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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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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
$2,639
$2,639
Piso Livadi, Greece
FULL DAY PRIVATE BBQ cruise – NAXOS AND THE SMALL CYCLADES
With skipper
Superowners
Sailboat
8 hours
· For groups of up to 23 people
From
$1,259
$1,259
+100 sailboats available
How we rank results
Listings are ranked based on a score that is recalculated every 24 hours using multiple criteria.
Learn more
Ornos, Greece
5.0
(46)
Bachelor Party Cruise
Skipper included
Superowners
Sailboat
5 hours
· For groups of up to 18 people
Fuel included
From
$756
$756
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
$1,799
$1,799
Special offer
Instant Booking
Marina of Porto Cervo, Porto Cervo, Italy
4.8
(33)
Aperitif at sunset
Owner as skipper
Superowners
Sailboat
3 hours
· For groups of up to 20 people
From
$1,439
$1,439
Instant Booking
Port de Sanary-Sur-Mer, Sanary-sur-Mer, France
4.9
(78)
Day of discovery of the islands and wild coves departing from Sanary-sur-Mer
Skipper included
Superowners
Sailboat
7 hours
· For groups of up to 20 people
Booked 4 times in the last 24h
Fuel included
Flexible cancellation
From
$972
$972
Special offer
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
$2,813
$2,813
Port de Sanary-Sur-Mer, Sanary-sur-Mer, France
4.9
(78)
Wine tasting towards sunset from Sanary-sur-mer
Skipper included
Superowners
Sailboat
3 hours
· For groups of up to 20 people
Booked 3 times in the last 24h
Fuel included
Flexible cancellation
From
$540
$540
Cala Gavetta, La Maddalena
4.8
(33)
The most beautiful sunset of the day, from the sea
Owner as skipper
Superowners
Sailboat
2 hours
30 minutes
· For groups of up to 20 people
From
$1,439
$1,439
Instant Booking
Milos, Greece
Sail the Whole Island Half a Day: Kleftiko, Poliegos & Milos Coastline
Skipper included
Sailboat
6 hours
· For groups of up to 22 people
Fuel included
From
$1,799
$1,799
Lelystad- Haven, Netherlands
Full Day Luxury Sailboat Experience – Lelystad
Skipper included
Sailboat
10 hours
30 minutes
· For groups of up to 120 people
Fuel included
From
$4,198
$4,198
Port Olímpic, Barcelona, Spain
Luxurious Vintage Sailboat Escape: 2h Barcelona Tour
With skipper
Sailboat
2 hours
· For groups of up to 65 people
Fuel included
From
$3,958
$3,958