Cyclades Islands Sailing Trips

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
$3,329
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
$183
Half day Private Sailing cruise in Santorini island up to 6 pax

Enjoy the cruise like a real sailor and experience moving with the force of the wind! Maria our captain will stand our, together with our …More

Santorini, Greece

Enjoy the cruise like a real sailor and experience moving with the force of the wind! Maria our captain will stand our, together with our...

5 hours Free Cancellation
5.0 (6)
from
$1,033
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

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
$144
Full Day Tour to Kleftiko, Firlingos and Poliegos Catamaran

Sailing across the coastline, we will pass by the traditional fishing villages of Skinopi, Klima with the colorful little houses – called “Sirmata”- built by …More

Milos, Greece

Sailing across the coastline, we will pass by the traditional fishing villages of Skinopi, Klima with the colorful little houses – called “Sirmata”- built by...

10 hours Free Cancellation
5.0 (7)
from
$223
Private Half Day Morning Cruise of Milos and Kleftiko

This private sailing cruise offers a premium, all-inclusive experience on a modern sailing yacht exclusively for you. With a dedicated captain and hostess on board, …More

Milos, Greece

This private sailing cruise offers a premium, all-inclusive experience on a modern sailing yacht exclusively for you. With a dedicated captain and hostess on board,...

6 hours 30 minutes Free Cancellation
5.0 (8)
from
$1,712
Private Cruise All Around Of Milos & Sunset to Klima Village

“Our private ‘All Around Milos & Sunset’ cruise is the perfect way to explore the island at your own pace. With your own captain and …More

Milos, Greece

“Our private ‘All Around Milos & Sunset’ cruise is the perfect way to explore the island at your own pace. With your own captain and...

12 hours Free Cancellation
5.0 (6)
from
$1,714
Santorini Private Tour Half-Day Sailing Platinum Catamaran Cruise

This tour provides a complete experience of Santorini! You can swim in unique and otherwise impassable locations, enjoying the most wonderful of vistas while sailing …More

Santorini, Greece

This tour provides a complete experience of Santorini! You can swim in unique and otherwise impassable locations, enjoying the most wonderful of vistas while sailing...

5 hours Hotel pickup offered Free Cancellation
4.9 (9)
from
$236
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
$183
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
Luxury Private Power Catamaran Tour in Santorini

This is not a cookie-cutter approach to cruise sailing! Make your own schedule with us and choose the places you wish to see! Lucky 8 …More

Santorini, Greece

This is not a cookie-cutter approach to cruise sailing! Make your own schedule with us and choose the places you wish to see! Lucky 8...

3 hours
5.0 (7)
from
$1,837
Agios Georgios | Greek Traditional Wooden Boat

Daily Morning Shared Cruise Full-day cruise to Blue Lagoon, Despotiko and a secluded bay: First stop: Greek dakos with local wine Second stop: BBQ onboard, …More

Paros, Greece

Daily Morning Shared Cruise Full-day cruise to Blue Lagoon, Despotiko and a secluded bay: First stop: Greek dakos with local wine Second stop: BBQ onboard,...

7 hours 30 minutes Free Cancellation
5.0 (6)
from
$113
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
One Full Day of True Sailing to South Naxos & Koufonisi SY AGERAS

We sail from Piso Livadi towards South Naxos by 09:00, hoisting our sails & adjusting our course according to the prevailing winds we enjoy a …More

Paros, Greece

We sail from Piso Livadi towards South Naxos by 09:00, hoisting our sails & adjusting our course according to the prevailing winds we enjoy a...

10 hours Free Cancellation
5.0 (8)
from
$205
Katerina Sailing Sunrise and Sunset Cruises

Katerina Sailing Boat Milos is a family-run sailing experience offering authentic and intimate trips around the island of Milos. With Captain Katerina at the helm, …More

Milos, Greece

Katerina Sailing Boat Milos is a family-run sailing experience offering authentic and intimate trips around the island of Milos. With Captain Katerina at the helm,...

6 to 8 hours Free Cancellation
5.0 (9)
from
$1,141
Boat and hike tour to the Hidden Beaches of Syros

Our adventure begins at Kini, a charming fishing village on Syros' west coast. We board a boat and leave behind everyday life, cruising toward the …More

Syros, Greece

Our adventure begins at Kini, a charming fishing village on Syros' west coast. We board a boat and leave behind everyday life, cruising toward the...

5 hours Free Cancellation
5.0 (7)
from
$103
Private 2 Hours Sunset Cruise in Milos — Magical Klima Village

Heading to Klima promises not just a glimpse but a full immersion in nature's canvas at sunset. The way hues blend and dance across the …More

Milos, Greece

Heading to Klima promises not just a glimpse but a full immersion in nature's canvas at sunset. The way hues blend and dance across the...

2 hours Free Cancellation
5.0 (3)
from
$534
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
Santorini 3 Islands Trip by Sailing boat

Enjoy the classic tour trusted by thousands of visitors to Santorini for decades. Ideal for cruise travelers, as the boat tour begins at the port …More

Santorini, Greece

Enjoy the classic tour trusted by thousands of visitors to Santorini for decades. Ideal for cruise travelers, as the boat tour begins at the port...

5 hours 30 minutes Free Cancellation
4.5 (8)
from
$40
Private Boat Tour in Milos with Lunch

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

Milos, Greece

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

6 to 10 hours Free Cancellation
5.0 (4)
from
$1,826
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

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