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Rent A Sailboat

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Rentals Are For Verified Sailors: bareboat qualifications must be verified by a Windward Sailing captain.


4-Hour Rental

Monday - Friday
$250
  • Hunter-280 (28 ft. Shown Above)
  • Maximum 6 people
Hunter 34" Sailboat

4-Hour Rental

Saturday & Sunday
$300
  • Hunter-280(28 ft. Shown Above)
  • Maximum 6 people
View From the Stern of the Boat

8-Hour Rental

Monday-Friday
$350
  • Hunter-280(28 ft. Shown Above)
  • Maximum 6 people
A Sailboat Charter at Dusk

8-Hour Rental

Saturday & Sunday
$400
  • Hunter-280(28 ft. Shown Above)
  • Maximum 6 people

1 Night Rental

Monday-Sunday
$700
  • Hunter-280 (28 ft. Shown Above)
  • Maximum 6 people

Each Additional Night

Monday-Sunday
$200
  • Hunter-280(28 ft. Shown Above)
  • Maximum 6 people