cool shore excursions®
Top activities
Top landmarks
Trip ideas
Nearby places
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by time
  • Tours by the numbers
  • Top attractions
  • Santorini travel guides
  • Santorini travel calendar
  • Tours in nearby places
  • Explore Cyclades Islands tours
Language $Currency
Login / Sign up
Bookings
Bookings
Wallet
$0.00
Wishlists
Wishlists
Cool Rewards Rewards
Gift cards
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates

Top Santorini Sailing Trips

63 Results
Sort by:
Traveler Rating
Filter
Languages Clear
Time of Day Clear
50
43
3
Duration Clear
0
8
55
1
1
Price Clear
$0 $500+
Rating Clear
49
60
60
Specials Clear
60
8
0
26
3
Features Clear
41
37
55
0
39
9
Accessibility Clear
0
29
58
Families Clear
42
25
33

Santorini Tours

Attractions

Guides

Calendar

Sunset Caldera Sailing Cruise

Captain Yiannis and his crew -all experienced sailors- can assure you that all claims about greek hospitality are true and that this cruise will be …More

4.9 (87)

Sunset Caldera Sailing Cruise

Captain Yiannis and his crew -all experienced sailors- can assure you that all claims about greek hospitality are true and that this cruise will be...

5 hours Hotel pickup offered Free Cancellation
4.9 (87)
from
$144
Santorini Half Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport

Enjoy unique views of Santorini from the sea during this 5 hour morning or sunset cruise. Starting from the port of Vlychada, see the Vlychada …More

4.9 (87)

Santorini Half Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport

Enjoy unique views of Santorini from the sea during this 5 hour morning or sunset cruise. Starting from the port of Vlychada, see the Vlychada...

5 hours Hotel pickup offered Free Cancellation
4.9 (87)
from
$160
Santorini: Caldera Classic Semi-Private Cruise with BBQ & Drinks

The Day and Sunset Classic Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a …More

Likely to Sell Out
Likely to Sell Out
5.0 (86)

Santorini: Caldera Classic Semi-Private Cruise with BBQ & Drinks

The Day and Sunset Classic Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a...

5 hours Hotel pickup offered Free Cancellation
5.0 (86)
from
$108
Santorini: Small Group Catamaran Cruise with BBQ Fish & Drinks

The Day and Sunset Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a …More

Likely to Sell Out
Likely to Sell Out
4.9 (71)

Santorini: Small Group Catamaran Cruise with BBQ Fish & Drinks

The Day and Sunset Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a...

5 hours Hotel pickup offered Free Cancellation
4.9 (71)
from
$131
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

5.0 (62)

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...

5 hours Hotel pickup offered Free Cancellation
5.0 (62)
from
$163
Santorini Caldera Private Sailing Boat Cruise

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private …More

4.9 (53)

Santorini Caldera Private Sailing Boat Cruise

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private...

5 hours Hotel pickup offered Free Cancellation
4.9 (53)
from
$976
Explore Santorini and its volcanic wonders with Alex Private Boat

Join us on this breathtaking trip to Nea and Palea Kammeni,the lava islands in the middle of the crater. First up, we will see the …More

5.0 (48)

Explore Santorini and its volcanic wonders with Alex Private Boat

Join us on this breathtaking trip to Nea and Palea Kammeni,the lava islands in the middle of the crater. First up, we will see the...

3 hours Free Cancellation
5.0 (48)
from
$574
Santorini Oia: Private Sunset Cruise with Fresh Fish BBQ & Drinks

The Sunset Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay is a great opportunity to enjoy a sailing cruise at the …More

5.0 (46)

Santorini Oia: Private Sunset Cruise with Fresh Fish BBQ & Drinks

The Sunset Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay is a great opportunity to enjoy a sailing cruise at the...

6 hours Hotel pickup offered Free Cancellation
5.0 (46)
from
$209
Santorini Sunset Cruise in Caldera

Experience a calm and romantic trip to the amazing sites of Santorini on a charming wooden sailing boat! The peaceful atmosphere and gentle rocking of …More

4.9 (45)

Santorini Sunset Cruise in Caldera

Experience a calm and romantic trip to the amazing sites of Santorini on a charming wooden sailing boat! The peaceful atmosphere and gentle rocking of...

5 hours Free Cancellation
4.9 (45)
from
$52
Premium Santorini Private Day Tour Elba 45, BBQ, drinks, transfer

Explore the most attractive sights and beaches in Santorini on board the Luxurious Lagoon 450, exclusively for your party. Captain and crew will make this …More

4.9 (45)

Premium Santorini Private Day Tour Elba 45, BBQ, drinks, transfer

Explore the most attractive sights and beaches in Santorini on board the Luxurious Lagoon 450, exclusively for your party. Captain and crew will make this...

5 hours Hotel pickup offered Free Cancellation
4.9 (45)
from
$211
Santorini Private Catamaran Cruise

A Lagoon catamaran for your group only: up to 20 guests, 5 hours by day or at sunset from Vlychada Marina. Sail past Red Beach …More

5.0 (40)

Santorini Private Catamaran Cruise

A Lagoon catamaran for your group only: up to 20 guests, 5 hours by day or at sunset from Vlychada Marina. Sail past Red Beach...

5 hours Hotel pickup offered Free Cancellation
5.0 (40)
from
$184
Santorini Oia: Private Day Cruise with Fresh Fish BBQ & Drinks

The Private Day Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay is a great opportunity to enjoy a sailing cruise at the …More

5.0 (38)

Santorini Oia: Private Day Cruise with Fresh Fish BBQ & Drinks

The Private Day Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay is a great opportunity to enjoy a sailing cruise at the...

4 hours Hotel pickup offered Free Cancellation
5.0 (38)
from
$164
Morning Caldera Sailing Cruise

Step aboard this 5 hour morning cruise for a relaxed sail and enjoy your time swimming, sunbathing, snorkeling, taking photos, tasting delicious BBQ meals, Greek …More

5.0 (36)

Morning Caldera Sailing Cruise

Step aboard this 5 hour morning cruise for a relaxed sail and enjoy your time swimming, sunbathing, snorkeling, taking photos, tasting delicious BBQ meals, Greek...

5 hours Hotel pickup offered Free Cancellation
5.0 (36)
from
$144
Santorini Oia: Small Group Day Cruise w BBQ Fresh Fish & Drinks

The Day Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay, is a great opportunity to enjoy a sailing cruise …More

5.0 (33)

Santorini Oia: Small Group Day Cruise w BBQ Fresh Fish & Drinks

The Day Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay, is a great opportunity to enjoy a sailing cruise...

4 hours Hotel pickup offered Free Cancellation
5.0 (33)
from
$120
Santorini Semi-private Morning or Sunset Volcano Sailing Tour

Book your Santorini sailing tour to explore the volcano, hot springs, stunning views, and local flavors! …More

5.0 (22)

Santorini Semi-private Morning or Sunset Volcano Sailing Tour

Book your Santorini sailing tour to explore the volcano, hot springs, stunning views, and local flavors!...

5 hours Free Cancellation
5.0 (22)
from
$154
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

4.8 (19)

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...

5 to 6 hours Hotel pickup offered Free Cancellation
4.8 (19)
from
$218
Santorini Volcano Hot Springs

Visit Volcano & Hot Springs by joining our most popular & low cost tour. An experience you don't want to miss! ideal for cruise travelers, …More

4.8 (18)

Santorini Volcano Hot Springs

Visit Volcano & Hot Springs by joining our most popular & low cost tour. An experience you don't want to miss! ideal for cruise travelers,...

3 hours Free Cancellation
4.8 (18)
from
$34
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

5.0 (17)

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...

5 hours Hotel pickup offered Free Cancellation
5.0 (17)
from
$183
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

4.9 (16)

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...

7 hours Hotel pickup offered Free Cancellation
4.9 (16)
from
$262
Full Day Santorini Catamaran Private Cruise with meal and transfer

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

5.0 (16)

Full Day Santorini Catamaran Private Cruise with meal and transfer

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...

7 hours Hotel pickup offered
5.0 (16)
from
$2,526

Frequently Asked Questions

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

Recent tour reviews
View traveler photos & reviews
Activity name

Santorini Tours
Attractions
Guides
Calendar
View more