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

Private Full Day Tour in South Paros Caves Despotiko

We sail from Pisso Livadi to the southwest by 09:30, hoisting our sails and adjusting our course according to the prevailing winds we enjoy a …More

Paros, Greece

5.0 (32)

Private Full Day Tour in South Paros Caves Despotiko

We sail from Pisso Livadi to the southwest by 09:30, hoisting our sails and adjusting our course according to the prevailing winds we enjoy a...

8 hours Free Cancellation

5.0 (32)

from
$367

Milos Sunset Catamaran Cruise to Kleftiko Bay with Meal & Drinks

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge, …More

Milos, Greece

5.0 (32)

Milos Sunset Catamaran Cruise to Kleftiko Bay with Meal & Drinks

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge,...

5 hours 30 minutes Free Cancellation

5.0 (32)

from
$177

Our cruise starts with a delicious breakfast enjoyed on board while heading towards our first destination, Panteronisia / Blue Lagoon. Once there, we will be surrounded …More

Antiparos, Greece

5.0 (31)

Glaraki Private Day Cruise

Our cruise starts with a delicious breakfast enjoyed on board while heading towards our first destination, Panteronisia / Blue Lagoon. Once there, we will be surrounded...

6 hours 45 minutes Free Cancellation

5.0 (31)

from
$1,837

Private Full One-Day Tour Naxos & Heraklia SY AGERAS

Words, pictures or videos are not enough to describe the experience onboard the Yin Yang. From the moment you will first see the yacht until …More

Paros, Greece

5.0 (29)

Private Full One-Day Tour Naxos & Heraklia SY AGERAS

Words, pictures or videos are not enough to describe the experience onboard the Yin Yang. From the moment you will first see the yacht until...

8 hours Free Cancellation

5.0 (29)

from
$365

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

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
$103

Milos Luxury Catamaran Cruise to Kleftiko Bay with Lunch

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge, …More

Milos, Greece

5.0 (22)

Milos Luxury Catamaran Cruise to Kleftiko Bay with Lunch

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge,...

5 hours 30 minutes Free Cancellation

5.0 (22)

from
$178

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

All inclusive cruise Sailing Cruise to Delos&Rhenia beaches

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

4.8 (22)

All inclusive cruise Sailing Cruise to Delos&Rhenia beaches

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...

5 hours 30 minutes Free Cancellation

4.8 (22)

from
$121

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

Milos Full-Day Premium Catamaran Cruise Kleftiko and Polyegos

Experience the magic of Milos on a luxury catamaran cruise designed for total comfort and adventure. Your journey begins at Adamantas, sailing first to the …More

Milos, Greece

5.0 (20)

Milos Full-Day Premium Catamaran Cruise Kleftiko and Polyegos

Experience the magic of Milos on a luxury catamaran cruise designed for total comfort and adventure. Your journey begins at Adamantas, sailing first to the...

9 hours Free Cancellation

5.0 (20)

from
$218

Private full day cruise to Antiparos with Paros Sail

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

Paros, Greece

5.0 (20)

Private full day cruise to Antiparos with Paros Sail

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

7 hours Free Cancellation

5.0 (20)

from
$2,454

Sailsational Luxury Santorini Catamaran Sunset Cruise with Dinner

The limited number of participants makes this catamaran sailing experience unique and different. At most, 12-20 guests take place on this catamaran sailing tour. It …More

Santorini, Greece

4.8 (19)

Sailsational Luxury Santorini Catamaran Sunset Cruise with Dinner

The limited number of participants makes this catamaran sailing experience unique and different. At most, 12-20 guests take place on this catamaran sailing tour. It...

5 to 6 hours Hotel pickup offered Free Cancellation

4.8 (19)

from
$218

Visit Volcano & Hot Springs by joining our most popular & low cost tour. An experience you don't want to miss! ideal for cruise travelers, …More

Santorini, Greece

4.8 (18)

Santorini Volcano Hot Springs

Visit Volcano & Hot Springs by joining our most popular & low cost tour. An experience you don't want to miss! ideal for cruise travelers,...

3 hours Free Cancellation

4.8 (18)

from
$34

Santorini: Caldera Private Sailing Boat Cruise with Beneteau Oceanis 46.1

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number …More

Santorini, Greece

5.0 (17)

Santorini: Caldera Private Sailing Boat Cruise with Beneteau Oceanis 46.1

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number...

5 hours Hotel pickup offered Free Cancellation

5.0 (17)

from
$183

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

Enjoy unique views of Santorini from the sea during this 7 hour daycruise, starting from the port of Vlychada. Passing from the Red Beach you …More

Santorini, Greece

4.9 (16)

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

Enjoy unique views of Santorini from the sea during this 7 hour daycruise, starting from the port of Vlychada. Passing from the Red Beach you...

7 hours Hotel pickup offered Free Cancellation

4.9 (16)

from
$262

Full Day Santorini Catamaran Private Cruise with meal and transfer

Booking a Private Catamaran Tour in Santorini is a dream come true! We offer daily cruises to Santorini’s beautiful sights. The best way to spend …More

Santorini, Greece

5.0 (16)

Full Day Santorini Catamaran Private Cruise with meal and transfer

Booking a Private Catamaran Tour in Santorini is a dream come true! We offer daily cruises to Santorini’s beautiful sights. The best way to spend...

7 hours Hotel pickup offered

5.0 (16)

from
$2,526

Mykonos Catamaran Cruise with Meal Drinks and Sup

Go on a half-day cruise in the Aegean Sea. Select your preferred departure time morning or afternoon and sail to the mythical Delos and Rhenia …More

Mykonos, Greece

4.9 (14)

Mykonos Catamaran Cruise with Meal Drinks and Sup

Go on a half-day cruise in the Aegean Sea. Select your preferred departure time morning or afternoon and sail to the mythical Delos and Rhenia...

5 hours Free Cancellation

4.9 (14)

from
$1,370

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?