Top Cyclades Islands Cruises, Sailing & Water Tours

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 →

Caldera Cruise with Swim Stops, BBQ on board and drinks!

Set out on a unique sailing adventure. The cruise takes you to the emblematic Caldera coastline, by the Black Rock of the Indian and the …More

Santorini, Greece

5.0 (27)

Caldera Cruise with Swim Stops, BBQ on board and drinks!

Set out on a unique sailing adventure. The cruise takes you to the emblematic Caldera coastline, by the Black Rock of the Indian and the...

5 hours Hotel pickup offered Free Cancellation

5.0 (27)

from
$148

Private all included yacht Tour in Santorini

"Step aboard and join the captivating journey led by the esteemed Captain George, a true son of the enchanting Santorinian Sea. Raised amidst the seafaring …More

Santorini, Greece

4.9 (38)

Private all included yacht Tour in Santorini

"Step aboard and join the captivating journey led by the esteemed Captain George, a true son of the enchanting Santorinian Sea. Raised amidst the seafaring...

3 to 5 hours Hotel pickup offered Free Cancellation

4.9 (38)

from
$292

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

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

"The best value-for-money excursion cruise in Santorini" Set sail from Ammoudi Port cruising along the coastline and visit the two most iconic sights of the …More

Santorini, Greece

4.9 (35)

Caldera Private Cruise & Volcano Hike

"The best value-for-money excursion cruise in Santorini" Set sail from Ammoudi Port cruising along the coastline and visit the two most iconic sights of the...

3 hours Free Cancellation

4.9 (35)

from
$131

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

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: Private Catamaran Cruise to Volcano with BBQ & Drinks

Experience Santorini like never before on your exclusive private catamaran cruise, fully tailored to your preferences. Swim in warm volcanic waters, snorkel in crystal-clear seas, …More

Santorini, Greece

5.0 (29)

Santorini: Private Catamaran Cruise to Volcano with BBQ & Drinks

Experience Santorini like never before on your exclusive private catamaran cruise, fully tailored to your preferences. Swim in warm volcanic waters, snorkel in crystal-clear seas,...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (29)

from
$162

Shared Catamaran Half Day Cruise in Santorini

The unique moments to be shared only with your friends or family, see the south part of Santorini (Red & White beach, Mesa Pigadia, Black …More

Santorini, Greece

4.9 (32)

Shared Catamaran Half Day Cruise in Santorini

The unique moments to be shared only with your friends or family, see the south part of Santorini (Red & White beach, Mesa Pigadia, Black...

5 hours Hotel pickup offered Free Cancellation

4.9 (32)

from
$148

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

Τhis trip is mainly aimed at visitors who don't have much time to spare, ideal for cruise travelers, as the boat tour begins at the …More

Santorini, Greece

4.3 (36)

Santorini - Volcano and Hot springs

Τhis trip is mainly aimed at visitors who don't have much time to spare, ideal for cruise travelers, as the boat tour begins at the...

3 hours Free Cancellation

4.3 (36)

from
$34

Majestic Catamaran Caldera Cruise with Snacks, Meal & Drinks

The Majestic Day or Sunset Cruise is operated by our newest catamarans which offering luxury setup with plenty of space. You'll set off from Ammoudi …More

Santorini, Greece

4.8 (23)

Majestic Catamaran Caldera Cruise with Snacks, Meal & Drinks

The Majestic Day or Sunset Cruise is operated by our newest catamarans which offering luxury setup with plenty of space. You'll set off from Ammoudi...

4 hours 30 minutes Hotel pickup offered Free Cancellation

4.8 (23)

from
$153

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

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

Small Group Kaiki Cruise & Greek Gastronomy Experience

Step aboard Agia Kali, a restored wooden kaiki, for a semi-private cruise limited to 14 guests. Discover hidden Cycladic coves, swim in crystal-clear waters, and …More

Paros, Greece

5.0 (145)

Small Group Kaiki Cruise & Greek Gastronomy Experience

Step aboard Agia Kali, a restored wooden kaiki, for a semi-private cruise limited to 14 guests. Discover hidden Cycladic coves, swim in crystal-clear waters, and...

6 hours 30 minutes Free Cancellation

5.0 (145)

from
$210

Full Day Sailboat Private Kleftiko & Blue Lagoon with Lunch

On 9hrs tour, you will discover amazing caves that can’t be reached by land accompanied by our captain.Swim in crystal clear waters all day while …More

Milos, Greece

5.0 (26)

Full Day Sailboat Private Kleftiko & Blue Lagoon with Lunch

On 9hrs tour, you will discover amazing caves that can’t be reached by land accompanied by our captain.Swim in crystal clear waters all day while...

9 hours Free Cancellation

5.0 (26)

from
$2,287

Mykonos along with Delos, Rhenia and some other rocky islets form a single island complex. Visiting these islets is a "must" for someone discovering Mykonos. …More

Mykonos, Greece

5.0 (33)

3 hour private cruise: DELOS - RHENIA

Mykonos along with Delos, Rhenia and some other rocky islets form a single island complex. Visiting these islets is a "must" for someone discovering Mykonos....

3 hours Free Cancellation

5.0 (33)

from
$858

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
$364

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
$366

Rent a SpeedBoat in Santorini with License or Skippered

Travel along Santorini Island and discover thirassia island and the volcano! Enjoy a stress-free motorboat rental that doesn't require a license! Perfect for groups or …More

Santorini, Greece

5.0 (21)

Rent a SpeedBoat in Santorini with License or Skippered

Travel along Santorini Island and discover thirassia island and the volcano! Enjoy a stress-free motorboat rental that doesn't require a license! Perfect for groups or...

10 hours Free Cancellation

5.0 (21)

from
$676

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 Cruises, Sailing & Water Tours?

What are the best kid-friendly options for Cyclades Islands Cruises, Sailing & Water Tours Tours?

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

View all kid-friendly Tours →

Which Cyclades Islands Cruises, Sailing & Water Tours have Instant Confirmation?

Cyclades Islands Cruises, Sailing & Water Tours with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Cyclades Islands Cruises, Sailing & Water Tours have Free Cancellation?

Cyclades Islands Cruises, Sailing & Water Tours 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 Cruises, Sailing & Water Tours have Hotel Pickup?

No problem. These Cyclades Islands Cruises, Sailing & Water Tours 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?