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 3 Islands Trip by Sailing boat

Enjoy the classic tour trusted by thousands of visitors to Santorini for decades. Ideal for cruise travelers, as the boat tour begins at the port …More

Santorini, Greece

4.5 (8)

Santorini 3 Islands Trip by Sailing boat

Enjoy the classic tour trusted by thousands of visitors to Santorini for decades. Ideal for cruise travelers, as the boat tour begins at the port...

5 hours 30 minutes Free Cancellation

4.5 (8)

from
$40

All Inclusive Tour to Delos and Rhenia Islands with S/Y Olga M

Leave the crowds on Mykonos behind and catch the wind with this sailing cruise to two nearby Aegean islands. Set sail from Tourlos Bay with …More

Mykonos, Greece

5.0 (3)

All Inclusive Tour to Delos and Rhenia Islands with S/Y Olga M

Leave the crowds on Mykonos behind and catch the wind with this sailing cruise to two nearby Aegean islands. Set sail from Tourlos Bay with...

6 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$137

5 Hours Santorini Private Luxury Cruise with BBQ and Drinks

We start our tours from the marina of Vlychada. We provide 2 Private options: Private Day Cruise start 10:00 - 15:00 and Private Sunset Cruise …More

Santorini, Greece

5.0 (4)

5 Hours Santorini Private Luxury Cruise with BBQ and Drinks

We start our tours from the marina of Vlychada. We provide 2 Private options: Private Day Cruise start 10:00 - 15:00 and Private Sunset Cruise...

5 hours Hotel pickup offered Free Cancellation

5.0 (4)

from
$1,148

Antiparos-Paros: Private Cruise with Speed Boat

“THE CLASSIC GETAWAY” Quaint beaches, ancient Greek artifacts…what more is there to ask for? We start the cruise to the cosmopolitan complex of Paros and …More

Santorini, Greece

5.0 (2)

Antiparos-Paros: Private Cruise with Speed Boat

“THE CLASSIC GETAWAY” Quaint beaches, ancient Greek artifacts…what more is there to ask for? We start the cruise to the cosmopolitan complex of Paros and...

10 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$378

The alternative shared Sunset Trip from Santorini to the Gems of the island

ROUTE The cruise starts from Vlychada port at 15:15. First stop: Red Beach for swimming and snorkeling Second stop: White Beach for swimming and for …More

Santorini, Greece

5.0 (1)

The alternative shared Sunset Trip from Santorini to the Gems of the island

ROUTE The cruise starts from Vlychada port at 15:15. First stop: Red Beach for swimming and snorkeling Second stop: White Beach for swimming and for...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$245

Full-Day Private Tour in Santorini by Luxury Catamaran

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

5.0 (2)

Full-Day Private Tour in Santorini by Luxury Catamaran

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...

9 to 11 hours Hotel pickup offered

5.0 (2)

from
$393

Santorini: Ios, Mykonos Full-Day Private Sailing Tour with Snacks

A classic island – hopping combination. Take the opportunity to visit them in one day! First, we visit Ios with a half an hour stop …More

Santorini, Greece

5.0 (2)

Santorini: Ios, Mykonos Full-Day Private Sailing Tour with Snacks

A classic island – hopping combination. Take the opportunity to visit them in one day! First, we visit Ios with a half an hour stop...

10 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$408

Shared Basic Sunset Trip of Santorini via Red Beach & White Beach

The cruise starts from Amoudi or Athinios port at 14:30 and sails below Caldera. First stop: Hot Springs for mud-bath. Sails past Aspronisi, Ancient light …More

Santorini, Greece

5.0 (1)

Shared Basic Sunset Trip of Santorini via Red Beach & White Beach

The cruise starts from Amoudi or Athinios port at 14:30 and sails below Caldera. First stop: Hot Springs for mud-bath. Sails past Aspronisi, Ancient light...

5 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$228

Paros Sunset Cruise with Traditional boat

Sail aboard the beautifully renovated Anna Maria, a traditional wooden boat, and discover the hidden coastline of northern Paros on an intimate sunset cruise. Away …More

Paros, Greece

5.0 (2)

Paros Sunset Cruise with Traditional boat

Sail aboard the beautifully renovated Anna Maria, a traditional wooden boat, and discover the hidden coastline of northern Paros on an intimate sunset cruise. Away...

2 hours 30 minutes Free Cancellation

5.0 (2)

from
$97

Private trip-Kleftiko Gerakas Tsigrado Paliochori with Speed Blue

During the trip drinks, food, salad, fruit are offered. There is comfort on the couch with or on the three different sunbeds of the boat, …More

Milos, Greece

5.0 (2)

Private trip-Kleftiko Gerakas Tsigrado Paliochori with Speed Blue

During the trip drinks, food, salad, fruit are offered. There is comfort on the couch with or on the three different sunbeds of the boat,...

5 hours Free Cancellation

5.0 (2)

from
$258

Private Cruise: PAROS – DELOS – RHENIA - MYKONOS

Departing from Paros and within an enjoyable boat trip, we reach the small port of Delos island, from which you can see the ancient monuments …More

Paros, Greece

5.0 (4)

Private Cruise: PAROS – DELOS – RHENIA - MYKONOS

Departing from Paros and within an enjoyable boat trip, we reach the small port of Delos island, from which you can see the ancient monuments...

8 hours Free Cancellation

5.0 (4)

from
$2,739

Discover the authentic charm of Tinos on a day trip from Mykonos, combining a scenic ferry journey with a guided island tour. Explore the island’s …More

Mykonos, Greece

5.0 (3)

Visit Tinos from Mykonos

Discover the authentic charm of Tinos on a day trip from Mykonos, combining a scenic ferry journey with a guided island tour. Explore the island’s...

9 hours Free Cancellation

5.0 (3)

from
$112

Paros Cruise to Antiparos & Despotiko with Traditional Boat

*The wooden boat Meraki has a length of 16 m. Maximum width of 5 m. It travels at 8.5 nm/hour and accommodates 42 passengers and …More

Paros, Greece

5.0 (3)

Paros Cruise to Antiparos & Despotiko with Traditional Boat

*The wooden boat Meraki has a length of 16 m. Maximum width of 5 m. It travels at 8.5 nm/hour and accommodates 42 passengers and...

7 hours Free Cancellation

5.0 (3)

from
$120

Day Cruise to Santorini from Paros Island

Santorini is the island of fire, according to the legend of Atlantis. It is the most photogenic island in the world, with its sparkling white …More

Paros, Greece

5.0 (2)

Day Cruise to Santorini from Paros Island

Santorini is the island of fire, according to the legend of Atlantis. It is the most photogenic island in the world, with its sparkling white...

11 hours Free Cancellation

5.0 (2)

from
$122

Discover the beautiful southern coastline of Mykonos on a relaxing cruise aboard a traditional Greek wooden boat. Enjoy three swimming stops in scenic bays, with …More

Mykonos, Greece

5.0 (3)

Mykonos South Coast Cruise with lunch

Discover the beautiful southern coastline of Mykonos on a relaxing cruise aboard a traditional Greek wooden boat. Enjoy three swimming stops in scenic bays, with...

8 hours Free Cancellation

5.0 (3)

from
$106

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

Milos, Greece

5.0 (4)

Private Boat Tour in Milos with Lunch

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

6 to 10 hours Free Cancellation

5.0 (4)

from
$1,826

Full Day Luxury Cruise on a De Antonio 42

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

5.0 (3)

Full Day Luxury Cruise on a De Antonio 42

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...

4 to 7 hours Free Cancellation

5.0 (3)

from
$2,296

Full Day Private Paros - Antiparos Tour with Luxurious Speed Boat

Embark on a private boat trip and visit Paros, Antiparos, and Despotiko. Swim in pristine waters, relax in isolated spots, and enjoy memorable views of …More

Paros, Greece

5.0 (3)

Full Day Private Paros - Antiparos Tour with Luxurious Speed Boat

Embark on a private boat trip and visit Paros, Antiparos, and Despotiko. Swim in pristine waters, relax in isolated spots, and enjoy memorable views of...

7 hours Free Cancellation

5.0 (3)

from
$1,249

Milos Private Half-Day Catamaran Cruise to Kleftiko with Lunch

Experience a private half-day cruise from Adamantas to Kleftiko aboard a luxurious sailing catamaran. Perfect for family, friends, special celebrations, with activities, dining, & breathtaking …More

Milos, Greece

5.0 (4)

Milos Private Half-Day Catamaran Cruise to Kleftiko with Lunch

Experience a private half-day cruise from Adamantas to Kleftiko aboard a luxurious sailing catamaran. Perfect for family, friends, special celebrations, with activities, dining, & breathtaking...

5 hours 30 minutes Free Cancellation

5.0 (4)

from
$2,755

Semipriv FishingTour on Kaiki Paros/Naousa or Private sunset tour

Departure at 10.00 from Naousa port and returns at 16.00. Under good weather conditions we sail outside Naousa Bay to collect the fishing nets were …More

Paros, Greece

5.0 (4)

Semipriv FishingTour on Kaiki Paros/Naousa or Private sunset tour

Departure at 10.00 from Naousa port and returns at 16.00. Under good weather conditions we sail outside Naousa Bay to collect the fishing nets were...

6 hours Free Cancellation

5.0 (4)

from
$127

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?