Cyclades Islands Sailing Trips

153 Results
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 …More

Santorini, Greece

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
Private Daily Sailing Cruise to Discover the Highlights of Milos

This cruise is unique and a must when visiting Milos . It gets you to places mostly accessible only by boat and offer the comfort …More

Milos, Greece

This cruise is unique and a must when visiting Milos . It gets you to places mostly accessible only by boat and offer the comfort...

8 hours Free Cancellation
5.0 (34)
from
$1,318
Private half day cruise The Blue Lagoon with Paros Sail

You came to your vacation in Paros, there is one thing you must do! Sail and swim in the Blue Lagoon with Paros Sail. You …More

Paros, Greece

You came to your vacation in Paros, there is one thing you must do! Sail and swim in the Blue Lagoon with Paros Sail. You...

3 hours 30 minutes Free Cancellation
5.0 (38)
from
$1,357
Mykonos Catamaran Cruise with Meal Drinks and Sup

Go on a half-day cruise in the Aegean Sea. Select your preferred departure time morning or afternoon and sail to the mythical Delos and Rhenia …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Go on a half-day cruise in the Aegean Sea. Select your preferred departure time morning or afternoon and sail to the mythical Delos and Rhenia...

5 hours Free Cancellation
4.9 (14)
from
$1,370
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

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

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
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

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
Private Mykonos Catamaran Day Cruise with Meals & Water Toys

Choose between a morning or sunset cruise when booking. On the day, meet the skipper at Ornos Marina, finding a comfortable spot aboard the modern …More

Mykonos, Greece

Choose between a morning or sunset cruise when booking. On the day, meet the skipper at Ornos Marina, finding a comfortable spot aboard the modern...

5 hours Free Cancellation
4.9 (115)
from
$1,484
DREAM - Antiparos, Blue Lagoon & Despotiko (Private max 10 Pax)

Experience a beautiful sailing day around the Small Cyclades & Naxos. We sail all the way to our destination, stopping at various breathtaking locations and …More

Paros, Greece

Experience a beautiful sailing day around the Small Cyclades & Naxos. We sail all the way to our destination, stopping at various breathtaking locations and...

9 hours Free Cancellation
from
$1,589
Private Half Day Morning Cruise of Milos and Kleftiko

This private sailing cruise offers a premium, all-inclusive experience on a modern sailing yacht exclusively for you. With a dedicated captain and hostess on board, …More

Milos, Greece

This private sailing cruise offers a premium, all-inclusive experience on a modern sailing yacht exclusively for you. With a dedicated captain and hostess on board,...

6 hours 30 minutes Free Cancellation
5.0 (8)
from
$1,703
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

“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
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

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

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 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 …More

Milos, Greece

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
Glaraki Private Day Cruise

Our cruise starts with a delicious breakfast enjoyed on board while heading towards our first destination, Panteronisia / Blue Lagoon.  Once there, we will be surrounded …More

Antiparos, Greece

Our cruise starts with a delicious breakfast enjoyed on board while heading towards our first destination, Panteronisia / Blue Lagoon.  Once there, we will be surrounded...

6 hours 45 minutes Free Cancellation
5.0 (31)
from
$1,837
Luxury Private Power Catamaran Tour in Santorini

This is not a cookie-cutter approach to cruise sailing! Make your own schedule with us and choose the places you wish to see! Lucky 8 …More

Santorini, Greece

This is not a cookie-cutter approach to cruise sailing! Make your own schedule with us and choose the places you wish to see! Lucky 8...

3 hours
5.0 (7)
from
$1,837
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

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
DISCOVER - Tour Iraklia, Schinoussa & Naxos (Private max 10 Pax)

Immerse Yourself in the Beauty of the Small Cyclades Breathe in the fresh Aegean air and embrace the tranquility of the Small Cyclades. On this …More

Paros, Greece

Immerse Yourself in the Beauty of the Small Cyclades Breathe in the fresh Aegean air and embrace the tranquility of the Small Cyclades. On this...

9 hours Free Cancellation
from
$1,930
Mykonos Catamaran Private Delos Rhenia cruise

Indulge in this daily cruise to Delos and Rhenia islands, which lets you bask in the warm Mykonian sun, enjoying the summer breeze as you …More

Mykonos, Greece

Indulge in this daily cruise to Delos and Rhenia islands, which lets you bask in the warm Mykonian sun, enjoying the summer breeze as you...

6 hours Free Cancellation
4.9 (7)
from
$2,054
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

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
Private sailing cruise to Delos & Rhenia with Lunch & Transfer

Our first stop is an hour away, the renowned Big Delos island. While there, you will have the opportunity to visit one of the most …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Our first stop is an hour away, the renowned Big Delos island. While there, you will have the opportunity to visit one of the most...

6 hours Hotel pickup offered Free Cancellation
5.0 (12)
from
$2,227
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

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

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
Santorini Private Cruise to Volcanic Islands and Hot Springs

Sailing along the cliff at the north beautiful part of Santorini passing from Fira town - Imerovigli - Oia - Ammoudi - Thirassia - Volcano …More

Santorini, Greece

Sailing along the cliff at the north beautiful part of Santorini passing from Fira town - Imerovigli - Oia - Ammoudi - Thirassia - Volcano...

4 hours 30 minutes Hotel pickup offered Free Cancellation
from
$2,296

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