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 →

Cruise with us in sophisticated chic style and discover the gorgeous nearby island of Rhenia or the famous Mykonian southern coast. Our luxurious, brand new …More

Mykonos, Greece

5.0 (21)

Private 5-Hour Cruise on Brand-New 2023 Motor Yacht in Mykonos (Voreus)

Cruise with us in sophisticated chic style and discover the gorgeous nearby island of Rhenia or the famous Mykonian southern coast. Our luxurious, brand new...

5 hours Hotel pickup offered Free Cancellation

5.0 (21)

from
$976

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
$176

Paros-Antiparos Private Cruise on a Luxurious Saxdor 320

Are you in Paros for a long holiday or just spending a few days? Why not take the most of it? Book a ride and …More

Paros, Greece

4.9 (20)

Paros-Antiparos Private Cruise on a Luxurious Saxdor 320

Are you in Paros for a long holiday or just spending a few days? Why not take the most of it? Book a ride and...

7 hours Free Cancellation

4.9 (20)

from
$1,894

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

Mykonos Catamaran Delos Rhenia Cruise with Lunch and Transfer

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

5.0 (33)

Mykonos Catamaran Delos Rhenia Cruise with Lunch and Transfer

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 Hotel pickup offered Free Cancellation

5.0 (33)

from
$205

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

Island Hopping: Santorini Catamaran Charter Cruise with a skipper

Design your own trip and explore the Aegean! Feel free to craft your own personalized sailing route. We are ready to make it happen. Set …More

Paros, Greece

4.9 (123)

Island Hopping: Santorini Catamaran Charter Cruise with a skipper

Design your own trip and explore the Aegean! Feel free to craft your own personalized sailing route. We are ready to make it happen. Set...

7 days

4.9 (123)

from
$8,450

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
$102

Private Boat Tour to Antiparos and Blue Lagoon

Embark on an unforgettable adventure exploring the hidden gems of the Cyclades with our exclusive boat tour departing from Naxos or Paros. Our first stop …More

Naxos, Greece

4.9 (33)

Private Boat Tour to Antiparos and Blue Lagoon

Embark on an unforgettable adventure exploring the hidden gems of the Cyclades with our exclusive boat tour departing from Naxos or Paros. Our first stop...

6 to 8 hours Free Cancellation

4.9 (33)

from
$1,311

Mykonos Catamaran Sunset Cruise with Meal, Drinks & Transfer

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches …More

Mykonos, Greece

4.9 (127)

Mykonos Catamaran Sunset Cruise with Meal, Drinks & Transfer

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches...

4 hours Hotel pickup offered Free Cancellation

4.9 (127)

from
$142

Antiparos Odyssey: Caves, Blue Lagoon & Coastal Charms|Boat Tour

Explore the charming streets of Antiparos, a serene destination favoured by celebrities. Marvel at the stunning Cave of Trypiti, a natural wonder, take photos and …More

Antiparos, Greece

5.0 (24)

Antiparos Odyssey: Caves, Blue Lagoon & Coastal Charms|Boat Tour

Explore the charming streets of Antiparos, a serene destination favoured by celebrities. Marvel at the stunning Cave of Trypiti, a natural wonder, take photos and...

4 hours Free Cancellation

5.0 (24)

from
$1,140

Private sailing cruise to Delos & Rhenia with Lunch & Transfer

Our first stop is an hour away, the renowned Big Delos island. While there, you will have the opportunity to visit one of the most …More

Mykonos, Greece

5.0 (12)

Private sailing cruise to Delos & Rhenia with Lunch & Transfer

Our first stop is an hour away, the renowned Big Delos island. While there, you will have the opportunity to visit one of the most...

6 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$2,227

Santorini: Private Catamaran Cruise with Fresh Fish BBQ & Drinks

The Private Sailing Cruise by Renieris Santorini Sailing Center starting from Vlychada marina is a great opportunity to customize your own cruise and enjoy the …More

Santorini, Greece

5.0 (19)

Santorini: Private Catamaran Cruise with Fresh Fish BBQ & Drinks

The Private Sailing Cruise by Renieris Santorini Sailing Center starting from Vlychada marina is a great opportunity to customize your own cruise and enjoy the...

5 hours Hotel pickup offered Free Cancellation

5.0 (19)

from
$179

Santorini Caldera Morning Cruise With King Thiras Boat

What makes this tour unique is the opportunity to visit the main landmarks of Santorini in one day, enjoying amazing views and sceneries. …More

Santorini, Greece

4.3 (36)

Santorini Caldera Morning Cruise With King Thiras Boat

What makes this tour unique is the opportunity to visit the main landmarks of Santorini in one day, enjoying amazing views and sceneries....

7 hours Free Cancellation

4.3 (36)

from
$58

We know the whole island like the palm of our hand. We can take you to dramatic sea caves and beaches so secluded even the …More

Milos, Greece

5.0 (15)

Milos Island Full day Private Tour

We know the whole island like the palm of our hand. We can take you to dramatic sea caves and beaches so secluded even the...

8 to 9 hours Free Cancellation

5.0 (15)

from
$2,612

Santorini Caldera: Private Cruise with Speed Boat & Open Bar

Starting the tour from the marina of Vlychada, our first stop will be the volcanic Red Beach where for half an hour you will enjoy …More

Santorini, Greece

5.0 (11)

Santorini Caldera: Private Cruise with Speed Boat & Open Bar

Starting the tour from the marina of Vlychada, our first stop will be the volcanic Red Beach where for half an hour you will enjoy...

4 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$159

Motor Yacht (2026)Luxury Private Cruise Around Santorini

Enjoy a fully private experience on the luxury motor yacht Diamond, offering speed, comfort and flexibility to explore more of Santorini in less time. Unlike …More

Santorini, Greece

5.0 (12)

Motor Yacht (2026)Luxury Private Cruise Around Santorini

Enjoy a fully private experience on the luxury motor yacht Diamond, offering speed, comfort and flexibility to explore more of Santorini in less time. Unlike...

5 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$154

Small group,swim in Rhenia,watch the sunset fm LVenice, freetrans

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice, …More

Mykonos, Greece

4.6 (28)

Small group,swim in Rhenia,watch the sunset fm LVenice, freetrans

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice,...

4 to 5 hours Hotel pickup offered Free Cancellation

4.6 (28)

from
$155

All inclusive Private Cruise: Delos &Rhenia island

A full day of fun, culture and culinary discovery. Spend a perfect day out on the sea combining a relaxing sailing cruise, swimming and sunbathing …More

Mykonos, Greece

5.0 (13)

All inclusive Private Cruise: Delos &Rhenia island

A full day of fun, culture and culinary discovery. Spend a perfect day out on the sea combining a relaxing sailing cruise, swimming and sunbathing...

6 hours Free Cancellation

5.0 (13)

from
$69

Private Sunset Cruise to Klima with snacks and drinks

With the stunning backdrop of Milos Island, the tour offers the opportunity to witness a breathtaking sunset from the comfort of the luxurious Saxdor 32GTO. …More

Milos, Greece

5.0 (16)

Private Sunset Cruise to Klima with snacks and drinks

With the stunning backdrop of Milos Island, the tour offers the opportunity to witness a breathtaking sunset from the comfort of the luxurious Saxdor 32GTO....

2 hours Free Cancellation

5.0 (16)

from
$68

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?