Cyclades Islands Sailing Trips

153 Results
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

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
$89
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
All inclusive cruise-Mykonos Delos&Rhenia beaches(free transport)

Experience the Joy of Sailing on a Yacht in a Friendly Small Group Atmosphere. Swim and Snorkel in Crystal Clear Waters, Indulge on Pristine Beaches …More

Mykonos, Greece

Experience the Joy of Sailing on a Yacht in a Friendly Small Group Atmosphere. Swim and Snorkel in Crystal Clear Waters, Indulge on Pristine Beaches...

6 hours Free Cancellation
4.6 (122)
from
$132
Santorini - Volcano and Hot springs Boat Trip with Bus Transfer

This iconic boat tour is the perfect choice if you're looking for an easy way to visit Santorini's famous volcano without spending more time and …More

Santorini, Greece

This iconic boat tour is the perfect choice if you're looking for an easy way to visit Santorini's famous volcano without spending more time and...

3 hours Free Cancellation
4.3 (75)
from
$51
Luxury Catamaran Semi private cruise with meals & drinks and transportation.

Take a break from the resort crowds and get offshore for a while on this chilled-out sailing excursion around Mykonos. Choose a trip to the …More

Mykonos, Greece

Take a break from the resort crowds and get offshore for a while on this chilled-out sailing excursion around Mykonos. Choose a trip to the...

5 hours Hotel pickup offered Free Cancellation
4.5 (42)
from
$183
Santorini - Volcano and Hot springs

Τhis trip is mainly aimed at visitors who don't have much time to spare, ideal for cruise travelers, as the boat tour begins at the …More

Santorini, Greece

Τhis trip is mainly aimed at visitors who don't have much time to spare, ideal for cruise travelers, as the boat tour begins at the...

3 hours Free Cancellation
4.3 (36)
from
$34
Small group,swim in Rhenia,watch the sunset fm LVenice, freetrans

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice, …More

Mykonos, Greece

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice,...

4 to 5 hours Hotel pickup offered Free Cancellation
4.6 (28)
from
$155
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

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
DISCOVER - Iraklia, Schinoussa & Naxos (Shared max 10 People)

You will feel the smell of the Aegean Sea and breeze, and enjoy the relaxing beauty of the small Cyclades. During your full-day sailing trip, …More

Paros, Greece

You will feel the smell of the Aegean Sea and breeze, and enjoy the relaxing beauty of the small Cyclades. During your full-day sailing trip,...

10 hours Free Cancellation
4.7 (25)
from
$193
Santorini 3 Islands Trip by Sailing boat

Enjoy the classic tour trusted by thousands of visitors to Santorini for decades. Ideal for cruise travelers, as the boat tour begins at the port …More

Santorini, Greece

Enjoy the classic tour trusted by thousands of visitors to Santorini for decades. Ideal for cruise travelers, as the boat tour begins at the port...

5 hours 30 minutes Free Cancellation
4.5 (8)
from
$40
Santorini Volcanic Sunset Cruise

Experience Santorini aboard a traditional wooden caique and discover the island's volcanic beauty through two unique cruise itineraries. Monday, Wednesday & Friday – Volcano & …More

Santorini, Greece

Experience Santorini aboard a traditional wooden caique and discover the island's volcanic beauty through two unique cruise itineraries. Monday, Wednesday & Friday – Volcano &...

4 to 6 hours Free Cancellation
4.7 (6)
from
$40
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
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
Santorini Volcanic Islands Cruise: Volcano, Hot Springs and Thirassia

Morning visit to Volcano and its sulfur waters on a Traditional Greek Caique Boat. The first stop of your adventure is the volcano of Santorini, …More

Santorini, Greece

Morning visit to Volcano and its sulfur waters on a Traditional Greek Caique Boat. The first stop of your adventure is the volcano of Santorini,...

6 hours Hotel pickup offered Free Cancellation
4.1 (198)
from
$57
Santorini Volcanic Islands Cruise: Volcano,Hot Springs,Thirassia and Oia Sunset

Morning visit to Volcano and its sulfur waters on a Traditional Greek Caique Boat. The first stop of your adventure is the volcano of Santorini, …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

Morning visit to Volcano and its sulfur waters on a Traditional Greek Caique Boat. The first stop of your adventure is the volcano of Santorini,...

11 hours Hotel pickup offered Free Cancellation
4.1 (94)
from
$65
Mykonos Sunset Cruise with Drinks

Come onboard and enjoy the breathtaking Mykonian sunset! Set sail and enjoy the magnificent view of Little Venice and Mykonos. Drop anchor to watch the …More

Mykonos, Greece

Come onboard and enjoy the breathtaking Mykonian sunset! Set sail and enjoy the magnificent view of Little Venice and Mykonos. Drop anchor to watch the...

2 hours 15 minutes Free Cancellation
4.2 (64)
from
$57
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
$1,593
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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These answers are based on answers previously given to Key West Private Charters customers' questions.

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