With skipper Sailboat charter
Add dates to find your ideal boat for the best price
Top trending Sailboats
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
$1,681
$1,681
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
$1,681
$1,681
+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
Marina di Porto Rotondo
New
Costa Smeralda by Boat – Mortorio, Soffi, and Hidden Islands
Skipper included
Superowners
Sailboat
8 hours
30 minutes
· For groups of up to 4 people
Fuel included
From
$1,765
$1,765
Port de Dinard, Dinard, France
4.8
(19)
Relax in Dinard: 10 hours of sun on a sailboat
Owner as skipper
Superowners
Sailboat
10 hours
· For groups of up to 8 people
Fuel included
From
$500
$500
Porto Rotondo, Italy
5.0
(15)
9 hours of sailing along the coast of Porto Rotondo
With skipper
Superowners
Sailboat
9 hours
· For groups of up to 7 people
From
$1,412
$1,412
Instant Booking
Palau, Italy
4.9
(10)
Explore Palau and enjoy a full day of sailing
With skipper
Superowners
Sailboat
9 hours
· For groups of up to 9 people
Flexible cancellation
From
$458
$458
Instant Booking
Port Olímpic, Barcelona, Spain
4.8
(58)
Golden Hour on the Mediterranean: Barcelona at Dusk
With skipper
Superowners
Sailboat
2 hours
· For groups of up to 7 people
Flexible cancellation
From
$176
$176
Instant Booking
Palma de Mallorca, Spain
4.9
(2)
Premium experience on a brand new private yacht. Sailing in Palma Bay with snacks and drinks, including Coca-Cola, Fanta Orange, Cava Brut, Cabernet Sauvignon white wine, paddle surfing, and snorkeling kit. Swimming at Illetas and a coastal stroll.
Skipper included
Sailboat
4 hours
· For groups of up to 6 people
Fuel included
Flexible cancellation
From
$941
$941
Port des Mouettes, Évian-les-Bains, France
5.0
(32)
Full-day sailing trip to Évian-les-Bains
With skipper
Sailboat
6 hours
· For groups of up to 10 people
Flexible cancellation
From
$471
$471
Port de Deauville Trouville, Deauville, France
4.9
(78)
Discover Deauville on a full-day sailing trip
Owner as skipper
Superowners
Sailboat
12 hours
· For groups of up to 6 people
Fuel included
Flexible cancellation
From
$289
$289
Port Olímpic, Barcelona, Spain
4.8
(58)
The Perfect Escape: Swim, Sail & Slow Down - 2h - Best seller!
With skipper
Superowners
Sailboat
2 hours
· For groups of up to 7 people
Flexible cancellation
From
$141
$141
Instant Booking
Saint-Malo, France
5.0
(16)
Seize every moment: A full day of sunshine around Saint-Malo on a sailboat
Skipper included
Superowners
Sailboat
7 hours
· For groups of up to 11 people
Fuel included
From
$765
$765
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
$941
$941
Instant Booking
Puerto de Garrucha, Garrucha, Spain
5.0
(21)
Enjoy a two-day overnight trip to Cabo de Gata. Watch the sunset at Las Negras, Arrecife de las Sirenas, or Isleta del Moro. Spend the night in San José and stroll through its streets. Two full days. All included (food, drinks, and overnight stay in San José aboard the sailboat).
With skipper
Superowners
Sailboat
8 hours
· For groups of up to 10 people
Flexible cancellation
From
$882
$882
Instant Booking