Top Cyclades Islands Sailing Trips

Q: What are the best options for Cyclades Islands Sailing Trips?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Cyclades Islands Sailing Trips are: Semi-private Day Cruise Santorini Semi-private Morning or Sunset Volcano Sailing Tour Mykonos 6hrs sailing cruise: Delos Rhenia with lunch & transfer A Boat Trip to the Pirate Caves & Blue Lagoon Santorini Fishing Private Cruise boat tour - BBQ, Snorkeling

Q: 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: Santorini Volcano Hot Springs Santorini - Volcano and Hot springs Santorini Volcano and Hot Springs Cruise Tour from Fira Old Port Santorini 3 Islands Trip by Sailing boat Santorini 3 Islands Trip Sailing Wooden Boat View all kid-friendly Tours →

Q: Which Cyclades Islands Sailing Trips have Instant Confirmation?

Cyclades Islands Sailing Trips with Instant Confirmation include: Santorini Volcano Hot Springs Santorini - Volcano and Hot springs Santorini Volcano and Hot Springs Cruise Tour from Fira Old Port Santorini 3 Islands Trip by Sailing boat Santorini 3 Islands Trip Sailing Wooden Boat View all Tours with Instant Confirmation →

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 →

Mykonos Half Day Cruise to Rhenia and Delos Islands with Meals

This cruise is perfect for lazy sleepers or people that have limited stay in Mykonos. During the half day cruise travellers would experience the joy …More

Mykonos, Greece

5.0 (2)

Mykonos Half Day Cruise to Rhenia and Delos Islands with Meals

This cruise is perfect for lazy sleepers or people that have limited stay in Mykonos. During the half day cruise travellers would experience the joy...

5 hours Free Cancellation

5.0 (2)

from
$98

Sparkling seas and secluded beaches? Join our Rhenia – Delos cruise and live a day like no other! The Cycladic Sisters, Mykonos, Delos and Rhenia, …More

Mykonos, Greece

4.8 (432)

The Authentic Rhenia-Delos Cruise

Sparkling seas and secluded beaches? Join our Rhenia – Delos cruise and live a day like no other! The Cycladic Sisters, Mykonos, Delos and Rhenia,...

6 hours 30 minutes Free Cancellation

4.8 (432)

from
$102

Luxury Santorini Catamaran Cruise: Lunch, BBQ, Drinks, Transfers

Our Santorini day cruise starts from the picturesque port of Vlychada, sailing onwards to explore the beauty of the Red Beach, White Beach, Indian Rocks, …More

Santorini, Greece

5.0 (447)

Luxury Santorini Catamaran Cruise: Lunch, BBQ, Drinks, Transfers

Our Santorini day cruise starts from the picturesque port of Vlychada, sailing onwards to explore the beauty of the Red Beach, White Beach, Indian Rocks,...

5 hours Hotel pickup offered Free Cancellation

5.0 (447)

from
$103

Boat and hike tour to the Hidden Beaches of Syros

Our adventure begins at Kini, a charming fishing village on Syros' west coast. We board a boat and leave behind everyday life, cruising toward the …More

Syros, Greece

5.0 (7)

Boat and hike tour to the Hidden Beaches of Syros

Our adventure begins at Kini, a charming fishing village on Syros' west coast. We board a boat and leave behind everyday life, cruising toward the...

5 hours Free Cancellation

5.0 (7)

from
$103

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

Santorini: Caldera Classic Semi-Private Cruise with BBQ & Drinks

The Day and Sunset Classic Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a …More

Santorini, Greece

5.0 (86)

Santorini: Caldera Classic Semi-Private Cruise with BBQ & Drinks

The Day and Sunset Classic Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a...

5 hours Hotel pickup offered Free Cancellation

5.0 (86)

from
$108

Agios Georgios | Greek Traditional Wooden Boat

Daily Morning Shared Cruise Full-day cruise to Blue Lagoon, Despotiko and a secluded bay: First stop: Greek dakos with local wine Second stop: BBQ onboard, …More

Paros, Greece

5.0 (6)

Agios Georgios | Greek Traditional Wooden Boat

Daily Morning Shared Cruise Full-day cruise to Blue Lagoon, Despotiko and a secluded bay: First stop: Greek dakos with local wine Second stop: BBQ onboard,...

7 hours 30 minutes Free Cancellation

5.0 (6)

from
$113

3-Hour Mykonos Best Beaches Yacht Cruise

Discover Mykonos from a different perspective aboard a sailing yacht and cruise along the island's world-famous south coast. This small-group experience is limited to just …More

Mykonos, Greece

5.0 (2)

3-Hour Mykonos Best Beaches Yacht Cruise

Discover Mykonos from a different perspective aboard a sailing yacht and cruise along the island's world-famous south coast. This small-group experience is limited to just...

3 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$114

Morning and Sunset Cruise with Meal and Transport Included

Choose between a morning or sunset cruise when booking. On the day, depart from your hotel via air-conditioned minivan to Mykonos' new port for the …More

Mykonos, Greece

5.0 (6)

Morning and Sunset Cruise with Meal and Transport Included

Choose between a morning or sunset cruise when booking. On the day, depart from your hotel via air-conditioned minivan to Mykonos' new port for the...

5 hours Free Cancellation

5.0 (6)

from
$114

South Coast Premium Sail Cruise with Lunch Drinks Swim and Sunset

This evening cruise is ideal for travelers that want to explore southern part of Mykonos passing through the worldwide famous bays, making couple of swimstops …More

Mykonos, Greece

4.9 (69)

South Coast Premium Sail Cruise with Lunch Drinks Swim and Sunset

This evening cruise is ideal for travelers that want to explore southern part of Mykonos passing through the worldwide famous bays, making couple of swimstops...

4 hours Free Cancellation

4.9 (69)

from
$114

2-Day Santorini Bus Tour with Volcanic Cruise

See all of the best of Santorini in this 2-day tour, visiting all must-sees and experience the island's culture before you go back home. Explore …More

Santorini, Greece

5.0 (3)

2-Day Santorini Bus Tour with Volcanic Cruise

See all of the best of Santorini in this 2-day tour, visiting all must-sees and experience the island's culture before you go back home. Explore...

2 days Free Cancellation

5.0 (3)

from
$115

5 Hours Sailing Trip to Mykonos Famous Beaches with Lunch

The opportunity to see all South beaches, soak up the sun, snorkel to crystal clear waters, and meet new people. The opportunity to explore the …More

Mykonos, Greece

5.0 (33)

5 Hours Sailing Trip to Mykonos Famous Beaches with Lunch

The opportunity to see all South beaches, soak up the sun, snorkel to crystal clear waters, and meet new people. The opportunity to explore the...

5 hours Hotel pickup offered Free Cancellation

5.0 (33)

from
$120

Santorini Oia: Small Group Day Cruise w BBQ Fresh Fish & Drinks

The Day Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay, is a great opportunity to enjoy a sailing cruise …More

Santorini, Greece

5.0 (33)

Santorini Oia: Small Group Day Cruise w BBQ Fresh Fish & Drinks

The Day Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay, is a great opportunity to enjoy a sailing cruise...

4 hours Hotel pickup offered Free Cancellation

5.0 (33)

from
$120

All inclusive cruise Sailing Cruise to Delos&Rhenia beaches

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

4.8 (22)

All inclusive cruise Sailing Cruise to Delos&Rhenia beaches

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...

5 hours 30 minutes Free Cancellation

4.8 (22)

from
$121

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

Perfect Luxury Sailing experience in the magnificent island of Santorini with an amazing catamaran. Sailing in luxury and style on the biggest Lagoon Catamaran on …More

Santorini, Greece

4.9 (1,222)

Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

Perfect Luxury Sailing experience in the magnificent island of Santorini with an amazing catamaran. Sailing in luxury and style on the biggest Lagoon Catamaran on...

5 hours Hotel pickup offered Free Cancellation

4.9 (1,222)

from
$125

Catamaran Day & Sunset Cruises with meals Drinks and transportation

• Cruise Duration: 5.00 Hours • Choice of a Morning or Sunset Cruise • Swim and snorkeling stop (Snorkeling Equipment Included) • Snap photos of …More

Mykonos, Greece

4.9 (1,150)

Catamaran Day & Sunset Cruises with meals Drinks and transportation

• Cruise Duration: 5.00 Hours • Choice of a Morning or Sunset Cruise • Swim and snorkeling stop (Snorkeling Equipment Included) • Snap photos of...

5 hours Hotel pickup offered Free Cancellation

4.9 (1,150)

from
$125

Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

Explore Santorini's volcanic landscape by sea on this 5-hour sailing trip aboard a new luxury catamaran. With its sleek, diamond-like design and comfortable seating areas …More

Santorini, Greece

4.8 (412)

Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

Explore Santorini's volcanic landscape by sea on this 5-hour sailing trip aboard a new luxury catamaran. With its sleek, diamond-like design and comfortable seating areas...

5 hours Hotel pickup offered Free Cancellation

4.8 (412)

from
$125

Luxury Santorini Sunset Cruise: Dinner, BBQ, Open Bar, Transfers

Get ready for an incredible Santorini Sunset Catamaran Cruise! Our adventure kicks off from the charming port of Vlychada , where we'll sail through the …More

Santorini, Greece

4.9 (380)

Luxury Santorini Sunset Cruise: Dinner, BBQ, Open Bar, Transfers

Get ready for an incredible Santorini Sunset Catamaran Cruise! Our adventure kicks off from the charming port of Vlychada , where we'll sail through the...

5 hours Hotel pickup offered Free Cancellation

4.9 (380)

from
$126

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

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

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?

Which Cyclades Islands Sailing Trips have 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?