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Add dates to find your ideal boat for the best price
Top trending boats in Simpson Bay
How we rank results
Sint Maarten
New

Hanse - 418 | 9 people

(2020)
Skipper optional
Sailboats
9 people · 3 cabins · 9 berths · 12 m

From
$686
 / day

Sint Maarten
4.9
(5)

Jeanneau - 53 | 10 people

(2011)
Skipper mandatory
Super owner
Sailboats
10 people · 16 m

From
$103
 / day

Instant Booking
Full-day sailboat rental in Simpson Bay
Full-day sailboat rental in Simpson Bay
Full-day sailboat rental in Simpson Bay
Full-day sailboat rental in Simpson Bay
Full-day sailboat rental in Simpson Bay
Simpson Bay, Sint Maarten
5.0
(1)

Full-day sailboat rental in Simpson Bay

Skipper included
Super owner
Sailboat
8 hours · For groups of up to 10 people
Fuel included

From
$1,262

47 boats available
How we rank results
Marigot
4.9
(12)

Kirie - Feeling - 446 | 4 people

(1989)
Skipper optional
Super owner
Sailboats
4 people · 3 cabins · 4 berths · 14 m
Fuel included

From
$481
 / day

Marigot
New

- Moorings 464PC | 8 people

(2024)
Skipper optional
Super owner
Sailboats
8 people · 4 cabins · 8 berths · 14 m

From
$1,478
 / day

Special offer
Marigot
New

- Moorings 464PC | 8 people

(2026)
Skipper optional
Super owner
Sailboats
8 people · 4 cabins · 8 berths · 14 m

From
$1,352
 / day

Special offer
Marigot
New

Chantier naval aixois - Ketch | 10 people

(1989)
Skipper mandatory
Sailboats
10 people · 2 cabins · 6 berths · 12 m

From
$516
 / day

Marigot, Marigot Port
4.3
(7)

Beneteau - First 38 | 12 people

(1984)
With Skipper
Sailboats
12 people · 3 cabins · 8 berths · 12 m
Fuel included
Flexible cancellation

From
$566
 / day

Saint Martin
0.0
(0)

BENETEAU - OCEANIS 51.1 | 12 people

(2019)
Skipper optional
Sailboats
12 people · 6 cabins · 12 berths · 15.9 m

From
$519
 / day

Saint Martin
0.0
(1)

BENETEAU - OCEANIS 48 | 4 people

(2011)
Skipper optional
Sailboats
4 people · 4 cabins · 8 berths · 15 m

From
$1,374
 / day

Saint Martin
0.0
(0)

DUFOUR - 460 GL with watermaker | 12 people

(2019)
Skipper optional
Sailboats
12 people · 5 cabins · 10 berths · 14.2 m

From
$457
 / day

Saint Martin
4.7
(2)

Jeanneau - Sun Odyssey 45.2 | 4 people

(2003)
Skipper mandatory
Sailboats
4 people · 3 cabins · 5 berths · 13.8 m

From
$361
 / day

Saint Martin
5.0
(1)

Jeanneau - Sun Odyssey 40 | 6 people

(2003)
With Skipper
Sailboats
6 people · 3 cabins · 6 berths · 12 m
Fuel included

From
$85
 / day

Gustavia
New

Hanse - 445 | 8 people

(2013)
With Skipper
Sailboats
8 people · 3 cabins · 8 berths · 13.4 m
Flexible cancellation

From
$1,202
 / day

Gustavia
New

Bavaria - Bavaria45 cruiser | 4 people

(2010)
With Skipper
Sailboats
4 people · 2 cabins · 4 berths · 14.3 m
Fuel included

From
$961
 / day

Relax in Gustavia: 9h of sun on a sailboat
Relax in Gustavia: 9h of sun on a sailboat
Relax in Gustavia: 9h of sun on a sailboat
Relax in Gustavia: 9h of sun on a sailboat
Relax in Gustavia: 9h of sun on a sailboat
Relax in Gustavia: 9h of sun on a sailboat
Relax in Gustavia: 9h of sun on a sailboat
Relax in Gustavia: 9h of sun on a sailboat
Relax in Gustavia: 9h of sun on a sailboat
Relax in Gustavia: 9h of sun on a sailboat
Relax in Gustavia: 9h of sun on a sailboat
Gustavia, Saint Barthélemy

Relax in Gustavia: 9h of sun on a sailboat

Skipper included
Sailboat
9 hours · For groups of up to 8 people
Free cancellation

From
$2,163

Saint Barthélemy
0.0
(0)

Beneteau - First 40.7 | 10 people

(2008)
Skipper mandatory
Super owner
Sailboats
10 people · 3 cabins · 10 berths · 12.9 m
Fuel included

From
$1,030
 / day

Saint Barthélemy
5.0
(4)

JEANNEAU - SUN ODYSSEY 52.2 | 2 people

(2001)
Skipper optional
Super owner
Sailboats
2 people · 3 cabins · 6 berths · 15 m

From
$996
 / day

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