Cyclades Islands Sailing Trips

150 Results
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

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
Mykonos Catamaran Private Sunset Cruise with Transfer

Trip Highlights 4 hours of sunset sailing Cruise with no engine noise Enjoy traditional Mykonian flavours onboard Enjoy beverages and drinks of your choice …More

Mykonos, Greece

Trip Highlights 4 hours of sunset sailing Cruise with no engine noise Enjoy traditional Mykonian flavours onboard Enjoy beverages and drinks of your choice...

4 hours Free Cancellation
5.0 (4)
from
$1,135
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

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

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 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
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

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

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

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
$531
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
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

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

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

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

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

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

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

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
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
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
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

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

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

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

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

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

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