Sailing Class
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How we rank results
Listings are ranked based on a score that is recalculated every 24 hours using multiple criteria.
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Chania Old Port, Chania, Greece
4.9
(4)
Luxury at Sea / Catamaran in Chania
With skipper
Super owner
Catamaran
5 hours
· For groups of up to 15 people
From
$2,034
$2,034
Kissamos Port, Kissamos, Greece
4.9
(41)
Private Day Cruise To Balos And Gramvousa Island With Lunch
Skipper included
Sailboat
7 hours
30 minutes
· For groups of up to 10 people
Fuel included
Flexible cancellation
From
$1,436
$1,436
Ierapetra, Greece
5.0
(9)
65ft Luxury Motor Yacht Princess Shades Crete
With skipper
Super owner
Motorboat
5 hours
· For groups of up to 1 people
From
$2,991
$2,991
Special offer
79 experiences available
How we rank results
Listings are ranked based on a score that is recalculated every 24 hours using multiple criteria.
Learn more
Venetian Port, Heraklion, Greece
5.0
(3)
Golden Hour Escape: Sunset Sailing Experience to Dia Island
Skipper included
Sailboat
5 hours
30 minutes
· For groups of up to 8 people
Fuel included
Flexible cancellation
From
$574
$574
Instant Booking
Agios Nikolaos, Greece
5.0
(4)
"Mirabello Bay Supreme: A Luxury Maritime Adventure''
With skipper
Super owner
Catamaran
5 hours
· For groups of up to 1 people
From
$2,034
$2,034
Heraklion, Greece
5.0
(2)
5 Hours of Luxury at Sea in the waters of Heraklion, Crete
With skipper
Super owner
Catamaran
5 hours
· For groups of up to 1 people
From
$2,034
$2,034
Heraklion, Greece
5.0
(2)
Heraklion Morning Luxury Catamaran Experience — Dia Island (Crete)
With skipper
Super owner
Catamaran
6 hours
30 minutes
· For groups of up to 10 people
From
$1,496
$1,496
Vlychada marina, Santorini, Greece
5.0
(5)
Caldera Premium Private Cruise (full day)
Skipper included
Super owner
RIB
10 hours
· For groups of up to 6 people
Fuel included
Flexible cancellation
From
$2,991
$2,991
Instant Booking
Alimos Marina, Athens, Greece
5.0
(10)
Enjoy a day at sea in Athens on a sailboat
With skipper
Sailboat
9 hours
· For groups of up to 8 people
From
$1,064
$1,064
Souda, Greece
5.0
(33)
Unique Full-Day Experience: Total Relaxation and Stunning Coastal Views
Skipper included
Super owner
Motorboat
7 hours
· For groups of up to 8 people
Fuel included
Flexible cancellation
From
$945
$945
Lefkas Marina, Lefkada, Greece
5.0
(7)
Lefkada Full-Day Sailing Experience – Custom Cruise
Skipper included
Super owner
Gulet
8 hours
· For groups of up to 10 people
Fuel included
From
$1,196
$1,196
Rhodes Marina, Rhodes, Greece
5.0
(4)
Romance in Rhodes A Private Luxury Sunset Sailing Experience with Gourmet Vietnamese Cuisine, Premium C.A.I.R. Wine, Champagne & a Complimentary Signature Cocktail
With skipper
Super owner
Sailboat
4 hours
· For groups of up to 8 people
Fuel included
Flexible cancellation
From
$754
$754
Instant Booking
Kissamos Port, Chania, Greece
5.0
(23)
Discover Hidden Beaches and Ancient Views on a Relaxing Sailing Trip
Skipper included
Super owner
Sailboat
8 hours
· For groups of up to 10 people
Fuel included
From
$1,196
$1,196
Instant Booking
Rhodes Marina, Rhodes, Greece
5.0
(4)
Rhodes Luxury Private Sunset Dinner – MediterAsian Seafood Hot Pot
With skipper
Super owner
Sailboat
4 hours
· For groups of up to 8 people
Fuel included
Flexible cancellation
From
$838
$838
Instant Booking
Agios Sostis, Greece
5.0
(1)
Shipwreck, Secret Beaches, Caves & Turtles – 6 Hour Private Experience
With skipper
Super owner
RIB
6 hours
· For groups of up to 9 people
Flexible cancellation
From
$718
$718
Instant Booking
Souda, Greece
5.0
(33)
Cruise to Balos and Gramvousa: 11-hours of paradise and history.
Skipper included
Super owner
Motorboat
10 hours
30 minutes
· For groups of up to 8 people
Fuel included
Flexible cancellation
From
$2,572
$2,572
Rhodes Marina, Rhodes, Greece
5.0
(4)
Rhodes Private Luxury All-Day Sailing Cruise – Gourmet MediterAsian Lunch & Deluxe Dinner, Cocktails & Champagne
With skipper
Super owner
Sailboat
8 hours
· For groups of up to 8 people
Fuel included
Flexible cancellation
From
$1,388
$1,388
Instant Booking
Venetian Port, Heraklion, Greece
5.0
(5)
Sunset Dreams: A Magical Evening Cruise to Dia Island
Skipper included
Sailboat
6 hours
· For groups of up to 14 people
Fuel included
From
$838
$838