Top Cyclades Islands Cruises, Sailing & Water Tours

Santorini: Caldera Private Sailing Boat Cruise with Beneteau Oceanis 46.1

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number …More

Santorini, Greece

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number...

5 hours Hotel pickup offered Free Cancellation
5.0 (17)
from
$149
Santorini Full Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport

Enjoy unique views of Santorini from the sea during this 7 hour daycruise, starting from the port of Vlychada. Passing from the Red Beach you …More

Santorini, Greece

Enjoy unique views of Santorini from the sea during this 7 hour daycruise, starting from the port of Vlychada. Passing from the Red Beach you...

7 hours Hotel pickup offered Free Cancellation
4.9 (16)
from
$263
Sailsational Luxury Santorini Catamaran Sunset Cruise with Dinner

The limited number of participants makes this catamaran sailing experience unique and different. At most, 12-20 guests take place on this catamaran sailing tour. It …More

Santorini, Greece

The limited number of participants makes this catamaran sailing experience unique and different. At most, 12-20 guests take place on this catamaran sailing tour. It...

5 to 6 hours Hotel pickup offered Free Cancellation
4.8 (19)
from
$218
Maria Paros Sea Caves Tour Blue Lagoon Antiparos Despotico

The sea tour combines: A 3-4 stops for swimming and snorkeling , sunbathing on the deck listening music while finger food is served at the …More

Paros, Greece

The sea tour combines: A 3-4 stops for swimming and snorkeling , sunbathing on the deck listening music while finger food is served at the...

7 hours Free Cancellation
5.0 (15)
from
$100
Mykonos Delos Rhenia Cruise with Champagne Welcome

Your sailing adventure begins at the embarkation point in Mykonos, where our crew welcomes you on board with a safety briefing and a glass of …More

Mykonos, Greece

Your sailing adventure begins at the embarkation point in Mykonos, where our crew welcomes you on board with a safety briefing and a glass of...

5 hours Free Cancellation
5.0 (16)
from
$148
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
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
Santorini 5 Hours Private Day Or Sunset Tour with Bbq and Drinks

Charter a Private Yacht for an morning or evening of island adventure. You'll set sail from the port of Vlychada with a local captain, who …More

Santorini, Greece

Charter a Private Yacht for an morning or evening of island adventure. You'll set sail from the port of Vlychada with a local captain, who...

5 hours Hotel pickup offered Free Cancellation
5.0 (68)
from
$851
Best of Santorini Private Half-Day Catamaran Cruise with transfer and meal

Booking a Private Catamaran Tour in Santorini is a dream come true! We offer daily cruises to Santorini’s beautiful sights. The best way to spend …More

Santorini, Greece

Booking a Private Catamaran Tour in Santorini is a dream come true! We offer daily cruises to Santorini’s beautiful sights. The best way to spend...

5 hours Hotel pickup offered
5.0 (60)
from
$1,550
Private 5h Cruise Catamaran Santorini BBQ,drinks, transfer

You will be able to admire the beauty of the cruise around santorini and within the several location we will be stopping at. Enjoy a …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

You will be able to admire the beauty of the cruise around santorini and within the several location we will be stopping at. Enjoy a...

5 hours Hotel pickup offered Free Cancellation
4.9 (7)
from
$143
Luxury Caldera Cruise with a rich BBQ meal and drinks!

Sail along the southern coastline of Santorini and admire the lunar-like coastline of the island. At the picturesque Red Beach, dive into the crystalline waters …More

Santorini, Greece

Sail along the southern coastline of Santorini and admire the lunar-like coastline of the island. At the picturesque Red Beach, dive into the crystalline waters...

5 hours Hotel pickup offered Free Cancellation
4.6 (16)
from
$148
Private Morning Tour Lagoon 400-380 Sailing in Santorini,lunch, drink, transfer

Discover the most beautiful locations that Santorini has to offer on our beautiful Lagoon 400. Our crew will welcome you with open arms and provide …More

Santorini, Greece

Discover the most beautiful locations that Santorini has to offer on our beautiful Lagoon 400. Our crew will welcome you with open arms and provide...

5 hours Hotel pickup offered Free Cancellation
5.0 (62)
from
$162
Private Luxury Boat Tour from Mykonos to Delos & Rhenia – 4 Hours

Embark on an exclusive speed boat cruise in Mykonos, Greece, for an unforgettable journey around this enchanting island. With limited passengers, enjoy a personalized trip …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Embark on an exclusive speed boat cruise in Mykonos, Greece, for an unforgettable journey around this enchanting island. With limited passengers, enjoy a personalized trip...

4 hours Free Cancellation
4.8 (5)
from
$1,004
Private boat tour along the coastline of Santorini and volcano

If a tailor made cruise,away from crowds where you have to fight for an inch of space, is what you are looking for,look no further!Our …More

Santorini, Greece

If a tailor made cruise,away from crowds where you have to fight for an inch of space, is what you are looking for,look no further!Our...

4 hours Free Cancellation
5.0 (78)
from
$936
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
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
Santorini Volcano Cruise Including Hot Springs and Thirasia

Sail across Santorini’s beautiful ‘caldera’ (flooded crater) and visit the islands of Palea Kameni and Thirasia on this 4-hour guided boat tour. Board a sightseeing …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

Sail across Santorini’s beautiful ‘caldera’ (flooded crater) and visit the islands of Palea Kameni and Thirasia on this 4-hour guided boat tour. Board a sightseeing...

6 hours Hotel pickup offered Free Cancellation
4.4 (8)
from
$57
Thirassia Island: 6hr Private Tour with Lunch from Santorini

Come with us on a private tour to explore Thirassia. Meet the locals, walk through traditional paths and discover hidden cave houses! Are you ready …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

Come with us on a private tour to explore Thirassia. Meet the locals, walk through traditional paths and discover hidden cave houses! Are you ready...

5 hours Hotel pickup offered Free Cancellation
4.9 (8)
from
$194
Morning and Sunset Cruise with Meal and Transport Included

Choose between a morning or sunset cruise when booking. On the day, depart from your hotel via air-conditioned minivan to Mykonos' new port for the …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Choose between a morning or sunset cruise when booking. On the day, depart from your hotel via air-conditioned minivan to Mykonos' new port for the...

5 hours Free Cancellation
5.0 (6)
from
$114

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

Recent tour reviews
Activity name

Discover Cyclades Islands