Cyclades Islands Sailing Trips

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

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
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 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
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
Santorini Sunset cruise

A peaceful romantic trip with the essence of a cruise to be unforgettable. Embark on this afternoon excursion! …More

Santorini, Greece

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
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
$1,492
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

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
$1,952
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
$1,263
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
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

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
3 Hours Private Sunset Tour in Greece with Free Drinks & Snacks

Close your eyes and create an image of setting sail towards the horizon with a glass of wine on hand, watching the sun dipping into …More

Mykonos, Greece

Close your eyes and create an image of setting sail towards the horizon with a glass of wine on hand, watching the sun dipping into...

3 hours Hotel pickup offered Free Cancellation
3.0 (2)
from
$86
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
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
Santorini Full-Day Private Experience: Sailing & Island Excursion

Enhance your visit to the world's most unique island with a full-day private tour of Santorini, and enjoy the opportunity to observe the island's beauty …More

Santorini, Greece

Enhance your visit to the world's most unique island with a full-day private tour of Santorini, and enjoy the opportunity to observe the island's beauty...

9 hours Hotel pickup offered Free Cancellation
from
$402
Full-Day Private cruise to Kleftiko, Polyaigos and Kimolos

Our cruises are one-way starting either in Agia Kyriaki beach and ending in Pollonia village or vice versa. We never sail back to our starting …More

Milos, Greece

Our cruises are one-way starting either in Agia Kyriaki beach and ending in Pollonia village or vice versa. We never sail back to our starting...

9 hours Free Cancellation
from
$1,148
Glaraki Private Sunset Tour

The unique breathtaking sunset in the Greek sea accompanied with traditional local snacks and drinks is the best way to relax on your vacations. …More

Antiparos, Greece

The unique breathtaking sunset in the Greek sea accompanied with traditional local snacks and drinks is the best way to relax on your vacations....

3 hours Free Cancellation
from
$1,033
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

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These answers are based on answers previously given to City Balloon Tours customers' questions.

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