Top Cyclades Islands Cruises, Sailing & Water Tours

Q: Got any more Cyclades Islands trip ideas?

We sure do. Check out our curated lists of hand-picked Cyclades Islands Tours. Top 10 Cyclades Islands 2026 Senior-friendly tours Cyclades Islands The best tours and activities for culture lovers in Cyclades Islands Top Day Trips from Cyclades Islands Things to do in Cyclades Islands this summer View all Cyclades Islands Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Cyclades Islands?

Based on our sales data over the past year, the most popular styles of tours and activities in Cyclades Islands are: Cyclades Islands Luxury & Special Occasions Cyclades Islands Luxury Tours Cyclades Islands Tours & Sightseeing Cyclades Islands Half-day Tours Cyclades Islands Cruises, Sailing & Water Tours View all tour styles in Cyclades Islands →

Mykonos boat tour from Cruise Terminal-Small Group (new product)

In Mykonian spirit cruises we want to introduce you in the real mykonian way of life, a day away from the crowds of Mykonos town, …More

Mykonos, Greece

5.0 (5)

Mykonos boat tour from Cruise Terminal-Small Group (new product)

In Mykonian spirit cruises we want to introduce you in the real mykonian way of life, a day away from the crowds of Mykonos town,...

5 hours Free Cancellation

5.0 (5)

from
$204

7-Hour Private Speedboat Tour in Antiparos

Between Antiparos and Paros, two islands (Pateronissia) form a passage with waters that their color stands out even from an airplane. Famous tourist destination for …More

Paros, Greece

5.0 (8)

7-Hour Private Speedboat Tour in Antiparos

Between Antiparos and Paros, two islands (Pateronissia) form a passage with waters that their color stands out even from an airplane. Famous tourist destination for...

7 hours Free Cancellation

5.0 (8)

from
$141

Do not miss out! When in Santorini, the sunset and a sailing cruise around the Caldera, are the things one should not miss out. Have …More

Santorini, Greece

5.0 (5)

Caldera Private Cruise with Fjord 52

Do not miss out! When in Santorini, the sunset and a sailing cruise around the Caldera, are the things one should not miss out. Have...

5 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$254

5hours Private boat cruise tour in Santorini with lunch or dinner

Sail across the breathtaking Santorini Caldera on a private cruise designed for unforgettable moments. Discover hidden coves, swim in crystal-clear waters, and soak in the …More

Santorini, Greece

5.0 (8)

5hours Private boat cruise tour in Santorini with lunch or dinner

Sail across the breathtaking Santorini Caldera on a private cruise designed for unforgettable moments. Discover hidden coves, swim in crystal-clear waters, and soak in the...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$907

Santorini, Ios Full-Day Small-Group Catamaran Tour with Lunch

Set sail from Vlychada on a modern catamaran for a scenic tour, sailing along Red Beach, White Beach, the Volcano, Thirassia Island, and Ios. Anchoring …More

Santorini, Greece

5.0 (7)

Santorini, Ios Full-Day Small-Group Catamaran Tour with Lunch

Set sail from Vlychada on a modern catamaran for a scenic tour, sailing along Red Beach, White Beach, the Volcano, Thirassia Island, and Ios. Anchoring...

8 to 10 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$239

Discover the beauty of Mykonos and its hidden gems on an exclusive RIB boat cruise. Glide across the crystal-clear waters of the Aegean, visiting stunning …More

Mykonos, Greece

5.0 (9)

Mykonos Luxury Semi Private Cruise

Discover the beauty of Mykonos and its hidden gems on an exclusive RIB boat cruise. Glide across the crystal-clear waters of the Aegean, visiting stunning...

4 hours Free Cancellation

5.0 (9)

from
$1,249

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

5.0 (6)

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,...

7 hours 30 minutes Free Cancellation

5.0 (6)

from
$113

Explore Polyaigos on a Private Boat Tour

Embark on an unforgettable private boat tour to Polyaigos , the hidden gem of the Cyclades, nestled between Sifnos and Kimolos. Departing from Platis Gialos …More

5.0 (9)

Explore Polyaigos on a Private Boat Tour

Embark on an unforgettable private boat tour to Polyaigos , the hidden gem of the Cyclades, nestled between Sifnos and Kimolos. Departing from Platis Gialos...

4 hours Free Cancellation

5.0 (9)

from
$1,084

Mykonos Catamaran Cruise Day or Sunset Tour with Meals and Drinks

Enjoy a memorable cruise featuring a delicious meal prepared on board with fresh, local ingredients. Take a refreshing swim in crystal clear waters, then relax …More

Mykonos, Greece

4.7 (13)

Mykonos Catamaran Cruise Day or Sunset Tour with Meals and Drinks

Enjoy a memorable cruise featuring a delicious meal prepared on board with fresh, local ingredients. Take a refreshing swim in crystal clear waters, then relax...

5 hours Hotel pickup offered Free Cancellation

4.7 (13)

from
$207

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

4.9 (9)

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...

8 hours Free Cancellation

4.9 (9)

from
$194

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

5.0 (8)

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...

10 hours Free Cancellation

5.0 (8)

from
$222

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

5.0 (9)

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,...

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

5.0 (7)

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...

5 hours Free Cancellation

5.0 (7)

from
$103

Catamaran Private Tour in Mykonos with Transfer

Embark on a private cruise through Mykonos’ crystal-clear waters, designed just for you! Choose a morning adventure to explore famous beaches like Psarou, Ornos, and …More

Mykonos, Greece

5.0 (8)

Catamaran Private Tour in Mykonos with Transfer

Embark on a private cruise through Mykonos’ crystal-clear waters, designed just for you! Choose a morning adventure to explore famous beaches like Psarou, Ornos, and...

5 hours

5.0 (8)

from
$1,845

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

5.0 (3)

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...

2 hours Free Cancellation

5.0 (3)

from
$532

Our Sunset cruise will offer you the perfect way to end a beautiful day and begin a magical night. This exclusive experience offers a breathtaking …More

Paros, Greece

5.0 (2)

Private Sunset Cruise with Speedboat

Our Sunset cruise will offer you the perfect way to end a beautiful day and begin a magical night. This exclusive experience offers a breathtaking...

3 hours Free Cancellation

5.0 (2)

from
$68

Private Cruise: MYKONOS – KOUFONISIA – SCHINOUSA - HERAKLIA

Our private day cruise from Paros to Koufonisia – Schinousa – Heraklia (Small Cyclades), located south-east of Naxos Island, is a journey to the undiscovered …More

Mykonos, Greece

5.0 (2)

Private Cruise: MYKONOS – KOUFONISIA – SCHINOUSA - HERAKLIA

Our private day cruise from Paros to Koufonisia – Schinousa – Heraklia (Small Cyclades), located south-east of Naxos Island, is a journey to the undiscovered...

8 hours Free Cancellation

5.0 (2)

from
$3,310

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

5.0 (2)

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...

7 hours 30 minutes Free Cancellation

5.0 (2)

from
$2,070

Private Tour: Delos Day Trip from Mykonos

Discover the legends and beauty of Delos on a half-day tour, led by a private local guide. After a boat ride from Mykonos, explore the …More

Mykonos, Greece

5.0 (3)

Private Tour: Delos Day Trip from Mykonos

Discover the legends and beauty of Delos on a half-day tour, led by a private local guide. After a boat ride from Mykonos, explore the...

4 hours Hotel pickup offered

5.0 (3)

from
$259

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

4.5 (8)

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...

5 hours 30 minutes Free Cancellation

4.5 (8)

from
$40

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Cyclades Islands Cruises, Sailing & Water Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Cyclades Islands Cruises, Sailing & Water Tours are:

What are the best kid-friendly options for Cyclades Islands Cruises, Sailing & Water Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Cyclades Islands Cruises, Sailing & Water Tours are:

View all kid-friendly Tours →

Which Cyclades Islands Cruises, Sailing & Water Tours have Instant Confirmation?

Cyclades Islands Cruises, Sailing & Water Tours with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Cyclades Islands Cruises, Sailing & Water Tours have Free Cancellation?

Cyclades Islands Cruises, Sailing & Water Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Cyclades Islands Cruises, Sailing & Water Tours have Hotel Pickup?

No problem. These Cyclades Islands Cruises, Sailing & Water Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Cyclades Islands trip ideas?

What are the most popular styles of Tours and Activities in Cyclades Islands?