Top Cyclades Islands Sailing Trips

Q: Which Cyclades Islands Sailing Trips have Instant Confirmation?

Cyclades Islands Sailing Trips with Instant Confirmation include: Santorini Volcano Hot Springs Santorini - Volcano and Hot springs Santorini Volcano and Hot Springs Cruise Tour from Fira Old Port Santorini 3 Islands Trip by Sailing boat Santorini 3 Islands Trip Sailing Wooden Boat View all Tours with Instant Confirmation →

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 →

Santorini: Small Group Catamaran Cruise with BBQ Fish & Drinks

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

Santorini, Greece

4.9 (71)

Santorini: Small Group Catamaran Cruise with BBQ Fish & Drinks

The Day and Sunset Luxury 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

4.9 (71)

from
$131

Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

Visit with licensed guide the natural insular archaeological site of Delos and enjoy swimming and snorkeling to a secluded cove off the uninhabited island of …More

Mykonos, Greece

4.7 (585)

Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

Visit with licensed guide the natural insular archaeological site of Delos and enjoy swimming and snorkeling to a secluded cove off the uninhabited island of...

5 to 6 hours Free Cancellation

4.7 (585)

from
$131

Mykonos Sunset Cruise to Rhenia, 3D Self-Tour of Delos, Dinner

Set the sails to the wind on afternoon sailing yacht cruise to Delos and Rhenia Islands. Bring the rich history of Delos back to life …More

Mykonos, Greece

4.9 (99)

Mykonos Sunset Cruise to Rhenia, 3D Self-Tour of Delos, Dinner

Set the sails to the wind on afternoon sailing yacht cruise to Delos and Rhenia Islands. Bring the rich history of Delos back to life...

5 hours Free Cancellation

4.9 (99)

from
$131

All inclusive cruise-Mykonos Delos&Rhenia beaches(free transport)

Experience the Joy of Sailing on a Yacht in a Friendly Small Group Atmosphere. Swim and Snorkel in Crystal Clear Waters, Indulge on Pristine Beaches …More

Mykonos, Greece

4.6 (122)

All inclusive cruise-Mykonos Delos&Rhenia beaches(free transport)

Experience the Joy of Sailing on a Yacht in a Friendly Small Group Atmosphere. Swim and Snorkel in Crystal Clear Waters, Indulge on Pristine Beaches...

6 hours Free Cancellation

4.6 (122)

from
$132

All inclusive Sunset Cruise Delos & Rhenia&swimming stop

Enjoy Sailing on the yacht in a friendly small group atmosphere. Swim and snorkel in crystal clear waters and indulge on the pristine beaches of …More

Mykonos, Greece

4.0 (4)

All inclusive Sunset Cruise Delos & Rhenia&swimming stop

Enjoy Sailing on the yacht in a friendly small group atmosphere. Swim and snorkel in crystal clear waters and indulge on the pristine beaches of...

4 hours Free Cancellation

4.0 (4)

from
$132

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

Mykonos, Greece

4.9 (1,192)

Mykonos: Brand-New Catamaran Cruise with Meal, Drinks & Transport

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

5 hours Hotel pickup offered Free Cancellation

4.9 (1,192)

from
$135

Sunset cruise to Rhenia& Little Venice with transfer

Although not a day trip, this experience provides the perfect ending to a day in beautiful Mykonos. Set sail towards the horizon, with a glass …More

Mykonos, Greece

4.9 (20)

Sunset cruise to Rhenia& Little Venice with transfer

Although not a day trip, this experience provides the perfect ending to a day in beautiful Mykonos. Set sail towards the horizon, with a glass...

4 hours Hotel pickup offered Free Cancellation

4.9 (20)

from
$136

6 Hours Tour to Delos and Rhenia Islands with Sailing Yacht

Leave the crowds on Mykonos behind and catch the wind with this sailing cruise to two nearby Aegean islands. Set sail from Tourlos Bay with …More

Mykonos, Greece

5.0 (14)

6 Hours Tour to Delos and Rhenia Islands with Sailing Yacht

Leave the crowds on Mykonos behind and catch the wind with this sailing cruise to two nearby Aegean islands. Set sail from Tourlos Bay with...

6 hours Hotel pickup offered Free Cancellation

5.0 (14)

from
$137

Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

Santorini's notorious Dream Catcher tour lets you experience with a small group, the beauty of Santorini and the magic of sailing in the Caldera with the …More

Santorini, Greece

4.9 (710)

Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

Santorini's notorious Dream Catcher tour lets you experience with a small group, the beauty of Santorini and the magic of sailing in the Caldera with the...

5 hours Hotel pickup offered Free Cancellation

4.9 (710)

from
$138

Mykonos Catamaran Sunset Cruise with Meal, Drinks & Transfer

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches …More

Mykonos, Greece

4.9 (127)

Mykonos Catamaran Sunset Cruise with Meal, Drinks & Transfer

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches...

4 hours Hotel pickup offered Free Cancellation

4.9 (127)

from
$142

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

4.9 (7)

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...

5 hours Hotel pickup offered Free Cancellation

4.9 (7)

from
$143

Milos and Polyaigos Full Day Cruise with Meals and Snorkelling

For those who wish to explore and learn everything about Milos island, this cruise will gratify you! Circumnavigate the island of Milos and visit the …More

Milos, Greece

4.9 (370)

Milos and Polyaigos Full Day Cruise with Meals and Snorkelling

For those who wish to explore and learn everything about Milos island, this cruise will gratify you! Circumnavigate the island of Milos and visit the...

9 to 10 hours Free Cancellation

4.9 (370)

from
$144

Mykonos Sail Cruise to Delos and Rhenia Islands

Hop on board and live a unique cruise experience in Mykonos island. Sail to the ancient Delos, explore this UNESCO World Heritage site, swim in …More

Mykonos, Greece

4.9 (666)

Mykonos Sail Cruise to Delos and Rhenia Islands

Hop on board and live a unique cruise experience in Mykonos island. Sail to the ancient Delos, explore this UNESCO World Heritage site, swim in...

6 hours Free Cancellation

4.9 (666)

from
$144

Captain Yiannis and his crew -all experienced sailors- can assure you that all claims about greek hospitality are true and that this cruise will be …More

Santorini, Greece

4.9 (87)

Sunset Caldera Sailing Cruise

Captain Yiannis and his crew -all experienced sailors- can assure you that all claims about greek hospitality are true and that this cruise will be...

5 hours Hotel pickup offered Free Cancellation

4.9 (87)

from
$144

Step aboard this 5 hour morning cruise for a relaxed sail and enjoy your time swimming, sunbathing, snorkeling, taking photos, tasting delicious BBQ meals, Greek …More

Santorini, Greece

5.0 (36)

Morning Caldera Sailing Cruise

Step aboard this 5 hour morning cruise for a relaxed sail and enjoy your time swimming, sunbathing, snorkeling, taking photos, tasting delicious BBQ meals, Greek...

5 hours Hotel pickup offered Free Cancellation

5.0 (36)

from
$144

Santorini Private Catamaran Cruise with BBQ, Open Bar & 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

5.0 (452)

Santorini Private Catamaran Cruise with BBQ, Open Bar & 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 Hotel pickup offered Free Cancellation

5.0 (452)

from
$146

Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer

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

5.0 (7,653)

Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer

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

5.0 (7,653)

from
$148

Santorini Luxury Catamaran Day Cruise with BBQ,drinks,transfer

A sailing trip is 'a must do' experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most …More

Santorini, Greece

4.9 (213)

Santorini Luxury Catamaran Day Cruise with BBQ,drinks,transfer

A sailing trip is 'a must do' experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most...

5 hours Hotel pickup offered Free Cancellation

4.9 (213)

from
$148

Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer)

Choose this half-day sailing cruise. Your tour begins with convenient transportation from your accommodation or the closest accessible point. At the embarkation dock, you meet …More

Santorini, Greece

4.9 (222)

Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer)

Choose this half-day sailing cruise. Your tour begins with convenient transportation from your accommodation or the closest accessible point. At the embarkation dock, you meet...

5 hours Hotel pickup offered Free Cancellation

4.9 (222)

from
$148

Santorini Semi-private Morning or Sunset Volcano Sailing Tour

Book your Santorini sailing tour to explore the volcano, hot springs, stunning views, and local flavors! …More

Santorini, Greece

5.0 (22)

Santorini Semi-private Morning or Sunset Volcano Sailing Tour

Book your Santorini sailing tour to explore the volcano, hot springs, stunning views, and local flavors!...

5 hours Free Cancellation

5.0 (22)

from
$154

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?

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

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

Which Cyclades Islands Sailing Trips have 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?