Go Sailing in Amelia Island | Sailboat Charters, Classes & Rentals

Set your spirit free!

Fernandina Beach Getaway

Fun Sails

Private Charters

Want To Go Sailing? Sail on the beautiful waterways of Fernandina Beach, Amelia Island, FL to Cumberland Island and the Atlantic Ocean, with one of our USCG certified captains. Spot dolphins, wild horses, a variety of birds and more. Choose your time for your adventure, we are not limited by tides. Our charters are always private, only you and your guests with the captain.

Learn To Sail

Sailing Classes

Want to learn to sail? Our award winning sailing school consistently receives outstanding reviews from students. Our long-standing tradition of excellence is based on experienced instructors, bundle discounts and flexibility in scheduling to meet your needs.

Bareboat Charter

Sailing Rentals

Want To Go Sailing? We can tailor a bareboat charter package to suit your needs on our Hunter 34 or Voyage 37 Catamaran

Professional Photoshoot

Bring your photographer or ask us for recommendations on partner photographers.

Call us to book!

Celebrate your story with a breathtaking photoshoot on one of our beautiful boats. Experience the wind in your hair, and the golden sun on your face in a relaxed, intimate setting.

Loved every moment out on the water with Windward! Gorgeous evening, abundance of dolphins, amazing sunset. Highly recommend!

I took my ASA 104 sailing class with 2 of Windward Sailing captains (Roelie and Tony) who provided a combination of outstanding knowledge and experience bar none! I highly recommend their classes and would most definitely like to sail with them in the future!.

Always an enjoyable time and a knowledgeable crew. They are packed with information about the area and the boats and are happy to share that information with guests. We have sailed with them twice and will be back.

Fantastic experience. My father and I completed the ASA 101, 103, and 104 with Windward Sailing. Roelie, John, and Tony were very professional, informative, and friendly. They created an atmosphere fit for learning and having a great time. I feel very confident in my sailing knowledge/abilities after completing the ASA courses with Windward Sailing Club. I highly recommend this school!

Went sailing Day 1 with Capt Jason on the Hunter 32. Had a great time with my 3 grandchildren, daughter and my wife. Good winds a steady 10 knots gusting 20. The 4 hour sail went by fast. Thank you Windward team. Day 2. We Went on a sunset cruise on the Voyage Caramaran under Capt Roelie and his wife Sharon. What a lovely time and evening we all had. Even my son in law braved the time and enjoyed it. Thank you all

Go Sailing

Private Charter Are Great For Romantic Getaways, Family Memories, Social Events, and even Corporate Team Building.