Go Sailing (Fun Charters)
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Fun Sails Are Great For Romantic Getaways, Family Fun, Social Events and even Corporate Charters.
Relax and enjoy a sail… On the beautiful waterways of Fernandina Beach to Cumberland Island and the Atlantic Ocean. Choose your location and time.
- Go on a Adventure! Tour Around Amelia Island in One of Our Beautiful Sailboats
- Explore the beautiful Cumberland Sound See Dolphins, Fort Clinch, and Wild Cumberland Horses.
- Sail with One of Our Friendly USCG Licensed Captains.
- Up to 6 people or children on the sailboat(kids can ride too).
- Up to 10 passengers on the Catamaran. Charters for 7-10 passengers are considered bareboat charters. The charterer must sign a bareboat agreement and must provide their own USCG captain and mate approved by Windward Sailing, or select from pre-approved ones. Captain pay and gratuity go directly to the crew. A captain and mate are required for these charters. A portion of the booking fee will go toward fuel, and all food and drinks are provided by the charterer. Insurance over and above the vessel coverage is the sole responsibilty of the charterer.
- 48 hour cancellation policy. No charge for inclement weather cancellation(rain/lightning).
- There is a $50 extra premium charge per charter for holidays and holiday weekends.

2 Hour Sailboat Charter
2 passengers- $225 / $275 for 3-6 passengers
$225
- 2 Hour Sailboat charter

3 Hour Sailboat Charter
2 passengers- $299 / $325 for 3-6 passengers
$299
- 3-hour Sailboat Charter

4 Hour Sailboat Charter
2 passengers- $375 /$375 for 3-6 passengers
$375
- 4-hour Sailboat Charter

6 hour Sailboat Charter
2 passengers- $499 / $499 for 3-6 passengers
$499
- 6-hour Sailboat Charter
Sail on the Catamaran
$399 for 1-6 passengers ($50 per person over 6)
$399
- 2-hour Catamaran Sailboat Charter
- Relax and Lay on the Trampoline at the bow
- Charters over 6 passengers require 2 captains, and a 15% gratuity.
A "Three Hour" Catamaran Tour
$499 for 1-6 passengers ($50 per person over 6)
$499
- 3-hour Catamaran Sailboat Charter
- Charters over 6 passengers require 2 captains, and a 15% gratuity.
A "Four Hour" Catamaran Tour
$599 for 1-6 passengers ($50 per person over 6)
$599
- 4-Hour Catamaran Sailboat Charter
- Charters over 6 passengers require 2 captains, and a 15% gratuity.
Catamaran Overnight Rates
Overnight Rates (Including Captain) 6 Passengers Max
$1299
- 5pm-10am $1299 (max. 4 passengers)
- 24 hours @ $1699 (max. 4 passengers)
- seasonal (Labor Day through Memorial Day)
Over Night Yacht
Maximum 4 passengers
$899
- 8seasonal (Labor Day through Memorial Day
- 5pm to 10am @ $899 (maximum 4 passengers)
- Includes Dinner and a Light Breakfast
Over Night Yacht
Maximum 4 passengers
$1299
- 24 hours @ $1299 (max. 4 passengers)
- Includes 3 Meals
- seasonal (Labor day through Memorial Day).