904-327-3265

Sailing Takes You Away!


Couple Kissing on a Sailboat at Dusk

Fun Sails – Sailing Charters

Want To Go Sailing? Go on the beautiful waterways of Fernandina Beach to Cumberland Island and the Atlantic Ocean, or sail from Jacksonville with one of our certified captains. Choose your location and time.

Man on Sailboat Learning to Sail

Learn To Sail – Sailing Classes

Want to learn to sail? Our sailing school is ranked in the top five sailing schools nationwide. Our long-standing tradition of excellence comes from adding more instruction options, discounts and total flexibility in scheduling.

A Group Renting A Sailboat for the Day

Rent A Sailboat

Want to rent a boat? For experienced or certified sailors, we offer sailboats without captains. You can choose your own sailing options while skippering your own chartered vessel. Proof of certification or a sailing resume is required.

Go Sailing with Windward
Call (904) 327-3265 or
Schedule an Appointment

Fun Sails Are Great For Romantic Getaways, Family Memories, Social Events and even Corporate Charters.

Windward's Catamaran in the Nassau Sound

Sail in the New Catamaran

2-Hours, Maximum 6 passengers
$300
  • Relax and Lay on the Trampoline at the Bow
  • A “Two Hour” Tour Around Amelia Island
  • Explore the beautiful Cumberland Sound
  • See Dolphins, Fort Clinch, and Wild Cumberland Horses
  • Sail with One of Our Friendly ASA & USCG Licensed Captains
Hunter 34" Sailboat

A "Two Hour" Tour Around Amelia

2-Hours, Maximum 6 passengers
$200
  • 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 ASA & USCG Licensed Captains
View From the Stern of the Boat

The "Extra Hour" Sailboat Tour

3-Hours, Maximum 6 passengers
$350
  • 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 ASA & USCG Licensed Captains
A Sailboat Charter at Dusk

Eight Hour Sailboat Charter

8-Hours, Maximum 6 Passengers
$500
  • 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 ASA & USCG Licensed Captains

Sailing Since 1997

Capt. Tony & Cindy Jones purchased Windward Sailing in the summer of 2005. They have been sailors in the Jacksonville area and around Northeast Florida for 30 years.

They are very proud of their enthusiastic, highly-qualified staff of United States Coast Guard Captains and American Sailing Association Certified Instructors!

Captain Tony Jones and his wife on a Sailboat
We are located in the seaport village of Fernandina Beach, in Northeast Florida, on beautiful Amelia Island — Florida’s northernmost barrier island. Just thirty minutes from Jacksonville International Airport, Amelia Island has been touted as one of America’s top ten destinations.