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 →

Catamaran Half Day Afternoon Cruise With Sunset: Kleftiko

Enjoy amazing moments in Milos island! An ideal cruise for you in order to see the most famous spots here in Milos such as Kleftiko …More

Milos, Greece

4.9 (28)

Catamaran Half Day Afternoon Cruise With Sunset: Kleftiko

Enjoy amazing moments in Milos island! An ideal cruise for you in order to see the most famous spots here in Milos such as Kleftiko...

6 hours Free Cancellation

4.9 (28)

from
$166

Half day Catamaran Morning Cruise in Kleftiko

We welcome you to the island of colors with its natural beauty and incredible rock formations, a unique destination for each of you.   Polychronis Mavros …More

Milos, Greece

5.0 (47)

Half day Catamaran Morning Cruise in Kleftiko

We welcome you to the island of colors with its natural beauty and incredible rock formations, a unique destination for each of you.   Polychronis Mavros...

6 hours Free Cancellation

5.0 (47)

from
$165

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

The Sunset Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay in Oia is a great opportunity to enjoy a …More

Santorini, Greece

5.0 (113)

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

The Sunset Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay in Oia is a great opportunity to enjoy a...

6 hours Hotel pickup offered Free Cancellation

5.0 (113)

from
$165

Santorini Oia: Private Day Cruise with Fresh Fish BBQ & Drinks

The Private Day Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay is a great opportunity to enjoy a sailing cruise at the …More

Santorini, Greece

5.0 (38)

Santorini Oia: Private Day Cruise with Fresh Fish BBQ & Drinks

The Private Day Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay is a great opportunity to enjoy a sailing cruise at the...

4 hours Hotel pickup offered Free Cancellation

5.0 (38)

from
$164

Private Morning Tour Lagoon 400-380 Sailing in Santorini,lunch, drink, transfer

Discover the most beautiful locations that Santorini has to offer on our beautiful Lagoon 400. Our crew will welcome you with open arms and provide …More

Santorini, Greece

5.0 (62)

Private Morning Tour Lagoon 400-380 Sailing in Santorini,lunch, drink, transfer

Discover the most beautiful locations that Santorini has to offer on our beautiful Lagoon 400. Our crew will welcome you with open arms and provide...

5 hours Hotel pickup offered Free Cancellation

5.0 (62)

from
$162

Kleftiko Full Day Sailing Cruise with Snorkeling & Lunch

Discover the beautiful coast line of Milos and its fantastic and unapproachable beaches with our sailing yachts and find an exciting and alternative way in …More

Milos, Greece

4.9 (133)

Kleftiko Full Day Sailing Cruise with Snorkeling & Lunch

Discover the beautiful coast line of Milos and its fantastic and unapproachable beaches with our sailing yachts and find an exciting and alternative way in...

9 to 10 hours Free Cancellation

4.9 (133)

from
$160

Santorini Sailing for Cruise Guests A Volcano and Beach Tour

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a …More

Santorini, Greece

5.0 (2)

Santorini Sailing for Cruise Guests A Volcano and Beach Tour

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a...

6 hours Free Cancellation

5.0 (2)

from
$160

Mykonos Catamaran Sunset Semi private Cruise 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

5.0 (19)

Mykonos Catamaran Sunset Semi private Cruise 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 Free Cancellation

5.0 (19)

from
$159

Santorini Half Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport

Enjoy unique views of Santorini from the sea during this 5 hour morning or sunset cruise. Starting from the port of Vlychada, see the Vlychada …More

Santorini, Greece

4.9 (87)

Santorini Half Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport

Enjoy unique views of Santorini from the sea during this 5 hour morning or sunset cruise. Starting from the port of Vlychada, see the Vlychada...

5 hours Hotel pickup offered Free Cancellation

4.9 (87)

from
$159

Milos oneiro-kleftiko sailing experience with local guide

Tour with a sailing boat like a semi private trip with a small group of people. Our local skipper offers a slow close-up approach of …More

Milos, Greece

5.0 (441)

Milos oneiro-kleftiko sailing experience with local guide

Tour with a sailing boat like a semi private trip with a small group of people. Our local skipper offers a slow close-up approach of...

7 hours Free Cancellation

5.0 (441)

from
$159

All inclusive Delos & Rhenia Islands tour (free transportation)

What makes our product unique is the contact with sea & sun. Sailing away with Nadia K, you will have the opportunity to experience new …More

Mykonos, Greece

4.9 (239)

All inclusive Delos & Rhenia Islands tour (free transportation)

What makes our product unique is the contact with sea & sun. Sailing away with Nadia K, you will have the opportunity to experience new...

6 hours Hotel pickup offered Free Cancellation

4.9 (239)

from
$157

Small group,swim in Rhenia,watch the sunset fm LVenice, freetrans

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice, …More

Mykonos, Greece

4.6 (28)

Small group,swim in Rhenia,watch the sunset fm LVenice, freetrans

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice,...

4 to 5 hours Hotel pickup offered Free Cancellation

4.6 (28)

from
$155

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

Half Day Sailing to Kleftiko with Lunch, Open Bar & Snorkeling

Kleftiko Boat Tour an unforgettable journey to Milos’ hidden gems, where adventure meets tranquility on the crystal clear waters of the Aegean. Embark on an …More

Milos, Greece

5.0 (306)

Half Day Sailing to Kleftiko with Lunch, Open Bar & Snorkeling

Kleftiko Boat Tour an unforgettable journey to Milos’ hidden gems, where adventure meets tranquility on the crystal clear waters of the Aegean. Embark on an...

7 hours Free Cancellation

5.0 (306)

from
$154

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 (7,655)

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 (7,655)

from
$149

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
$149

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
$149

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

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

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?