Top Cyclades Islands Sailing Trips

153 Results
Half Day Catamaran Afternoon Cruise in Kleftiko

The Half day afternoon cruise will remain etched in your mind until you repeat it. Enjoy the natural beauties and the incredible variety of rocks, …More

Milos, Greece

The Half day afternoon cruise will remain etched in your mind until you repeat it. Enjoy the natural beauties and the incredible variety of rocks,...

6 hours Free Cancellation
5.0 (1)
from
$177
Luxury Small-Group Catamaran Cruise with BBQ, Open bar & Transfer

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Ammoudi Bay or Vlychada Marina. Sail past the island's highlights, such as the Red …More

Santorini, Greece

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Ammoudi Bay or Vlychada Marina. Sail past the island's highlights, such as the Red...

5 hours Free Cancellation
4.9 (953)
from
$182
Milos Small-Group Full-Day Cruise with Snorkelling and Lunch

The cruise is done at a relaxed pace, trying to avoid crowds with only 12 passengers aboard the sailing boat. Boats are equipped with large …More

Milos, Greece

The cruise is done at a relaxed pace, trying to avoid crowds with only 12 passengers aboard the sailing boat. Boats are equipped with large...

8 hours Free Cancellation
5.0 (1,552)
from
$182
Full Day Boat Tour Around Milos and Poliegos

Every side of the island has complete different things to offer you! There are caves and stories about pirates . There are huge piles of …More

Milos, Greece

Every side of the island has complete different things to offer you! There are caves and stories about pirates . There are huge piles of...

10 hours Free Cancellation
4.8 (8)
from
$182
Full Day Boat Tour to Kleftiko & Sykia Cave

Our special trip is a full day tour gift to the soul, as you have the chance to witness virial historical monuments, by the sea, …More

Milos, Greece

Our special trip is a full day tour gift to the soul, as you have the chance to witness virial historical monuments, by the sea,...

8 hours Free Cancellation
5.0 (6)
from
$182
Round of Milos and Poliegos Sailing boat snorkelling cruise

Set sail for a day and enjoy an unforgettable experience at sea circumnavigating Milos, passing by its highlights, and visiting Poliegos and its fantastic waters. …More

Milos, Greece

Set sail for a day and enjoy an unforgettable experience at sea circumnavigating Milos, passing by its highlights, and visiting Poliegos and its fantastic waters....

9 hours Free Cancellation
5.0 (322)
from
$182
Luxury Catamaran Semi private cruise with meals & drinks and transportation.

Take a break from the resort crowds and get offshore for a while on this chilled-out sailing excursion around Mykonos. Choose a trip to the …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Take a break from the resort crowds and get offshore for a while on this chilled-out sailing excursion around Mykonos. Choose a trip to the...

5 hours Hotel pickup offered Free Cancellation
4.5 (42)
from
$182
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
Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

Experience the beauty of Santorini and its volcanic caldera on this small-group sailing tour. Cruise by some of the island’s best-known landmarks before venturing into …More

Santorini, Greece

Experience the beauty of Santorini and its volcanic caldera on this small-group sailing tour. Cruise by some of the island’s best-known landmarks before venturing into...

5 hours Hotel pickup offered Free Cancellation
4.9 (286)
from
$184
Santorini Private Catamaran Cruise

A Lagoon catamaran for your group only: up to 20 guests, 5 hours by day or at sunset from Vlychada Marina. Sail past Red Beach …More

Santorini, Greece

A Lagoon catamaran for your group only: up to 20 guests, 5 hours by day or at sunset from Vlychada Marina. Sail past Red Beach...

5 hours Hotel pickup offered Free Cancellation
5.0 (40)
from
$184
Sailboat Full Day Tour in Kleftiko and Blue Lagoon with Lunch

Make this day unique, forget about any distraction while onboard. Enjoy a genuine adventure that will remain unforgettable. Take some stunning photos and videos that …More

Milos, Greece

Make this day unique, forget about any distraction while onboard. Enjoy a genuine adventure that will remain unforgettable. Take some stunning photos and videos that...

9 hours Free Cancellation
5.0 (55)
from
$188
Catamaran Half Day Morning Cruise: Kleftiko

Enjoy a half-day cruise and discover the most beautiful places in Milos sailing on the West and South side of the island, exploring the caves …More

Milos, Greece

Enjoy a half-day cruise and discover the most beautiful places in Milos sailing on the West and South side of the island, exploring the caves...

6 hours Free Cancellation
4.9 (197)
from
$189
DISCOVER - Iraklia, Schinoussa & Naxos (Shared max 10 People)

You will feel the smell of the Aegean Sea and breeze, and enjoy the relaxing beauty of the small Cyclades. During your full-day sailing trip, …More

Paros, Greece

You will feel the smell of the Aegean Sea and breeze, and enjoy the relaxing beauty of the small Cyclades. During your full-day sailing trip,...

10 hours Free Cancellation
4.7 (25)
from
$193
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
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
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
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
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

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