Top Cyclades Islands Sailing Trips

153 Results
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
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
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
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
$183
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
$183
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
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 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
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
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
$176
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
$176
Santorini Fishing Private Cruise boat tour - BBQ, Snorkeling

The local captain “Makis” from “The Pirate fishing tours” in Santorini, loves to share his passion for the sea, with the visitors to Santorini island …More

Santorini, Greece

The local captain “Makis” from “The Pirate fishing tours” in Santorini, loves to share his passion for the sea, with the visitors to Santorini island...

5 hours Free Cancellation
5.0 (355)
from
$172
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
$172
Milos Sailing Tour with snorkeling and lunch

We start from Pollonia or Adamas and we explore beautiful Milos and magnificent Kleftiko • Comfort and luxury: Our boat features 4 double cabins and …More

Milos, Greece

We start from Pollonia or Adamas and we explore beautiful Milos and magnificent Kleftiko • Comfort and luxury: Our boat features 4 double cabins and...

8 hours Free Cancellation
4.8 (196)
from
$171
Mykonos: Luxury Catamaran Cruise with Meal, Drinks & Transport

Cruise with Nostos Mykonos Yachts in sophisticated chic style and discover the gorgeous nearby island of Rhenia or the famous Mykonian southern coast (itinerary is …More

Mykonos, Greece

Cruise with Nostos Mykonos Yachts in sophisticated chic style and discover the gorgeous nearby island of Rhenia or the famous Mykonian southern coast (itinerary is...

5 hours Hotel pickup offered Free Cancellation
4.9 (10)
from
$171
Mykonos 6hrs sailing cruise: Delos Rhenia with lunch & transfer

We setsail at 09:00am from Tourlos Marina. Our first stop is an hour away, the renowned Big Delos island. While there, you will have the …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

We setsail at 09:00am from Tourlos Marina. Our first stop is an hour away, the renowned Big Delos island. While there, you will have the...

6 hours Hotel pickup offered Free Cancellation
5.0 (98)
from
$170

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Discover Cyclades Islands