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Top trending Sailboats
How we rank results
Listings are ranked based on a score that is recalculated every 24 hours using multiple criteria.
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Tourlos Mykonos
Full-Day Sailing cruise: Up to 23 guests
With skipper
Superowners
Sailboat
7 hours
· For groups of up to 23 people
Flexible cancellation
From
$2,236
$2,236
Piso Livadi, Greece
Piso Livadi to Antiparos: Blue Lagoon & Beyond
Skipper included
Sailboat
8 hours
· For groups of up to 18 people
Fuel included
From
$2,589
$2,589
32 sailboats available
How we rank results
Listings are ranked based on a score that is recalculated every 24 hours using multiple criteria.
Learn more
Port Passenger Station, Heraklion, Greece
5.0
(1)
Morning or Sunset Adventure with Dufour 52
Skipper included
Superowners
Sailboat
4 hours
30 minutes
· For groups of up to 21 people
Flexible cancellation
From
$1,165
$1,165
Instant Booking
Venetian Port, Heraklion, Greece
5.0
(1)
Heraklion: Private Fullday sailing to Dia Island
Skipper included
Superowners
Sailboat
7 hours
· For groups of up to 21 people
Flexible cancellation
From
$1,706
$1,706
Instant Booking
Venetian Port, Heraklion, Greece
5.0
(1)
Sunset Sailing Experience – Dia Marine Area
Skipper included
Superowners
Sailboat
4 hours
30 minutes
· For groups of up to 21 people
Flexible cancellation
From
$1,165
$1,165
Instant Booking
Piso Livadi, Greece
Piso Livadi to Blue Lagoon: Half-Day Private Cruise
Skipper included
Sailboat
5 hours
· For groups of up to 18 people
Fuel included
From
$2,000
$2,000
Pantanassa, Greece
5.0
(1)
Private Coastal Sailing Playtime – Pantanassa
Skipper included
Superowners
Sailboat
3 hours
· For groups of up to 21 people
Flexible cancellation
From
$1,353
$1,353
Instant Booking
Port of Milos, Milos, Greece
4.8
(1)
Milos: Private luxury sailing to Kleftiko bay with Mediterranean Cuisine
With skipper
Superowners
Sailboat
5 hours
30 minutes
· For groups of up to 20 people
From
$1,765
$1,765
Special offer
Instant Booking
Venetian Port, Heraklion, Greece
New
Dufour 520 (Half-Day Trip)
Skipper included
Superowners
Sailboat
4 hours
30 minutes
· For groups of up to 21 people
From
$1,165
$1,165
Piso Livadi, Greece
Romantic Sunset Cruise from Piso Livadi toBlue Lagoon, Tripiti Bay and More!
Skipper included
Sailboat
5 hours
· For groups of up to 18 people
Fuel included
From
$2,000
$2,000
Rhodes, Greece
4.9
(7)
Your own Greek Odyssey: A 7h voyage on a sailboat
Skipper included
Superowners
Sailboat
7 hours
· For groups of up to 24 people
Flexible cancellation
From
$588
$588
Instant Booking