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+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
Aeolian Islands, Italy
One day to discover Aeolian Islands: The true Dolce Vita on a sailboat
Skipper included
Sailboat
7 hours
30 minutes
· For groups of up to 10 people
From
$1,684
$1,684
Rhodes Marina, Rhodes, Greece
5.0
(4)
Rhodes Private Luxury All-Day Sailing Cruise – Gourmet MediterAsian Lunch & Deluxe Dinner, Cocktails & Champagne
With skipper
Superowners
Sailboat
8 hours
· For groups of up to 8 people
Fuel included
Flexible cancellation
From
$1,391
$1,391
Instant Booking
Cala Jondal, Ibiza, España
5.0
(3)
Enjoy a full day of sailing in Ibiza and Formentera aboard a sailboat.
With skipper
Superowners
Sailboat
8 hours
· For groups of up to 12 people
From
$1,061
$1,061
Instant Booking
Tourlos Mykonos
4.9
(155)
Half-Day Cruise to Delos & Rhenia Islands – Mykonos
Skipper included
Superowners
Sailboat
5 hours
· For groups of up to 11 people
Fuel included
From
$943
$943
Instant Booking
Tourlos Mykonos
4.9
(155)
Full-Day Cruise to Delos & Rhenia Islands – Mykonos
Skipper included
Superowners
Sailboat
8 hours
· For groups of up to 11 people
Fuel included
From
$1,238
$1,238
Instant Booking
Molo Trapezoidale, Palermo, Italy
4.9
(3)
Sikelia Experience - Experience the Sea of Palermo: Sailing Experience with Gourmet Lunch or Dinner
Skipper included
Superowners
Sailboat
6 hours
· For groups of up to 12 people
Fuel included
From
$1,037
$1,037
Marina Nava, Split, Croatia
5.0
(43)
Private boat tour in Split, Brač and Šolta (8 hours)
With skipper
Superowners
Sailboat
8 hours
· For groups of up to 9 people
Fuel included
From
$825
$825
Instant Booking
Molo Trapezoidale, Palermo, Italy
4.9
(3)
Sikelia Private - Private Sailing Yacht in Palermo with Premium Services and a Chef on Board
Skipper included
Superowners
Sailboat
8 hours
· For groups of up to 12 people
Fuel included
From
$1,768
$1,768