Best results for Sailing in St Augustine, FL

Private 2-hour sunset sail past St. Augustine bayfront landmarks

Charter a luxury catamaran and enjoy a family-style brunch with bottomless mimosas

Share a brunch sail with mimosas on a 35 ft monohull in St. Augustine

Sail St. Augustine’s waterways with wine tasting or mimosas

Private 2-hour sunset sail for up to 6 in St. Augustine

Sail past St Augustine landmarks on a 2-hour small-group charter

Sail into sunset views of St Augustine landmarks on a small-group charter

Private 2-hour sail past St. Augustine’s historic bayfront sites

Sail St. Augustine waters and learn about dolphins with your guide

Learn sailing basics with classroom and dockside instruction

Learn sailing basics in a small group of 2–4 people

Build sailing confidence with a beginner-friendly 2-hour coaching sail

Build coastal navigation skills with a self-paced ASA 105 online course

Train as crew on Sunday sails with a USCG captain or ASA sailing instructor

Learn to skipper a keelboat in a two-day ASA 102 course

Practice coastal navigation theory in a four-day ASA course

Train to skipper a 30–50 ft sailboat on a 4-day ASA 106 course

Sail Saint Augustine at sunset with live music and complimentary drinks

Sail a 35-foot yacht and admire St. Augustine's dazzling Nights of Lights

Sail the Nights of Lights with dessert and a festive drink

Sail St. Augustine and swap book club notes over tea

Join a women’s sailing race team and practice on Zephyr

Sail at sunset with live music, drinks, and St. Augustine fireworks views