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

Santorini Private Cruise Sightseeing Tour with BBQ and Drinks

Enjoy swimming & snorkeling in the clear blue waters of the Aegean Sea. You can go snorkeling near the shore and experience the amazing underwater …More

5.0 (13)

Santorini Private Cruise Sightseeing Tour with BBQ and Drinks

Enjoy swimming & snorkeling in the clear blue waters of the Aegean Sea. You can go snorkeling near the shore and experience the amazing underwater...

5 hours Free Cancellation
5.0 (13)
from
$170
Santorini Private Tour Half-Day Sailing Platinum Catamaran Cruise

This tour provides a complete experience of Santorini! You can swim in unique and otherwise impassable locations, enjoying the most wonderful of vistas while sailing …More

4.9 (9)

Santorini Private Tour Half-Day Sailing Platinum Catamaran Cruise

This tour provides a complete experience of Santorini! You can swim in unique and otherwise impassable locations, enjoying the most wonderful of vistas while sailing...

5 hours Hotel pickup offered Free Cancellation
4.9 (9)
from
$236
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

4.9 (7)

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...

5 hours Hotel pickup offered Free Cancellation
4.9 (7)
from
$144
Luxury Private Power Catamaran Tour in Santorini

This is not a cookie-cutter approach to cruise sailing! Make your own schedule with us and choose the places you wish to see! Lucky 8 …More

5.0 (7)

Luxury Private Power Catamaran Tour in Santorini

This is not a cookie-cutter approach to cruise sailing! Make your own schedule with us and choose the places you wish to see! Lucky 8...

3 hours
5.0 (7)
from
$1,837
Half day Private Sailing cruise in Santorini island up to 6 pax

Enjoy the cruise like a real sailor and experience moving with the force of the wind! Maria our captain will stand our, together with our …More

5.0 (6)

Half day Private Sailing cruise in Santorini island up to 6 pax

Enjoy the cruise like a real sailor and experience moving with the force of the wind! Maria our captain will stand our, together with our...

5 hours Free Cancellation
5.0 (6)
from
$1,033
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

5.0 (4)

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...

6 hours Free Cancellation
5.0 (4)
from
$1,141
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
5.0 (3)

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...

2 days Free Cancellation
5.0 (3)
from
$115
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

5.0 (2)

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...

6 hours Free Cancellation
5.0 (2)
from
$160
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

5.0 (1)

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...

5 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$1,263
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
4.6 (1,021)

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...

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

4.3 (940)

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...

3 hours Free Cancellation
4.3 (940)
from
$34
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

4.3 (75)

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...

3 hours Free Cancellation
4.3 (75)
from
$51
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

4.3 (36)

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...

3 hours Free Cancellation
4.3 (36)
from
$34
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

4.4 (27)

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...

6 hours 5 minutes Hotel pickup offered Free Cancellation
4.4 (27)
from
$129
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

4.5 (8)

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...

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

4.7 (6)

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 &...

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

4.6 (5)

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...

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

4.3 (3)

Santorini Sunset cruise

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

4.1 (198)

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,...

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
4.1 (94)

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,...

11 hours Hotel pickup offered Free Cancellation
4.1 (94)
from
$65

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