Windward Sailing — Fernandina Beach, FL
Cart FareHarbor 0 Checkout [Skip to content](https://windwardsailing.com/#content) ### Set your spirit free! #### Fernandina Beach Getaway - [(904) 441-9105](tel:19044419105) - [5 S Front St, Fernandina Beach, FL 32034](https://goo.gl/maps/hY67cqhYHpraKc397) Holiday Season Discounts ### Looking for great gift ideas? Give an unforgettable sailing experience with a 10% discount on all Gift Card Purchases through Dec 24 2025 Use Discount Code “Holiday2025” at checkout. [Gift card](https://fareharbor.com/embeds/book/windwardsailing/?full-items=yes&flow=667330&u=81f9dce1-6386-4455-aa49-0ed4c2b940b6&from-ssl=yes&ga4t=&g4=no&cp=no&csp=no&back=https%3A%2F%2Fwindwardsailing.com%2F) ## 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. [Discover More](https://windwardsailing.com/private-charters/) ## 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. [Discover More](https://windwardsailing.com/courses/) ## 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 [Discover More](https://windwardsailing.com/private-charters/)                     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 Tony Piche Loved every moment out on the water with Windward! Gorgeous evening, abundance of dolphins, amazing sunset. Highly recommend!  TorisaOGoogle Review 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!.  Dreamer538652TripAdvisor Review 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.  AmberLFacebook Review 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! GeorgeTGoogle Review 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 Tony Piche Loved every moment out on the water with Windward! Gorgeous evening, abundance of dolphins, amazing sunset. Highly recommend!  TorisaOGoogle Review ## Go Sailing Private Charter Are Great For Romantic Getaways, Family Memories, Social Events, and even Corporate Team Building **.** [Discover Our Fleet](https://windwardsailing.com/our-fleet/)