Top Cyclades Islands Sailing Trips

153 Results
EXPLORE - Tour Adventure Koufonisia & Naxos (Private max 10 Pax)

From Paros Piso Livadi Port - Exclusive Private Sailing Adventure Around the Koufonisia Archipelago and Naxos. Enjoy an exclusive sailing trip through the stunning waters …More

Paros, Greece

From Paros Piso Livadi Port - Exclusive Private Sailing Adventure Around the Koufonisia Archipelago and Naxos. Enjoy an exclusive sailing trip through the stunning waters...

9 hours Free Cancellation
5.0 (1)
from
$1,930
DISCOVER - Tour Iraklia, Schinoussa & Naxos (Private max 10 Pax)

Immerse Yourself in the Beauty of the Small Cyclades Breathe in the fresh Aegean air and embrace the tranquility of the Small Cyclades. On this …More

Paros, Greece

Immerse Yourself in the Beauty of the Small Cyclades Breathe in the fresh Aegean air and embrace the tranquility of the Small Cyclades. On this...

9 hours Free Cancellation
from
$1,930
Mykonos Catamaran Private Delos Rhenia cruise

Indulge in this daily cruise to Delos and Rhenia islands, which lets you bask in the warm Mykonian sun, enjoying the summer breeze as you …More

Mykonos, Greece

Indulge in this daily cruise to Delos and Rhenia islands, which lets you bask in the warm Mykonian sun, enjoying the summer breeze as you...

6 hours Free Cancellation
4.9 (7)
from
$2,054
Private Cruise West Side of Milo's & Kleftiko

Our "West Side of Milos & Kleftiko" cruise offers a unique blend of natural beauty, historical exploration, and relaxation. Enjoy the privacy of the yacht …More

Milos, Greece

Our "West Side of Milos & Kleftiko" cruise offers a unique blend of natural beauty, historical exploration, and relaxation. Enjoy the privacy of the yacht...

7 hours 30 minutes Free Cancellation
5.0 (2)
from
$2,066
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
Private Rhenia sailing cruise with Lunch & Transfer

Our team is highly qualified, with years of experience in the Greek waters; they are our home. Over the last decades, our business has included …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Our team is highly qualified, with years of experience in the Greek waters; they are our home. Over the last decades, our business has included...

6 hours Hotel pickup offered Free Cancellation
5.0 (3)
from
$2,227
Santorini Private Cruise to Volcanic Islands and Hot Springs

Sailing along the cliff at the north beautiful part of Santorini passing from Fira town - Imerovigli - Oia - Ammoudi - Thirassia - Volcano …More

Santorini, Greece

Sailing along the cliff at the north beautiful part of Santorini passing from Fira town - Imerovigli - Oia - Ammoudi - Thirassia - Volcano...

4 hours 30 minutes Hotel pickup offered Free Cancellation
from
$2,296
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
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
Milos Private Half-Day Catamaran Cruise to Kleftiko with Lunch

Experience a private half-day cruise from Adamantas to Kleftiko aboard a luxurious sailing catamaran. Perfect for family, friends, special celebrations, with activities, dining, & breathtaking …More

Milos, Greece

Experience a private half-day cruise from Adamantas to Kleftiko aboard a luxurious sailing catamaran. Perfect for family, friends, special celebrations, with activities, dining, & breathtaking...

5 hours 30 minutes Free Cancellation
5.0 (4)
from
$2,755
2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos

This cruise is unique and a must when visiting Milos. It gives visitors the opportunity to experience a night on-board a 13m sailing boat and …More

Milos, Greece

This cruise is unique and a must when visiting Milos. It gives visitors the opportunity to experience a night on-board a 13m sailing boat and...

2 days Free Cancellation
5.0 (10)
from
$2,769
Milos Private Full Day Catamaran Cruise with Lunch and Drinks

Set sail on a private full-day cruise aboard a luxurious sailing catamaran from Adamantas Port, Milos, for an unforgettable journey to Kleftiko Bay and Polyegos …More

Milos, Greece

Set sail on a private full-day cruise aboard a luxurious sailing catamaran from Adamantas Port, Milos, for an unforgettable journey to Kleftiko Bay and Polyegos...

9 hours Free Cancellation
5.0 (10)
from
$3,292
Island Hopping: Santorini Catamaran Charter Cruise with a skipper

Design your own trip and explore the Aegean! Feel free to craft your own personalized sailing route. We are ready to make it happen. Set …More

Paros, Greece

Design your own trip and explore the Aegean! Feel free to craft your own personalized sailing route. We are ready to make it happen. Set...

7 days
4.9 (123)
from
$8,450

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