Windward Sailing

08/28/2024

Watching sunrise while docked at St Mary’s GA on an ASA 104 class. This never gets old!

08/19/2024

LIMITED TIME OFFER! Learn to sail with us this Fall! Book any ASA combo sailing course, mention this add, and we’ll throw in a Windward Sailing T-shirt as an additional incentive for completing your course and receiving your certification.

Windward Sailing offers American Sailing Association curriculum because we feel it best suits the needs of today's sailors and builds confidence, even in experienced sailors. These certifications are recognized for sailboat rentals. They also help to lower your insurance rates and are recognized by NASBLA and the Coast Guard as safe boating courses.

08/13/2024

“Batten down the hatches!” We had no choice but to face this terrifying but beautiful storm 10 miles offshore on our delivery run with our new boat, Windward’s Grace (Beneteau 393). 40 knots of wind and a deluge of water, but no problem with good storm prep and a solid crew eager to get home after a week of sailing.

07/11/2024

Gorgeous sunset and rainbow captured over Fernandina Harbor Marina this evening. Thanks captains Bill and Tony (and first/best mate Cindy) for sailing this evening in spots of rain ….

07/07/2024

Even Florida’s summer afternoon showers don’t dampen the beauty of a sunset charter. Thank you Cindy for this photo of Windwards Dream on a sunset cruise in the Cumberland Sound. Join us every day for a private charter on one of our three yachts and spot dolphins, horses, birdlife and more under sail!

05/30/2024

Tonight, two of Windward Sailing boats are out on seperate ASA 104 Bareboat Cruising courses anchored off St Mary’s GA and Fort George River FL. Sunsets are looking pretty good from both spots though!

05/27/2024

Remembering those that served with courage and valor.

05/25/2024

Summer storms bring their own rewards… This foto was taken as two cells merged over Fernandina Beach at sunset.

05/20/2024

Good friends, cold drinks, a fresh breeze and the best sunset Amelia Island has to offer …. Priceless!

05/14/2024

If you are an early riser you will not want to miss our sunrise cruise! Join the sh*****ng fleet and depart before dawn to see the sun rise over the ocean. Captain Jason Gerke recently grabbed a cup of coffee and headed out for a sunrise with a couple for Mothers Day.

05/11/2024

Looking for a fun / romantic excursion to Georgia via sailboat? We now offer Lunch and Dinner Cruises to St. Marys GA!

After leaving Fernandina Harbor Marina on the Amelia River and heading into the Cumberland Sound, you might spot a variety of wildlife, including dolphins / ray’s / rosette spoonbills / wood storks / pelicans / ospreys or bald eagles, not to mention the wild horses on Cumberland Island. We’ll head into the St. Marys river and experience the tranquility of marsh and wetland habitat. You can experience all of this under sail and as close to nature you one can get.

The five hour round-trip presents a lot of socializing time for you and your friends/family and one hour for lunch. The price for the charter on a monohull is $450, and $650 on the catamaran - both catering for up to 6 passengers. If you have additional passengers let us know so that we can accommodate them. Price excludes captain gratuity and lunch at a restaurant of your choice.

These charters require some planning so phone us well in advance of your planned lunch date to avoid disappointment!

04/24/2024

Beam reach in a 20 knot breeze - life is good!

03/18/2024

Windward Sailing’s fleet with Captain Gary’s “Salty Sally” out on the water today for a corporate charter. A light breeze prevented a competitive race but did not dampen the spirits on board, and our guests spotted some of Cumberland’s famous wild horses down on the beach. Thanks to Amelia Island Charter Boat Association for arranging.

02/25/2024

Doing some work in the rigging around sunset last night and saw Fernandina Beach Marina and the Windward Sailing fleet from a different perspective. Thanks to Captain Tony for doing the hard work on the winch.

02/02/2024

Sharing some photo’s from the last week - from cold and misty, to 25 knots of wind, to 80 degrees and sunny - got to love winter on Amelia Island!

01/25/2024

We recently had the pleasure of hosting a photo shoot with a great couple and photography crew. But why stop there - we can host a whole wedding with an officiant and up to 12 passengers/guests! Picking the right day is tricky but as these photo’s from Cheyenne Nichols shows, even a cloudy day out on the water provides many good photo opportunities!

01/11/2024

Time warp? On a Bareboat Cruising course tonight Captain Tony and students docked at St Mary’s GA and were treated to the sight of the Nao Trinidad, here untill January 14. Although suitably inspired, our crew have no plans to rival Maggelan’s circumnavigation feat because they have to home for dinner on Friday night.

01/02/2024

Sailing clinic dates for January (20th and 27th) and February (10th and 17th) now available. Join other students on our Hunter 34 for 3 hours of fun and hands-on learning with an ASA certified instructor. Call us at 904 441 9105 to reserve your slot - discounts available if you book multiple sessions!

01/01/2024

Happy New Year from Windward Sailing!

12/23/2023

Looking back on some memorable 2023 Amelia Island sailing experiences. Wishing all a very Merry Christmas!

12/23/2023

12/14/2023

A local pod of dolphins were so impressed with the quality of the sailing they came to inspect the vessel more closely. They found Captain Tony instructing Windward Sailing school students. Congratulations to the students for obtaining their ASA Basic Coastal Cruising certification!

11/27/2023

Want to improve your docking skills? Join us for the ASA 118 Docking Edorsement course. We don’t often host these - so grab the opportunity while it lasts! Limited availability for the all day class on December 18. Course fees include the study guide, testing and certification. ASA 101 required to avoid additional fees. Call to reserve your seat.

11/24/2023

Searching for the perfect gift this holiday season? Hard to beat quality time under sail in the beautiful Cumberland Sound! Give your loved ones an experience they won’t forget. Gift Cards are available on our website for a limited time at 10% discount. Click “Book Now” and use promo code “Sailgifts” at checkout for the perfect gift.

11/22/2023

Submarine pilot boat

11/22/2023

Happy Thanksgiving to the Navy!

11/18/2023

10/08/2022

Windwards Cat at sunset taken by our own Captain Bill Tighe

09/27/2022

Calm before the storm? Fernandina Harbor Marina

Sailing Charters, Lessons, and Rentals in Amelia Island, Florida.