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 →

Discover Nisyros and Spend A Day in Aegean Paradise

Discover the hidden gem of Nisyros, just a 40-minute journey from Kos's Kardamena. Experience the awe-inspiring Polyvotis Volcano, a natural wonder that promises an unforgettable …More

Tinos, Greece

3.8 (4)

Discover Nisyros and Spend A Day in Aegean Paradise

Discover the hidden gem of Nisyros, just a 40-minute journey from Kos's Kardamena. Experience the awe-inspiring Polyvotis Volcano, a natural wonder that promises an unforgettable...

7 hours 30 minutes Hotel pickup offered Free Cancellation

3.8 (4)

from
$47

Santorini Tour of Caldera with Glass bottom Boat

Τhis option is the most complete! allows you to visit all the islands of the Caldera. Ideal for cruise travelers, as the boat tour begins …More

Santorini, Greece

3.5 (8)

Santorini Tour of Caldera with Glass bottom Boat

Τhis option is the most complete! allows you to visit all the islands of the Caldera. Ideal for cruise travelers, as the boat tour begins...

5 hours 30 minutes Free Cancellation

3.5 (8)

from
$42

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

Private Catamaran Half Day Morning Cruise: Kleftiko

We are heading to the impressive Cape Vani and our first stop for a swim, the natural bay of Kalogries, ideal for diving from the …More

Milos, Greece

4.0 (4)

Private Catamaran Half Day Morning Cruise: Kleftiko

We are heading to the impressive Cape Vani and our first stop for a swim, the natural bay of Kalogries, ideal for diving from the...

5 hours 30 minutes

4.0 (4)

from
$225

Agios Georgios Wooden Boat, Blue Lagoon,Antiparos, Sea Caves

Enjoy a unique sea tour from Piso Livadi port, into the South parts of Paros and Antiparos such as Blue lagoon, Despotiko, Sea caves, and …More

Paros, Greece

3.8 (4)

Agios Georgios Wooden Boat, Blue Lagoon,Antiparos, Sea Caves

Enjoy a unique sea tour from Piso Livadi port, into the South parts of Paros and Antiparos such as Blue lagoon, Despotiko, Sea caves, and...

7 hours 30 minutes Free Cancellation

3.8 (4)

from
$177

After a 10-minute trip, the boat arrives at the port of Erinia which is the name of the small bay of the volcano. The ship …More

Santorini, Greece

3.5 (2)

Santorini Volcano & Hot Springs Tour

After a 10-minute trip, the boat arrives at the port of Erinia which is the name of the small bay of the volcano. The ship...

3 hours Free Cancellation

3.5 (2)

from
$52

3 Hours Private Sunset Tour in Greece with Free Drinks & Snacks

Close your eyes and create an image of setting sail towards the horizon with a glass of wine on hand, watching the sun dipping into …More

Mykonos, Greece

3.0 (2)

3 Hours Private Sunset Tour in Greece with Free Drinks & Snacks

Close your eyes and create an image of setting sail towards the horizon with a glass of wine on hand, watching the sun dipping into...

3 hours Hotel pickup offered Free Cancellation

3.0 (2)

from
$86

Full Day Private Boat Cruise in Small Cyclades

Embark on a daily cruise from the enchanting Paros Island to the hidden gems of the Small Cyclades, an archipelago that promises a serene escape …More

Mykonos, Greece

Full Day Private Boat Cruise in Small Cyclades

Embark on a daily cruise from the enchanting Paros Island to the hidden gems of the Small Cyclades, an archipelago that promises a serene escape...

6 to 8 hours Hotel pickup offered

from
$2,625

Embark on an enchanting journey where the Aegean Sea unveils its mesmerizing beauty as the sun gracefully descends. As you step aboard the luxurious cruise …More

Mykonos, Greece

Sunset Cruise

Embark on an enchanting journey where the Aegean Sea unveils its mesmerizing beauty as the sun gracefully descends. As you step aboard the luxurious cruise...

3 hours Hotel pickup offered

from
$1,027

Private Boat Cruise Tour in Milos and Polyaigos

Dive into the crystal-clear waters for a refreshing swim or bask in the sun on the untouched shores. The island’s rugged landscapes and serene atmosphere …More

Mykonos, Greece

Private Boat Cruise Tour in Milos and Polyaigos

Dive into the crystal-clear waters for a refreshing swim or bask in the sun on the untouched shores. The island’s rugged landscapes and serene atmosphere...

6 to 8 hours Hotel pickup offered

from
$3,281

Private Bachelor Or Honeymoon Cruise In Mykonos Island

Are you looking for a romantic getaway or planning your pre wedding/bachelor party? This cruise is for you! Take your friends or family and enjoy …More

Mykonos, Greece

Private Bachelor Or Honeymoon Cruise In Mykonos Island

Are you looking for a romantic getaway or planning your pre wedding/bachelor party? This cruise is for you! Take your friends or family and enjoy...

5 hours Hotel pickup offered

from
$2,446

Half Day Private Cruise Mykonos to Delos and Rhenia

Enjoy a half day private cruise with your family or friends to Delos and Rhenia. Departing from Ornos dock, we will sail to the famous …More

Mykonos, Greece

Half Day Private Cruise Mykonos to Delos and Rhenia

Enjoy a half day private cruise with your family or friends to Delos and Rhenia. Departing from Ornos dock, we will sail to the famous...

5 hours Hotel pickup offered

from
$2,218

5 Hour Private Cruise Mykonos - South Coast - Glamorous Side

Enjoy a private cruise with your family or friends through the South coast of Mykonos island. In this cruise you will have the chance to …More

Mykonos, Greece

5 Hour Private Cruise Mykonos - South Coast - Glamorous Side

Enjoy a private cruise with your family or friends through the South coast of Mykonos island. In this cruise you will have the chance to...

5 hours Hotel pickup offered

from
$2,441

Experience a Full Day schedule of your preference on a luxury Motoryacht of at least 62ft, visiting nearby beaches and islands of Mykonos and meet …More

Mykonos, Greece

Private Yacht in Mykonos

Experience a Full Day schedule of your preference on a luxury Motoryacht of at least 62ft, visiting nearby beaches and islands of Mykonos and meet...

8 hours Hotel pickup offered

from
$8,532

Private Cruise from Mykonos to Heraklia via Koufonisia & Schinousa

ROUTE The cruise starts from Ammoudi port at 11:00 and cruises below Caldera. • First stop: Thirasia island for photos. Cruise past Aspronisi, Ancient light …More

Mykonos, Greece

Private Cruise from Mykonos to Heraklia via Koufonisia & Schinousa

ROUTE The cruise starts from Ammoudi port at 11:00 and cruises below Caldera. • First stop: Thirasia island for photos. Cruise past Aspronisi, Ancient light...

7 hours

from
$1,850

Private Cruise from Mykonos to Rhenia via Delos

After a short boat trip we arrive in Delos island. Delos is one of the most beautiful Unesco's World Heritage archeological sites in the world. …More

Mykonos, Greece

Private Cruise from Mykonos to Rhenia via Delos

After a short boat trip we arrive in Delos island. Delos is one of the most beautiful Unesco's World Heritage archeological sites in the world....

3 hours

from
$1,593

Private Cruise from Mykonos to Dragonisi via the south coastline

After a short boat trip we arrive in Delos island. Delos is one of the most beautiful Unesco's World Heritage archeological sites in the world. …More

Mykonos, Greece

Private Cruise from Mykonos to Dragonisi via the south coastline

After a short boat trip we arrive in Delos island. Delos is one of the most beautiful Unesco's World Heritage archeological sites in the world....

3 hours

from
$1,593

Private Sunset Half Day Tour from Santorini to Volcano & Aspronisi

Welcome on board! With this tour we are ready to explore the hidden beauty of Santorini. Visiting the most spectacular beaches, explore the blue green …More

Santorini, Greece

Private Sunset Half Day Tour from Santorini to Volcano & Aspronisi

Welcome on board! With this tour we are ready to explore the hidden beauty of Santorini. Visiting the most spectacular beaches, explore the blue green...

5 hours Hotel pickup offered

from
$2,844

Private Day Yachttrip from Santorini to Thirasia via Red beach & Hot Springs

The cruise starts from the harbor of Vlychada at 10:00 in the morning: • First stop is at the Red Beach • Second stop is …More

Santorini, Greece

Private Day Yachttrip from Santorini to Thirasia via Red beach & Hot Springs

The cruise starts from the harbor of Vlychada at 10:00 in the morning: • First stop is at the Red Beach • Second stop is...

5 hours

from
$3,754

Day Private Cruise to Caldera & Hot Springs via White&Black beach from Santorini

Make your visit a truly memorable one by sailing with our 9 meter speedboat with a very experienced crew. Let our professional crew of the …More

Santorini, Greece

Day Private Cruise to Caldera & Hot Springs via White&Black beach from Santorini

Make your visit a truly memorable one by sailing with our 9 meter speedboat with a very experienced crew. Let our professional crew of the...

5 hours

from
$2,787

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?