Sailing & Sunset Cruises with St Augustine Sailing

St. Augustine Sailing offers a distinctive gateway onto Florida’s historic waterways, where the meeting of Atlantic breezes and timeless shorelines paints a dynamic outdoor experience. Located in the nation’s oldest city, St. Augustine, this local sailing outfitter pairs scenic day sails and educational courses with curated luxury trips, carving out a unique niche in coastal adventure offerings.

The city itself is a mosaic of Spanish colonial architecture and natural coastlines, where ancient oaks and salt marshes meet the vast Atlantic Ocean just beyond a storied bayfront promenade. St. Augustine Sailing capitalizes on this setting, offering private and shared charters that range from tranquil sunset dinners and wine-and-food tasting cruises to hands-on sailing instruction certified through the American Sailing Association (ASA).

Key trips such as the "Sunset Tasting Cruise" and "Private Luxury Brunch Sail" provide immersive ways to appreciate the shifting colors of the sky and sparkling waters, often accompanied by the sight of wild dolphins weaving through the waves. Meanwhile, the "Nights of Lights" packages light up the night with sails through one of Florida’s most celebrated holiday displays, creating lasting memories amid glittering reflections.

For those wishing to learn, St. Augustine Sailing provides comprehensive beginner to advanced ASA-certified courses covering keelboat sailing, coastal cruising, catamaran handling, and essential marine skills. Experienced captains like Dan and Lauren bring professional guidance that’s attentive yet approachable, evidenced in glowing customer testimonials praising their knowledge and friendliness.

Whether you’re after romance with a "Sweetheart" sail package or an educational introduction with "Intro To Sailing," this outfitter crafts personal moments out on the water. Perfectly blending historical charm with active recreation, St. Augustine Sailing firmly anchors itself as a premier choice for those looking to engage with Florida’s coastal beauty in an authentic and memorable way.