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 →

Private Cruise with Galatea(Paros,Antiparos,Despotiko,Bluelagoon)

Galatea is a beautiful Turkish schooner, the only one on the island of Paros, 19m long x 5.5m wide, with elegant shapes and large living …More

Paros, Greece

5.0 (9)

Private Cruise with Galatea(Paros,Antiparos,Despotiko,Bluelagoon)

Galatea is a beautiful Turkish schooner, the only one on the island of Paros, 19m long x 5.5m wide, with elegant shapes and large living...

4 to 9 hours

5.0 (9)

from
$2,526

Private Cruise: MYKONOS – ANTIPAROS – DESPOTIKO - PANTERONISIA

A day full of dazzling natural beauty and history! Join our private day cruise from Paros to Antiparos, Despotiko, Panteronisi and explore 3 majestic islands. …More

Mykonos, Greece

5.0 (7)

Private Cruise: MYKONOS – ANTIPAROS – DESPOTIKO - PANTERONISIA

A day full of dazzling natural beauty and history! Join our private day cruise from Paros to Antiparos, Despotiko, Panteronisi and explore 3 majestic islands....

8 hours Free Cancellation

5.0 (7)

from
$3,081

Full Day Boat Tour Around Milos and Poliegos

Every side of the island has complete different things to offer you! There are caves and stories about pirates . There are huge piles of …More

Milos, Greece

4.8 (8)

Full Day Boat Tour Around Milos and Poliegos

Every side of the island has complete different things to offer you! There are caves and stories about pirates . There are huge piles of...

10 hours Free Cancellation

4.8 (8)

from
$182

Half day Private Sailing cruise in Santorini island up to 6 pax

Enjoy the cruise like a real sailor and experience moving with the force of the wind! Maria our captain will stand our, together with our …More

Santorini, Greece

5.0 (6)

Half day Private Sailing cruise in Santorini island up to 6 pax

Enjoy the cruise like a real sailor and experience moving with the force of the wind! Maria our captain will stand our, together with our...

5 hours Free Cancellation

5.0 (6)

from
$1,033

Private Cruise with Handmade Antique Boat around Mykonos-Full Day

Sail as local! With a traditional handmade Kaiki-the rare type of varkalas. We are a family business and we will introduce you to the authentic …More

Mykonos, Greece

5.0 (9)

Private Cruise with Handmade Antique Boat around Mykonos-Full Day

Sail as local! With a traditional handmade Kaiki-the rare type of varkalas. We are a family business and we will introduce you to the authentic...

6 hours Free Cancellation

5.0 (9)

from
$1,010

Private Milos Tour "Pirates’ Hideout"- Luxury Boat Rental

Begin this tour by visiting Triades, a collection of three fine-grained yellow sandy beaches with crystal clear shallow blue waters. Then, take a dip in …More

Milos, Greece

5.0 (6)

Private Milos Tour "Pirates’ Hideout"- Luxury Boat Rental

Begin this tour by visiting Triades, a collection of three fine-grained yellow sandy beaches with crystal clear shallow blue waters. Then, take a dip in...

5 hours Free Cancellation

5.0 (6)

from
$1,107

Full Day Tour to Kleftiko, Firlingos and Poliegos Catamaran

Sailing across the coastline, we will pass by the traditional fishing villages of Skinopi, Klima with the colorful little houses – called “Sirmata”- built by …More

Milos, Greece

5.0 (7)

Full Day Tour to Kleftiko, Firlingos and Poliegos Catamaran

Sailing across the coastline, we will pass by the traditional fishing villages of Skinopi, Klima with the colorful little houses – called “Sirmata”- built by...

10 hours Free Cancellation

5.0 (7)

from
$223

Private Half Day Morning Cruise of Milos and Kleftiko

This private sailing cruise offers a premium, all-inclusive experience on a modern sailing yacht exclusively for you. With a dedicated captain and hostess on board, …More

Milos, Greece

5.0 (8)

Private Half Day Morning Cruise of Milos and Kleftiko

This private sailing cruise offers a premium, all-inclusive experience on a modern sailing yacht exclusively for you. With a dedicated captain and hostess on board,...

6 hours 30 minutes Free Cancellation

5.0 (8)

from
$1,706

Private Cruise All Around Of Milos & Sunset to Klima Village

“Our private ‘All Around Milos & Sunset’ cruise is the perfect way to explore the island at your own pace. With your own captain and …More

Milos, Greece

5.0 (6)

Private Cruise All Around Of Milos & Sunset to Klima Village

“Our private ‘All Around Milos & Sunset’ cruise is the perfect way to explore the island at your own pace. With your own captain and...

12 hours Free Cancellation

5.0 (6)

from
$1,718

2-Hour Mykonos Private Sea Safari and Snorkeling on a Powerboat

Experience a stunning boat tour to the southern tip of Mykonos Island. Discover its unique coves and virgin beaches with a full set of snorkeling …More

Mykonos, Greece

4.6 (10)

2-Hour Mykonos Private Sea Safari and Snorkeling on a Powerboat

Experience a stunning boat tour to the southern tip of Mykonos Island. Discover its unique coves and virgin beaches with a full set of snorkeling...

2 hours Free Cancellation

4.6 (10)

from
$1,084

Santorini Private Tour Half-Day Sailing Platinum Catamaran Cruise

This tour provides a complete experience of Santorini! You can swim in unique and otherwise impassable locations, enjoying the most wonderful of vistas while sailing …More

Santorini, Greece

4.9 (9)

Santorini Private Tour Half-Day Sailing Platinum Catamaran Cruise

This tour provides a complete experience of Santorini! You can swim in unique and otherwise impassable locations, enjoying the most wonderful of vistas while sailing...

5 hours Free Cancellation

4.9 (9)

from
$236

Morning Half Day Shared Speed Boat Trip to Sikia and Kleftiko

Welcome on board! We cruise together for a half-day trip across the coast of Milos! We choose some of the most beautiful spots to swim, …More

Milos, Greece

5.0 (7)

Morning Half Day Shared Speed Boat Trip to Sikia and Kleftiko

Welcome on board! We cruise together for a half-day trip across the coast of Milos! We choose some of the most beautiful spots to swim,...

4 hours Free Cancellation

5.0 (7)

from
$271

Small-Group Guided Hiking Tour in Andros with picnic on the beach

Let us take you out of your comfort zone and fall in love with the thrill of discovering and discovering yourself. On this walking tour, …More

Andros, Greece

5.0 (7)

Small-Group Guided Hiking Tour in Andros with picnic on the beach

Let us take you out of your comfort zone and fall in love with the thrill of discovering and discovering yourself. On this walking tour,...

4 to 6 hours Hotel pickup offered Free Cancellation

5.0 (7)

from
$108

Full Day Boat Tour to Kleftiko & Sykia Cave

Our special trip is a full day tour gift to the soul, as you have the chance to witness virial historical monuments, by the sea, …More

Milos, Greece

5.0 (6)

Full Day Boat Tour to Kleftiko & Sykia Cave

Our special trip is a full day tour gift to the soul, as you have the chance to witness virial historical monuments, by the sea,...

8 hours Free Cancellation

5.0 (6)

from
$182

5 Hour Private Day or Sunset Cruise in Large & Majestic Catamaran

Step aboard this large and majestic catamaran (equipped with all the amenities of a 5 star floating hotel including AC) and enjoy a comfortable and …More

Mykonos, Greece

5.0 (6)

5 Hour Private Day or Sunset Cruise in Large & Majestic Catamaran

Step aboard this large and majestic catamaran (equipped with all the amenities of a 5 star floating hotel including AC) and enjoy a comfortable and...

5 hours Free Cancellation

5.0 (6)

from
$223

Luxury Private Boat Tour in Ios with the Saxdor 320

A unique experience exclusively for you and your loved ones. Discover our island and swim in some of the bluest waters of the Aegean. A …More

Ios, Greece

5.0 (5)

Luxury Private Boat Tour in Ios with the Saxdor 320

A unique experience exclusively for you and your loved ones. Discover our island and swim in some of the bluest waters of the Aegean. A...

4 to 8 hours Free Cancellation

5.0 (5)

from
$171

Guided Walking Tour Mykonos, Little Venice, Windmills, Beaches

Book this private shore excursion in Mykonos as a great opportunity to explore the "Island of Winds". You will see the lovely churches, the tiny …More

Mykonos, Greece

5.0 (6)

Guided Walking Tour Mykonos, Little Venice, Windmills, Beaches

Book this private shore excursion in Mykonos as a great opportunity to explore the "Island of Winds". You will see the lovely churches, the tiny...

4 hours Hotel pickup offered

5.0 (6)

from
$163

Mykonos Catamaran Private Delos Rhenia cruise

Indulge in this daily cruise to Delos and Rhenia islands, which lets you bask in the warm Mykonian sun, enjoying the summer breeze as you …More

Mykonos, Greece

4.9 (7)

Mykonos Catamaran Private Delos Rhenia cruise

Indulge in this daily cruise to Delos and Rhenia islands, which lets you bask in the warm Mykonian sun, enjoying the summer breeze as you...

6 hours Free Cancellation

4.9 (7)

from
$2,054

Luxury Private Power Catamaran Tour in Santorini

This is not a cookie-cutter approach to cruise sailing! Make your own schedule with us and choose the places you wish to see! Lucky 8 …More

Santorini, Greece

5.0 (7)

Luxury Private Power Catamaran Tour in Santorini

This is not a cookie-cutter approach to cruise sailing! Make your own schedule with us and choose the places you wish to see! Lucky 8...

3 hours

5.0 (7)

from
$1,837

Mykonos tour beaches small group of up to 10 passengers best trip

The boarding time on boat is at 10:00 at Kalafatis beach, the crew will offer you a welcome drink and show you the route, the …More

Mykonos, Greece

5.0 (9)

Mykonos tour beaches small group of up to 10 passengers best trip

The boarding time on boat is at 10:00 at Kalafatis beach, the crew will offer you a welcome drink and show you the route, the...

5 hours Hotel pickup offered Free Cancellation

5.0 (9)

from
$182

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?

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

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?