Top Cyclades Islands Sailing Trips

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 →

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

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Enjoy a perfect sailing Sunset tour in the magnificent island of Santorini on board our catamaran. The catamaran sails to the most amazing sights of …More

Santorini, Greece

4.6 (1,021)

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Enjoy a perfect sailing Sunset tour in the magnificent island of Santorini on board our catamaran. The catamaran sails to the most amazing sights of...

5 hours Hotel pickup offered Free Cancellation

4.6 (1,021)

from
$90

Santorini Volcano and Hot Springs Cruise Tour from Fira Old Port

Your adventure begins at the old port of Fira, where you'll board a traditional boat to explore Santorini's volcanic wonders. The first stop is the …More

Santorini, Greece

4.3 (940)

Santorini Volcano and Hot Springs Cruise Tour from Fira Old Port

Your adventure begins at the old port of Fira, where you'll board a traditional boat to explore Santorini's volcanic wonders. The first stop is the...

3 hours Free Cancellation

4.3 (940)

from
$34

Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

Visit with licensed guide the natural insular archaeological site of Delos and enjoy swimming and snorkeling to a secluded cove off the uninhabited island of …More

Mykonos, Greece

4.7 (585)

Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

Visit with licensed guide the natural insular archaeological site of Delos and enjoy swimming and snorkeling to a secluded cove off the uninhabited island of...

5 to 6 hours Free Cancellation

4.7 (585)

from
$131

All inclusive cruise-Mykonos Delos&Rhenia beaches(free transport)

Experience the Joy of Sailing on a Yacht in a Friendly Small Group Atmosphere. Swim and Snorkel in Crystal Clear Waters, Indulge on Pristine Beaches …More

Mykonos, Greece

4.6 (122)

All inclusive cruise-Mykonos Delos&Rhenia beaches(free transport)

Experience the Joy of Sailing on a Yacht in a Friendly Small Group Atmosphere. Swim and Snorkel in Crystal Clear Waters, Indulge on Pristine Beaches...

6 hours Free Cancellation

4.6 (122)

from
$132

Santorini - Volcano and Hot springs Boat Trip with Bus Transfer

This iconic boat tour is the perfect choice if you're looking for an easy way to visit Santorini's famous volcano without spending more time and …More

Santorini, Greece

4.3 (75)

Santorini - Volcano and Hot springs Boat Trip with Bus Transfer

This iconic boat tour is the perfect choice if you're looking for an easy way to visit Santorini's famous volcano without spending more time and...

3 hours Free Cancellation

4.3 (75)

from
$51

Luxury Catamaran Semi private cruise with meals & drinks and transportation.

Take a break from the resort crowds and get offshore for a while on this chilled-out sailing excursion around Mykonos. Choose a trip to the …More

Mykonos, Greece

4.5 (42)

Luxury Catamaran Semi private cruise with meals & drinks and transportation.

Take a break from the resort crowds and get offshore for a while on this chilled-out sailing excursion around Mykonos. Choose a trip to the...

5 hours Hotel pickup offered Free Cancellation

4.5 (42)

from
$183

Τhis trip is mainly aimed at visitors who don't have much time to spare, ideal for cruise travelers, as the boat tour begins at the …More

Santorini, Greece

4.3 (36)

Santorini - Volcano and Hot springs

Τhis trip is mainly aimed at visitors who don't have much time to spare, ideal for cruise travelers, as the boat tour begins at the...

3 hours Free Cancellation

4.3 (36)

from
$34

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

Santorini Volcano Sunset Cruise with Dinner

Sail across Santorini’s beautiful ‘caldera’ (flooded crater) and visit the islands of Nea Kameni and Thirasia on this 6-hour cruise. Board a sightseeing boat from …More

Santorini, Greece

4.4 (27)

Santorini Volcano Sunset Cruise with Dinner

Sail across Santorini’s beautiful ‘caldera’ (flooded crater) and visit the islands of Nea Kameni and Thirasia on this 6-hour cruise. Board a sightseeing boat from...

6 hours 5 minutes Hotel pickup offered Free Cancellation

4.4 (27)

from
$129

DISCOVER - Iraklia, Schinoussa & Naxos (Shared max 10 People)

You will feel the smell of the Aegean Sea and breeze, and enjoy the relaxing beauty of the small Cyclades. During your full-day sailing trip, …More

Paros, Greece

4.7 (25)

DISCOVER - Iraklia, Schinoussa & Naxos (Shared max 10 People)

You will feel the smell of the Aegean Sea and breeze, and enjoy the relaxing beauty of the small Cyclades. During your full-day sailing trip,...

10 hours Free Cancellation

4.7 (25)

from
$193

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

Experience Santorini aboard a traditional wooden caique and discover the island's volcanic beauty through two unique cruise itineraries. Monday, Wednesday & Friday – Volcano & …More

Santorini, Greece

4.7 (6)

Santorini Volcanic Sunset Cruise

Experience Santorini aboard a traditional wooden caique and discover the island's volcanic beauty through two unique cruise itineraries. Monday, Wednesday & Friday – Volcano &...

4 to 6 hours Free Cancellation

4.7 (6)

from
$40

Santorini 3 Islands Trip Sailing Wooden Boat

A perfect tour to the islands of caldera with low cost is our trip that departs from the old port in Fira! ideal for cruise …More

Santorini, Greece

4.6 (5)

Santorini 3 Islands Trip Sailing Wooden Boat

A perfect tour to the islands of caldera with low cost is our trip that departs from the old port in Fira! ideal for cruise...

5 hours 45 minutes Free Cancellation

4.6 (5)

from
$40

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

Santorini Volcanic Islands Cruise: Volcano, Hot Springs and Thirassia

Morning visit to Volcano and its sulfur waters on a Traditional Greek Caique Boat. The first stop of your adventure is the volcano of Santorini, …More

Santorini, Greece

4.1 (198)

Santorini Volcanic Islands Cruise: Volcano, Hot Springs and Thirassia

Morning visit to Volcano and its sulfur waters on a Traditional Greek Caique Boat. The first stop of your adventure is the volcano of Santorini,...

6 hours Hotel pickup offered Free Cancellation

4.1 (198)

from
$57

Santorini Volcanic Islands Cruise: Volcano,Hot Springs,Thirassia and Oia Sunset

Morning visit to Volcano and its sulfur waters on a Traditional Greek Caique Boat. The first stop of your adventure is the volcano of Santorini, …More

Santorini, Greece

4.1 (94)

Santorini Volcanic Islands Cruise: Volcano,Hot Springs,Thirassia and Oia Sunset

Morning visit to Volcano and its sulfur waters on a Traditional Greek Caique Boat. The first stop of your adventure is the volcano of Santorini,...

11 hours Hotel pickup offered Free Cancellation

4.1 (94)

from
$65

Come onboard and enjoy the breathtaking Mykonian sunset! Set sail and enjoy the magnificent view of Little Venice and Mykonos. Drop anchor to watch the …More

Mykonos, Greece

4.2 (64)

Mykonos Sunset Cruise with Drinks

Come onboard and enjoy the breathtaking Mykonian sunset! Set sail and enjoy the magnificent view of Little Venice and Mykonos. Drop anchor to watch the...

2 hours 15 minutes Free Cancellation

4.2 (64)

from
$57

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

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 Sailing Trips?

What are the best kid-friendly options for Cyclades Islands Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Cyclades Islands Sailing Trips are:

View all kid-friendly Tours →

Which Cyclades Islands Sailing Trips have Instant Confirmation?

Cyclades Islands Sailing Trips with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Cyclades Islands Sailing Trips have Free Cancellation?

Cyclades Islands Sailing Trips 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 Sailing Trips have Hotel Pickup?

No problem. These Cyclades Islands Sailing Trips 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?