Sailing Experiences

The Fun Begins Where the Land Ends

St. Augustine charter sailing experiences beckon adventurers to discover the Ancient City through an unparalleled lens of luxury and excitement aboard one of our Captained sailing experiences.  Whether you seek seasonal sailings, private parties to celebrate, team-building excursions, or even the backdrop for a proposal or wedding, our extensive charter sailing experiences cater to diverse interests and occasions. Imagine chartering your own private sailing yacht, complete with a seasoned Captain at the helm, guiding you through the pristine waters with expertise and flair.

Elevating your time on the water is our priority, which is why we offer private catering services onboard all of our sailing charter experiences. Indulge in culinary delights as you soak in the breathtaking views and create memories to last a lifetime. Our fleet boasts top-of-the-line luxury sailing yachts, ensuring a comfortable and stylish journey for individuals or groups of any size.

What sets us apart is not just our state-of-the-art vessels but also our dedicated Captains and Crew. With a passion for sailing and a commitment to excellence, they are poised to provide you with a world-class sailing experience. Whether you’re a seasoned sailor or a first-time adventurer, our team will ensure your time on the water is nothing short of extraordinary.

So, why wait? Embark on a journey with St. Augustine Sailing and immerse yourself in the beauty and wonder of the Ancient City from the decks of our magnificent yachts. Your next unforgettable adventure awaits on the horizon.

FEATURED SAILINGS

ASA LESSONS

NIGHTS OF LIGHTS

SHARED & PRIVATE CHARTERS

CULINARY

LAND & SEA

Sunset Tasting Cruise

PHOTOGRAPHY

PROPOSALS & WEDDINGS

SAIL SCIENCE ADVENTURES

TEAM BUILDING

OVERNIGHT STAYS

LADYBUG EVENT
OPEN TO THE PUBLIC

Yachts in the harbor - Racing - Ladybug Race - Navigating the waves - Spring - Sailing - Sailing in St Augustine - Yachts

Join us for an exciting two-day celebration at St. Augustine Sailing!
May 3 explore our In-Water Boat Show featuring both new and pre-owned vessels, attend free marine workshops like Diesel 101, Medical Preparedness at Sea, Air Conditioning Maintenance, and more.

Enjoy a special Keynote Presentation by Tracy Edwards, renowned sailor and trailblazer.

On May 4th, don’t miss the One-Design Race – sign up to crew or hop aboard the spectator boat and cheer on the action!

Everyone is welcome – come be part of the fun!