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 →

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

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

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

Half-Day Private Romantic Sailing Getaway to Kleftiko

The best custom sailing experience in Milos for the best price! Come on board Veronica classic yacht and sail the south coast of the island …More

Milos, Greece

5.0 (78)

Half-Day Private Romantic Sailing Getaway to Kleftiko

The best custom sailing experience in Milos for the best price! Come on board Veronica classic yacht and sail the south coast of the island...

5 hours Free Cancellation

5.0 (78)

from
$689

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

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
$115

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

Sailboat Full Day Tour in Kleftiko and Blue Lagoon with Lunch

Make this day unique, forget about any distraction while onboard. Enjoy a genuine adventure that will remain unforgettable. Take some stunning photos and videos that …More

Milos, Greece

5.0 (55)

Sailboat Full Day Tour in Kleftiko and Blue Lagoon with Lunch

Make this day unique, forget about any distraction while onboard. Enjoy a genuine adventure that will remain unforgettable. Take some stunning photos and videos that...

9 hours Free Cancellation

5.0 (55)

from
$189

Milos & Poliegos Catamaran Cruise Homemade Full menu BBQ & Drinks

Experience a luxury full-day cruise aboard the new catamaran Lagoon 46 “Naya II”, where elegance meets comfort and have a special day by exploring the …More

Milos, Greece

5.0 (53)

Milos & Poliegos Catamaran Cruise Homemade Full menu BBQ & Drinks

Experience a luxury full-day cruise aboard the new catamaran Lagoon 46 “Naya II”, where elegance meets comfort and have a special day by exploring the...

9 to 10 hours Free Cancellation

5.0 (53)

from
$241

Santorini Caldera Private Sailing Boat Cruise

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private …More

Santorini, Greece

4.9 (53)

Santorini Caldera Private Sailing Boat Cruise

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private...

5 hours Hotel pickup offered Free Cancellation

4.9 (53)

from
$976

Explore Santorini and its volcanic wonders with Alex Private Boat

Join us on this breathtaking trip to Nea and Palea Kammeni,the lava islands in the middle of the crater. First up, we will see the …More

Santorini, Greece

5.0 (48)

Explore Santorini and its volcanic wonders with Alex Private Boat

Join us on this breathtaking trip to Nea and Palea Kammeni,the lava islands in the middle of the crater. First up, we will see the...

3 hours Free Cancellation

5.0 (48)

from
$574

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: Private Sunset Cruise with Fresh Fish BBQ & Drinks

The Sunset Private 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 (46)

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

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

6 hours Hotel pickup offered Free Cancellation

5.0 (46)

from
$209

Experience a calm and romantic trip to the amazing sites of Santorini on a charming wooden sailing boat! The peaceful atmosphere and gentle rocking of …More

Santorini, Greece

4.9 (45)

Santorini Sunset Cruise in Caldera

Experience a calm and romantic trip to the amazing sites of Santorini on a charming wooden sailing boat! The peaceful atmosphere and gentle rocking of...

5 hours Free Cancellation

4.9 (45)

from
$51

Premium Santorini Private Day Tour Elba 45, BBQ, drinks, transfer

Explore the most attractive sights and beaches in Santorini on board the Luxurious Lagoon 450, exclusively for your party. Captain and crew will make this …More

Santorini, Greece

4.9 (45)

Premium Santorini Private Day Tour Elba 45, BBQ, drinks, transfer

Explore the most attractive sights and beaches in Santorini on board the Luxurious Lagoon 450, exclusively for your party. Captain and crew will make this...

5 hours Hotel pickup offered Free Cancellation

4.9 (45)

from
$210

A Lagoon catamaran for your group only: up to 20 guests, 5 hours by day or at sunset from Vlychada Marina. Sail past Red Beach …More

Santorini, Greece

5.0 (40)

Santorini Private Catamaran Cruise

A Lagoon catamaran for your group only: up to 20 guests, 5 hours by day or at sunset from Vlychada Marina. Sail past Red Beach...

5 hours Hotel pickup offered Free Cancellation

5.0 (40)

from
$184

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 half day cruise The Blue Lagoon with Paros Sail

You came to your vacation in Paros, there is one thing you must do! Sail and swim in the Blue Lagoon with Paros Sail. You …More

Paros, Greece

5.0 (38)

Private half day cruise The Blue Lagoon with Paros Sail

You came to your vacation in Paros, there is one thing you must do! Sail and swim in the Blue Lagoon with Paros Sail. You...

3 hours 30 minutes Free Cancellation

5.0 (38)

from
$1,357

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

Private Daily Sailing Cruise to Discover the Highlights of Milos

This cruise is unique and a must when visiting Milos . It gets you to places mostly accessible only by boat and offer the comfort …More

Milos, Greece

5.0 (34)

Private Daily Sailing Cruise to Discover the Highlights of Milos

This cruise is unique and a must when visiting Milos . It gets you to places mostly accessible only by boat and offer the comfort...

8 hours Free Cancellation

5.0 (34)

from
$1,318

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?

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?