Top Cyclades Islands Sailing Trips

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 →

5 Hours Sailing Trip to Mykonos Famous Beaches with Lunch

The opportunity to see all South beaches, soak up the sun, snorkel to crystal clear waters, and meet new people. The opportunity to explore the …More

Mykonos, Greece

5.0 (33)

5 Hours Sailing Trip to Mykonos Famous Beaches with Lunch

The opportunity to see all South beaches, soak up the sun, snorkel to crystal clear waters, and meet new people. The opportunity to explore the...

5 hours Hotel pickup offered Free Cancellation

5.0 (33)

from
$120

Santorini Oia: Small Group Day Cruise w BBQ Fresh Fish & Drinks

The Day Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay, is a great opportunity to enjoy a sailing cruise …More

Santorini, Greece

5.0 (33)

Santorini Oia: Small Group Day Cruise w BBQ Fresh Fish & Drinks

The Day Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay, is a great opportunity to enjoy a sailing cruise...

4 hours Hotel pickup offered Free Cancellation

5.0 (33)

from
$120

2-Day Santorini Bus Tour with Volcanic Cruise

See all of the best of Santorini in this 2-day tour, visiting all must-sees and experience the island's culture before you go back home. Explore …More

Santorini, Greece

5.0 (3)

2-Day Santorini Bus Tour with Volcanic Cruise

See all of the best of Santorini in this 2-day tour, visiting all must-sees and experience the island's culture before you go back home. Explore...

2 days Free Cancellation

5.0 (3)

from
$115

Morning and Sunset Cruise with Meal and Transport Included

Choose between a morning or sunset cruise when booking. On the day, depart from your hotel via air-conditioned minivan to Mykonos' new port for the …More

Mykonos, Greece

5.0 (6)

Morning and Sunset Cruise with Meal and Transport Included

Choose between a morning or sunset cruise when booking. On the day, depart from your hotel via air-conditioned minivan to Mykonos' new port for the...

5 hours Free Cancellation

5.0 (6)

from
$114

3-Hour Mykonos Best Beaches Yacht Cruise

Discover Mykonos from a different perspective aboard a sailing yacht and cruise along the island's world-famous south coast. This small-group experience is limited to just …More

Mykonos, Greece

5.0 (2)

3-Hour Mykonos Best Beaches Yacht Cruise

Discover Mykonos from a different perspective aboard a sailing yacht and cruise along the island's world-famous south coast. This small-group experience is limited to just...

3 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$114

South Coast Premium Sail Cruise with Lunch Drinks Swim and Sunset

This evening cruise is ideal for travelers that want to explore southern part of Mykonos passing through the worldwide famous bays, making couple of swimstops …More

Mykonos, Greece

4.9 (69)

South Coast Premium Sail Cruise with Lunch Drinks Swim and Sunset

This evening cruise is ideal for travelers that want to explore southern part of Mykonos passing through the worldwide famous bays, making couple of swimstops...

4 hours Free Cancellation

4.9 (69)

from
$114

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

Santorini: Caldera Classic Semi-Private Cruise with BBQ & Drinks

The Day and Sunset Classic Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a …More

Santorini, Greece

5.0 (86)

Santorini: Caldera Classic Semi-Private Cruise with BBQ & Drinks

The Day and Sunset Classic Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a...

5 hours Hotel pickup offered Free Cancellation

5.0 (86)

from
$108

Luxury Santorini Catamaran Cruise: Lunch, BBQ, Drinks, Transfers

Our Santorini day cruise starts from the picturesque port of Vlychada, sailing onwards to explore the beauty of the Red Beach, White Beach, Indian Rocks, …More

Santorini, Greece

5.0 (447)

Luxury Santorini Catamaran Cruise: Lunch, BBQ, Drinks, Transfers

Our Santorini day cruise starts from the picturesque port of Vlychada, sailing onwards to explore the beauty of the Red Beach, White Beach, Indian Rocks,...

5 hours Hotel pickup offered Free Cancellation

5.0 (447)

from
$103

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

Choose Your Perfect Half-Day Cruise Experience Enjoy a unique escape on the sea with one of our three half-day cruises Morning Cruise – 09:30 to …More

Paros, Greece

4.9 (26)

Semi-Private Half Day/Sunset cruise

Choose Your Perfect Half-Day Cruise Experience Enjoy a unique escape on the sea with one of our three half-day cruises Morning Cruise – 09:30 to...

3 hours Free Cancellation

4.9 (26)

from
$102

Sparkling seas and secluded beaches? Join our Rhenia – Delos cruise and live a day like no other! The Cycladic Sisters, Mykonos, Delos and Rhenia, …More

Mykonos, Greece

4.8 (432)

The Authentic Rhenia-Delos Cruise

Sparkling seas and secluded beaches? Join our Rhenia – Delos cruise and live a day like no other! The Cycladic Sisters, Mykonos, Delos and Rhenia,...

6 hours 30 minutes Free Cancellation

4.8 (432)

from
$102

Santorini Catamaran Cruise: with Lunch, BBQ, Open Bar, Transfers

Step aboard our catamaran with Santorini Yachting Cruises, and join us for an incredible sailing adventure! Our day cruise sets sail from the port of …More

Santorini, Greece

5.0 (309)

Santorini Catamaran Cruise: with Lunch, BBQ, Open Bar, Transfers

Step aboard our catamaran with Santorini Yachting Cruises, and join us for an incredible sailing adventure! Our day cruise sets sail from the port of...

5 hours Hotel pickup offered Free Cancellation

5.0 (309)

from
$98

Mykonos Half Day Cruise to Rhenia and Delos Islands with Meals

This cruise is perfect for lazy sleepers or people that have limited stay in Mykonos. During the half day cruise travellers would experience the joy …More

Mykonos, Greece

5.0 (2)

Mykonos Half Day Cruise to Rhenia and Delos Islands with Meals

This cruise is perfect for lazy sleepers or people that have limited stay in Mykonos. During the half day cruise travellers would experience the joy...

5 hours Free Cancellation

5.0 (2)

from
$98

Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers

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

Santorini, Greece

4.9 (3,725)

Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers

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

5 hours Free Cancellation

4.9 (3,725)

from
$92

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Enjoy a perfect sailing Sunset tour in the magnificent island of Santorini on board our catamaran. The catamaran sails to the most amazing sights of …More

Santorini, Greece

4.6 (1,021)

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Enjoy a perfect sailing Sunset tour in the magnificent island of Santorini on board our catamaran. The catamaran sails to the most amazing sights of...

5 hours Hotel pickup offered Free Cancellation

4.6 (1,021)

from
$90

Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer

Enjoy a perfect sailing 5-hour tour from the magnificent island of Santorini onboard the catamaran, sailing to the most amazing sights of Santorini such as …More

Santorini, Greece

4.8 (585)

Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer

Enjoy a perfect sailing 5-hour tour from the magnificent island of Santorini onboard the catamaran, sailing to the most amazing sights of Santorini such as...

5 hours Hotel pickup offered Free Cancellation

4.8 (585)

from
$90

3 Hours Private Sunset Tour in Greece with Free Drinks & Snacks

Close your eyes and create an image of setting sail towards the horizon with a glass of wine on hand, watching the sun dipping into …More

Mykonos, Greece

3.0 (2)

3 Hours Private Sunset Tour in Greece with Free Drinks & Snacks

Close your eyes and create an image of setting sail towards the horizon with a glass of wine on hand, watching the sun dipping into...

3 hours Hotel pickup offered Free Cancellation

3.0 (2)

from
$86

Shared Day Cruise to Little Venice & Agios Stefanos

Enjoy a most memorable cruise of the most popular highlights of Mykonos, Little Venice and Agios Stefanos. …More

Mykonos, Greece

5.0 (1)

Shared Day Cruise to Little Venice & Agios Stefanos

Enjoy a most memorable cruise of the most popular highlights of Mykonos, Little Venice and Agios Stefanos....

5 hours 30 minutes Free Cancellation

5.0 (1)

from
$80

A Boat Trip to the Pirate Caves & Blue Lagoon

Join this boat trip to the South Pirate Caves, where you will enjoy some local white wine and seasonal fruit and snorkelling in the very …More

Paros, Greece

4.9 (86)

A Boat Trip to the Pirate Caves & Blue Lagoon

Join this boat trip to the South Pirate Caves, where you will enjoy some local white wine and seasonal fruit and snorkelling in the very...

3 hours 30 minutes Free Cancellation

4.9 (86)

from
$74

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 Sailing Trips?

What are the best kid-friendly options for Cyclades Islands Sailing Trips Tours?

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

View all kid-friendly Tours →

Which Cyclades Islands Sailing Trips have Instant Confirmation?

Cyclades Islands Sailing Trips with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Cyclades Islands Sailing Trips have Free Cancellation?

Cyclades Islands Sailing Trips 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 Sailing Trips have Hotel Pickup?

No problem. These Cyclades Islands Sailing Trips 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?