Sailing in Grand Cayman

2 boats available

The best out of 2 deals in Grand Cayman - enter dates to check availability

Top Sailing in Grand Cayman

Showing top 2 charters
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Listing image
Meet the Captain
Sailing silhouette

55 ft

up to 20

Point Blue Sailing – Sensible

5.0
/5
(1 review)
 
George Town
4 Hour – Adventure Charter (9AM)
Embark on a boating adventure that combines excitement, relaxation, and unforgettable experiences! Swim alongside friendly stingrays in their natural habitat, sail through crystal-clear waters, and unwind at a picturesque sandbar. Whether you’re snorkeling, sunbathing, or simply soaking in the stunning surroundings, this trip offers something for everyone. Perfect for families, couples, or groups looking to create lasting memories on the water!
Price for up to 15 people
US $1,600
Listing image
Sailing silhouette

47 ft

up to 15

Blue Sky Sailing, Splendour in the Wind

5.0
/5
(2 reviews)
 
West Bay
4 Hour – Half Day Charter
A full-on Caribbean sailing experience, in half the time. Your half-day sail includes 2 snorkel stops in the North Sound, where you feed and swim with the stingrays at the original Stingray City. Then visit the Captain’s secret spot, “Orneil’s Aquarium”, which you won’t find on any map, but it’s teeming with local marine life.
Instant Confirmation
Price for up to 15 people
US $1,400
Listing image
Meet the Captain
Sailing silhouette

55 ft

up to 20

Point Blue Sailing – Sensible

5.0
/5
(1 review)
 
George Town
4 Hour – Adventure Charter (9AM)
Embark on a boating adventure that combines excitement, relaxation, and unforgettable experiences! Swim alongside friendly stingrays in their natural habitat, sail through crystal-clear waters, and unwind at a picturesque sandbar. Whether you’re snorkeling, sunbathing, or simply soaking in the stunning surroundings, this trip offers something for everyone. Perfect for families, couples, or groups looking to create lasting memories on the water!
Price for up to 15 people
US $1,600
Listing image
Sailing silhouette

47 ft

up to 15

Blue Sky Sailing, Splendour in the Wind

5.0
/5
(2 reviews)
 
West Bay
4 Hour – Half Day Charter
A full-on Caribbean sailing experience, in half the time. Your half-day sail includes 2 snorkel stops in the North Sound, where you feed and swim with the stingrays at the original Stingray City. Then visit the Captain’s secret spot, “Orneil’s Aquarium”, which you won’t find on any map, but it’s teeming with local marine life.
Instant Confirmation
Price for up to 15 people
US $1,400

Top Sailing Destinations

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Other great boat types in Grand Cayman

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