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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
$2,239
$2,239
Marina di Rimini, Rimini, Italia
5.0
(1)
Riviera Romagnola Full Day by Boat
With skipper
Superowners
Sailboat
8 hours
· For groups of up to 20 people
Flexible cancellation
From
$943
$943
Instant Booking
60 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 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
$1,768
$1,768
Special offer
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
$1,167
$1,167
Instant Booking
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
$2,593
$2,593
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
$1,167
$1,167
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
$2,004
$2,004
Cadaqués, Spain
5.0
(5)
Full-day sailing trip to Cadaqués
Skipper included
Superowners
Sailboat
7 hours
· For groups of up to 35 people
Fuel included
From
$2,764
$2,764
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
$2,004
$2,004
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
$1,355
$1,355
Instant Booking
Mandraki Port, Rhodes, Greece
4.9
(22)
Luxury 6-Hour Sailing Adventure in Rhodes
Skipper included
Superowners
Sailboat
7 hours
· For groups of up to 24 people
Fuel included
From
$1,209
$1,209
Instant Booking