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St Augustine Sailing delivers exactly what you'd hope for in a maritime experience, with Dr. Dale and Captain Daniel earning particular praise for their expertise and warmth. Dr. Dale stands out as both a scientist and skilled instructor who runs everything from casual dolphin-watching tours to serious ASA certification courses. Reviewers consistently mention his teaching ability, patience (even calming someone through a panic attack during a maneuver), and deep knowledge of sailing mechanics. The Learn The Ropes courses seem especially popular, with multiple people mentioning how much they learned and feeling genuinely hooked on sailing afterward. Beyond the educational offerings, this outfit clearly knows how to create memorable outings. One couple raved about a wine and appetizer sail that included personalized touches like off-menu steaks, while families appreciated captains who let kids help raise sails and take the wheel. The boats themselves get compliments for their condition, and practical details like shade covers matter when you're out on Florida water. Wildlife sightings of dolphins and manatees add natural magic to the trips. Whether you want a romantic sunset cruise, a family adventure, or actual sailing instruction, the crew adapts well to different groups and consistently makes people feel welcomed rather than processed through a tourist experience.
I would personally love to thank RoseAnn , Derk and Daniel for making our night unforgettable. Every detail did not go unnoticed. You guys made our evening so magical and special.
Jeannie Money Binns
July 5, 2026
I would personally love to thank RoseAnn , Derk and Daniel for making our night unforgettable. Every detail did not go unnoticed. You guys made our evening so magical and special.
Jeannie Money Binns
July 5, 2026
Private 2-hour sunset sail past St. Augustine bayfront landmarks
Savor seasonal pairings while sailing into the sunset
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