes Free Cancellation
5.0 (22)
from
$178
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
All inclusive cruise Sailing Cruise to Delos&Rhenia beaches

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...

5 hours 30 minutes Free Cancellation
4.8 (22)
from
$121
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
$136
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
Private full day cruise to Antiparos with Paros Sail

You came to your vacation in Paros, there is one thing you must do! Sail and swim in the Blue Lagoon and all the places …More

Paros, Greece

You came to your vacation in Paros, there is one thing you must do! Sail and swim in the Blue Lagoon and all the places...

7 hours Free Cancellation
5.0 (20)
from
$2,441
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
Santorini Volcano Hot Springs

Visit Volcano & Hot Springs by joining our most popular & low cost tour. An experience you don't want to miss! ideal for cruise travelers, …More

Santorini, Greece

Visit Volcano & Hot Springs by joining our most popular & low cost tour. An experience you don't want to miss! ideal for cruise travelers,...

3 hours Free Cancellation
4.8 (18)
from
$34
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
$183
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
$262
Full Day Santorini Catamaran Private Cruise with meal and transfer

Booking a Private Catamaran Tour in Santorini is a dream come true! We offer daily cruises to Santorini’s beautiful sights. The best way to spend …More

Santorini, Greece

Booking a Private Catamaran Tour in Santorini is a dream come true! We offer daily cruises to Santorini’s beautiful sights. The best way to spend...

7 hours Hotel pickup offered
5.0 (16)
from
$2,526
Mykonos Catamaran Cruise with Meal Drinks and Sup

Go on a half-day cruise in the Aegean Sea. Select your preferred departure time morning or afternoon and sail to the mythical Delos and Rhenia …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Go on a half-day cruise in the Aegean Sea. Select your preferred departure time morning or afternoon and sail to the mythical Delos and Rhenia...

5 hours Free Cancellation
4.9 (14)
from
$1,370
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
$137
All inclusive Private Cruise: Delos &Rhenia island

A full day of fun, culture and culinary discovery. Spend a perfect day out on the sea combining a relaxing sailing cruise, swimming and sunbathing …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

A full day of fun, culture and culinary discovery. Spend a perfect day out on the sea combining a relaxing sailing cruise, swimming and sunbathing...

6 hours Free Cancellation
5.0 (13)
from
$69
Santorini Private Cruise Sightseeing Tour with BBQ and Drinks

Enjoy swimming & snorkeling in the clear blue waters of the Aegean Sea. You can go snorkeling near the shore and experience the amazing underwater …More

Santorini, Greece

Enjoy swimming & snorkeling in the clear blue waters of the Aegean Sea. You can go snorkeling near the shore and experience the amazing underwater...

5 hours Free Cancellation
5.0 (13)
from
$170
Private sailing cruise to Delos & Rhenia with Lunch & Transfer

Our first stop is an hour away, the renowned Big Delos island. While there, you will have the opportunity to visit one of the most …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Our first stop is an hour away, the renowned Big Delos island. While there, you will have the opportunity to visit one of the most...

6 hours Hotel pickup offered Free Cancellation
5.0 (12)
from
$2,227

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