Windward Sailing

Windward Sailing School started in 1997 and has been an American Sailing Association affiliate school since 2000. We have won ASA Outstanding School 4 times and 3 of our instructors have received an ASA Outstanding Instructor award, certifying hundreds of sailors on the process. We currently have 9 certified ASA instructors.

Our sailing area offers deep water sailing inshore and offshore with easy access to the Atlantic. Our boats are docked on the Inter Coastal Waterway (ICW) and we are able to sail right off the dock and year-round.

Windward Sailing also offer private, captained charters, catering for romantic getaways, family fun, and social and corporate events. Whether you join us for a sail on one of our keelboats or stretch out on the trampoline of the catamaran, one of our friendly US Coast Guard licensed captains will share the magic of sailing as well as the sights and history of Amelia Island.

Explore the beautiful Cumberland Sound with its wildlife, Fort Clinch, and wild Cumberland Island horses. Extend your charter and we might venture into the Atlantic Ocean, or visit St Marys GA for lunch

  • Key Details
  • Discounts: Military
  • Hours of Operation:
  • MON: 9:00 AM - 5:00 PM
  • TUE: 9:00 AM - 5:00 PM
  • WED: 9:00 AM - 5:00 PM
  • THU: 9:00 AM - 5:00 PM
  • FRI: 9:00 AM - 5:00 PM
  • SAT: 9:00 AM - 5:00 PM
  • SUN: 9:00 AM - 5:00 PM



Award-winning American Sailing Association School

Weddings at Windward Sailing

Fun Sails Are Great For romantic getaways, family memories, social events, small weddings, and even corporate charters


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Meetings at Windward Sailing

We offer team building events and corporate regattas aboard sailboats, up to 7 boats at once. We sail from Fernandina Harbor Marina out to Cumberland Island, and beyond, into the ocean, or to St. Mary's, Georgia.

All of our charters are private. These are on sailboats with cabins below with restrooms.

Key Details:
  • Max Attendees: 22


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November 23, 2023

Exhilarating Sail!

I booked a 2 hr. charter with Windward Sailing for my husband and myself. The website wasn't giving me booking options so I called the number listed. I actually got a human being on the line! Sharon was wonderful in booking the day & time that worked best for us and could not have been more accommodating! We arrived at the dock early and our captain, Roulie, was already onboard and waiting for us. Mild temperatures but very erratic winds (up to 20+ knots) and strong currents. Less experienced sailors may have been flustered but Roulie was great! It was a fun and exhilarating sail! I highly recommend Windward Sailing. We'll be seeing them again.

November 06, 2023

Fantastic Fall bareboat charter on Windward's Hunter 34!

Six brothers had a reunion and bareboat chartered the Hunter 34 for an all-day sail. Gorgeous weather with moderate winds and some robust seas coming up the channel after several days of high NE winds before our sail. The boat was a great sailer, easily handling the seas and performed well both upwind heading north up the Cumberland Island coast and downwind on the return trip with diminishing winds. Saw many dolphins, sting ray breaching, and a sea turtle. Roelie provided concise instructions pre-sail without overkill as we were all experienced sailors. He also piloted the boat the first and last bits motoring in and out of the close quarters inside the marina, which we appreciated. First class operation, well maintained boat, great experience overall. Windward has our hearty endorsement!

October 13, 2023

Overnight bareboat rental

We booked an overnight bareboat rental with Windward. Roelie was very helpful in assessing weather/sea conditions, working through float plan options and prepping the boat for our trip. Though conditions did not allow us to make our initial plan, the experience with Windward was top notch. They were very flexible in helping us have a great time. Thanks!

October 09, 2023

Great time on the water - if you have sailed before or not

We booked a 2 hour tour with skipper (family of 4, kids 8y and 5y) - while I have been sailing many times it has been years ago and our kids never went. We really enjoyed our time on the water. Our skipper was very knowledgable and handled the boat with ease. We felt very welcome. The kids loved it - standing at the bow was great but being able to steer themselves was even better. We plan to come back

October 09, 2023

Great day, great captain.

We were on the catamaran, it's a great boat, plenty of room, will do it again very soon. The captain was a great guy.