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 →

Santorini Private Luxury Yacht Sunset Cruise

A Private & Unique Sunset Experience aboard a Motor Yacht , to enjoy sightseeing, swimming, snorkeling, sunbathing and relaxing. You are going to explore the …More

Saronic Gulf Islands, Greece

5.0 (1)

Santorini Private Luxury Yacht Sunset Cruise

A Private & Unique Sunset Experience aboard a Motor Yacht , to enjoy sightseeing, swimming, snorkeling, sunbathing and relaxing. You are going to explore the...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$3,070

4h Private Cruise PAROS – PANTERONISIA – SOUTH COASTLINE OF PAROS

Relax and enjoy the beauty of Paros beaches! Our Private Day Cruise of Paros South Coast & Panteronisi Island offers you the unique opportunity to …More

Paros, Greece

5.0 (1)

4h Private Cruise PAROS – PANTERONISIA – SOUTH COASTLINE OF PAROS

Relax and enjoy the beauty of Paros beaches! Our Private Day Cruise of Paros South Coast & Panteronisi Island offers you the unique opportunity to...

4 hours Free Cancellation

5.0 (1)

from
$1,118

Half Day Catamaran Afternoon Cruise in Kleftiko

The Half day afternoon cruise will remain etched in your mind until you repeat it. Enjoy the natural beauties and the incredible variety of rocks, …More

Milos, Greece

5.0 (1)

Half Day Catamaran Afternoon Cruise in Kleftiko

The Half day afternoon cruise will remain etched in your mind until you repeat it. Enjoy the natural beauties and the incredible variety of rocks,...

6 hours Free Cancellation

5.0 (1)

from
$177

Santorini Caldera: Private Flybridge Yacht Experience

Azimut 42, or 13 meters of comfort - an amazing use of space, the quality of life aboard, enhanced by details that make all the …More

Santorini, Greece

5.0 (1)

Santorini Caldera: Private Flybridge Yacht Experience

Azimut 42, or 13 meters of comfort - an amazing use of space, the quality of life aboard, enhanced by details that make all the...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$183

Sunsets and Santorini go together like the Eiffel Tower and Paris. Come dusk, the skies over the island fill with swirls of red, gold and …More

Santorini, Greece

5.0 (1)

Santorini Sunset Cruise

Sunsets and Santorini go together like the Eiffel Tower and Paris. Come dusk, the skies over the island fill with swirls of red, gold and...

6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$87

Santorini Traditional Villages and Oia Sunset Tour

Discover Santorini’s traditional charm on a bus tour through Mesa Gonia and Pyrgos, ending in the picturesque village of Oia, famous for its spectacular sunset …More

Santorini, Greece

4.2 (6)

Santorini Traditional Villages and Oia Sunset Tour

Discover Santorini’s traditional charm on a bus tour through Mesa Gonia and Pyrgos, ending in the picturesque village of Oia, famous for its spectacular sunset...

6 to 7 hours Hotel pickup offered Free Cancellation

4.2 (6)

from
$51

Sunset Semi-Private Sea Tour Paros -Alyki port

Departure from the marina of Alyki. Relax on a wonderful semiprivate sunset cruise, swimming in secluded areas between Paros and Antiparos, such as Blue Lagoon …More

Paros, Greece

5.0 (1)

Sunset Semi-Private Sea Tour Paros -Alyki port

Departure from the marina of Alyki. Relax on a wonderful semiprivate sunset cruise, swimming in secluded areas between Paros and Antiparos, such as Blue Lagoon...

3 hours Free Cancellation

5.0 (1)

from
$74

A peaceful romantic trip with the essence of a cruise to be unforgettable. Embark on this afternoon excursion! …More

Santorini, Greece

4.3 (3)

Santorini Sunset cruise

A peaceful romantic trip with the essence of a cruise to be unforgettable. Embark on this afternoon excursion!...

5 hours Free Cancellation

4.3 (3)

from
$51

Private Boat Tour to Koufonisia & Small Cyclades

Embark on a unique cruise to discover hidden Cycladic gems. Enjoy personalized service from a local captain, authentic experiences, and create lasting memories. Feel the …More

Antiparos, Greece

5.0 (1)

Private Boat Tour to Koufonisia & Small Cyclades

Embark on a unique cruise to discover hidden Cycladic gems. Enjoy personalized service from a local captain, authentic experiences, and create lasting memories. Feel the...

7 hours Free Cancellation

5.0 (1)

from
$1,368

Shared Day Cruise to Little Venice & Agios Stefanos

Enjoy a most memorable cruise of the most popular highlights of Mykonos, Little Venice and Agios Stefanos. …More

Mykonos, Greece

5.0 (1)

Shared Day Cruise to Little Venice & Agios Stefanos

Enjoy a most memorable cruise of the most popular highlights of Mykonos, Little Venice and Agios Stefanos....

5 hours 30 minutes Free Cancellation

5.0 (1)

from
$80

A lazy cruise along the South coast ( wind protected ) of Mykonos with three stops on beautiful and unique beaches for snorkeling , lunch and fun …More

Mykonos, Greece

4.7 (3)

South Coast Cruise

A lazy cruise along the South coast ( wind protected ) of Mykonos with three stops on beautiful and unique beaches for snorkeling , lunch and fun...

8 hours Free Cancellation

4.7 (3)

from
$100

Mykonos Shore Excursion: Private Tour to Delos Island

When you arrive in port in Mykonos, head out on a private shore excursion to the island of Delos, where you'll discover its legends and …More

5.0 (1)

Mykonos Shore Excursion: Private Tour to Delos Island

When you arrive in port in Mykonos, head out on a private shore excursion to the island of Delos, where you'll discover its legends and...

4 hours

5.0 (1)

from
$238

Private Cruise: PAROS – PANTERONISIA – SOUTH COASTLINE OF PAROS

Relax and enjoy the beauty of Paros beaches! Our Private Day Cruise of Paros South Coast & Panteronisi Island offers you the unique opportunity to …More

Paros, Greece

5.0 (1)

Private Cruise: PAROS – PANTERONISIA – SOUTH COASTLINE OF PAROS

Relax and enjoy the beauty of Paros beaches! Our Private Day Cruise of Paros South Coast & Panteronisi Island offers you the unique opportunity to...

8 hours Free Cancellation

5.0 (1)

from
$1,712

5 Hour Milos to Kleftiko and Sykia Boat Cruise

Embark on a half-day cruise to explore iconic destinations like Kleftiko and Sykia Cave. Discover hidden gems such as Gerakas and Tsigrado, and admire the …More

Milos, Greece

5.0 (1)

5 Hour Milos to Kleftiko and Sykia Boat Cruise

Embark on a half-day cruise to explore iconic destinations like Kleftiko and Sykia Cave. Discover hidden gems such as Gerakas and Tsigrado, and admire the...

5 hours Free Cancellation

5.0 (1)

from
$970

Luxury cruise in Greece to the CYCLADES by sailboat with CHEF

The most beautiful Greek islands, an elegant and fast sailing boat, delicious food and wonderful sea... And you? What do you dream about for your …More

Ios, Greece

5.0 (1)

Luxury cruise in Greece to the CYCLADES by sailboat with CHEF

The most beautiful Greek islands, an elegant and fast sailing boat, delicious food and wonderful sea... And you? What do you dream about for your...

8 days

5.0 (1)

from
$1,476

EXPLORE - Tour Adventure Koufonisia & Naxos (Private max 10 Pax)

From Paros Piso Livadi Port - Exclusive Private Sailing Adventure Around the Koufonisia Archipelago and Naxos. Enjoy an exclusive sailing trip through the stunning waters …More

Paros, Greece

5.0 (1)

EXPLORE - Tour Adventure Koufonisia & Naxos (Private max 10 Pax)

From Paros Piso Livadi Port - Exclusive Private Sailing Adventure Around the Koufonisia Archipelago and Naxos. Enjoy an exclusive sailing trip through the stunning waters...

9 hours Free Cancellation

5.0 (1)

from
$1,930

Our captain’s professionalism, the presence of co-captain Dior - the cutest mini Maltese that steals the show- combined with our rib boat’s amenities offers the …More

Santorini, Greece

5.0 (1)

Private Caldera Cruise Santorini

Our captain’s professionalism, the presence of co-captain Dior - the cutest mini Maltese that steals the show- combined with our rib boat’s amenities offers the...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$1,249

5 HourS Blue Lagoon start 1530 - cliff jumping in TRIPITI

Staring from Piso Livadi port, located at the South East coast of Paros we offer a HALF DAY sailing cruise, tailored for the traveller who …More

Paros, Greece

5.0 (1)

5 HourS Blue Lagoon start 1530 - cliff jumping in TRIPITI

Staring from Piso Livadi port, located at the South East coast of Paros we offer a HALF DAY sailing cruise, tailored for the traveller who...

4 hours 45 minutes Free Cancellation

5.0 (1)

from
$126

Shared Full Day Volcano Sightseeing in Nisiros with Guide

A cruise down south of Kos Island to the volcanic island of Nissyros. A tour by bus will take you right into the heart of …More

Tinos, Greece

5.0 (1)

Shared Full Day Volcano Sightseeing in Nisiros with Guide

A cruise down south of Kos Island to the volcanic island of Nissyros. A tour by bus will take you right into the heart of...

10 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$57

Santorini Tour of Caldera & Sunset In Oia with Glass-bottom Boat

Get on our Glass Bottom Boat for a cruise, explore the volcanic islands of Santorini , walk through the narrow streets of Oia & take …More

Santorini, Greece

4.2 (5)

Santorini Tour of Caldera & Sunset In Oia with Glass-bottom Boat

Get on our Glass Bottom Boat for a cruise, explore the volcanic islands of Santorini , walk through the narrow streets of Oia & take...

9 hours Free Cancellation

4.2 (5)

from
$62

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?