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 →

Private Cruise All Around Of Milos & Sunset to Klima Village

“Our private ‘All Around Milos & Sunset’ cruise is the perfect way to explore the island at your own pace. With your own captain and …More

Milos, Greece

5.0 (6)

Private Cruise All Around Of Milos & Sunset to Klima Village

“Our private ‘All Around Milos & Sunset’ cruise is the perfect way to explore the island at your own pace. With your own captain and...

12 hours Free Cancellation

5.0 (6)

from
$1,714

Full Day Boat Tour to Kleftiko & Sykia Cave

Our special trip is a full day tour gift to the soul, as you have the chance to witness virial historical monuments, by the sea, …More

Milos, Greece

5.0 (6)

Full Day Boat Tour to Kleftiko & Sykia Cave

Our special trip is a full day tour gift to the soul, as you have the chance to witness virial historical monuments, by the sea,...

8 hours Free Cancellation

5.0 (6)

from
$182

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

Private Sunset cruise to Rhenia&Little Venice with Mykonian Viand

Although not a day trip, this experience provides the perfect ending to a day in beautiful Mykonos. Set sail towards the horizon, with a glass …More

Mykonos, Greece

5.0 (5)

Private Sunset cruise to Rhenia&Little Venice with Mykonian Viand

Although not a day trip, this experience provides the perfect ending to a day in beautiful Mykonos. Set sail towards the horizon, with a glass...

4 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$1,370

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

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

Santorini Morning or Sunset Romance Private Sailing Volcano Tour

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a …More

Santorini, Greece

5.0 (4)

Santorini Morning or Sunset Romance Private Sailing Volcano Tour

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a...

6 hours Free Cancellation

5.0 (4)

from
$1,141

Private sailing cruise-Mykonos Southern Beach Hopping withLunch

Set Sail from Mykonos new port at 09:00 and enjoy the legendary Southern beaches of Mykonos (Ornos - Platys Gialos, Super Paradise, Elia, Agrari). Let …More

Mykonos, Greece

5.0 (3)

Private sailing cruise-Mykonos Southern Beach Hopping withLunch

Set Sail from Mykonos new port at 09:00 and enjoy the legendary Southern beaches of Mykonos (Ornos - Platys Gialos, Super Paradise, Elia, Agrari). Let...

6 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$1,722

Private Rhenia sailing cruise with Lunch & Transfer

Our team is highly qualified, with years of experience in the Greek waters; they are our home. Over the last decades, our business has included …More

Mykonos, Greece

5.0 (3)

Private Rhenia sailing cruise with Lunch & Transfer

Our team is highly qualified, with years of experience in the Greek waters; they are our home. Over the last decades, our business has included...

6 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$2,227

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

Private 2 Hours Sunset Cruise in Milos — Magical Klima Village

Heading to Klima promises not just a glimpse but a full immersion in nature's canvas at sunset. The way hues blend and dance across the …More

Milos, Greece

5.0 (3)

Private 2 Hours Sunset Cruise in Milos — Magical Klima Village

Heading to Klima promises not just a glimpse but a full immersion in nature's canvas at sunset. The way hues blend and dance across the...

2 hours Free Cancellation

5.0 (3)

from
$534

Private Cruise West Side of Milo's & Kleftiko

Our "West Side of Milos & Kleftiko" cruise offers a unique blend of natural beauty, historical exploration, and relaxation. Enjoy the privacy of the yacht …More

Milos, Greece

5.0 (2)

Private Cruise West Side of Milo's & Kleftiko

Our "West Side of Milos & Kleftiko" cruise offers a unique blend of natural beauty, historical exploration, and relaxation. Enjoy the privacy of the yacht...

7 hours 30 minutes Free Cancellation

5.0 (2)

from
$2,066

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

Private Mykonos Cruise: Rhenia Swim & Little Venice Sunset

Have you ever seen a sunset at Aegean ? Mykonos is not only known for wild nightlife and dancing, is also a very romantic destination, …More

Mykonos, Greece

5.0 (2)

Private Mykonos Cruise: Rhenia Swim & Little Venice Sunset

Have you ever seen a sunset at Aegean ? Mykonos is not only known for wild nightlife and dancing, is also a very romantic destination,...

4 to 5 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$746

Santorini Sailing for Cruise Guests A Volcano and Beach Tour

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a …More

Santorini, Greece

5.0 (2)

Santorini Sailing for Cruise Guests A Volcano and Beach Tour

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a...

6 hours Free Cancellation

5.0 (2)

from
$160

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

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

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

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
$1,492

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

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?

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

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?