Private 1-hour sailing date with bubbly, strawberries, and photos
1 Hour
Up to 10 people
Bottle of bubbly, Photos, Captain
Set out on a private 1-hour luxury sailing yacht charter in St. Augustine for a date night on the water. Your charter includes a captain plus bubbly, chocolate-covered strawberries, and a photographer.
All alcohol must be purchased in the office prior to departure; no red wines. Smoking is not allowed and pets are not permitted onboard.
This booking is for the whole experience, which fits up to 10 guests.
Cancel before 72 hours: fully refundable. Cancel between 71–25 hours: 50% non-refundable; $100 rescheduling fee. Cancel within 24 hours: full cost non-refundable. Dangerous weather exception applies.
Product ID: RBB6H3
Wear shoes with non-marking soles (deck shoes, tennis shoes, or white-soled shoes). Avoid hard soles, high heels, and black rubber-soled shoes.
Buy all alcohol in the office prior to departure. Beer, wine, and canned cocktails are available for purchase for guests 21+, and red wine is not available.
No. Smoking of any substance is not allowed on board.
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.
Took ASA103/104 with Dale, and it was a great class! Dale is an excellent teacher, methodical and good at explaining concepts through both physical demonstration and verbal explanations. There was a lot of information jammed into four days, and Dale prepared us well for both the exams and real life circumstances. Would have liked to sail more, but we were rained out one day, so there wasn't much to be done about that. If you're looking for a place to take ASA 103/104, I would highly recommend taking the combo class with St. Augustine Sailing. You'll get to practice sailing in the intracoastal waterway and the ocean!
Stephanie Weir
August 13, 2026
Took ASA103/104 with Dale, and it was a great class! Dale is an excellent teacher, methodical and good at explaining concepts through both physical demonstration and verbal explanations. There was a lot of information jammed into four days, and Dale prepared us well for both the exams and real life circumstances. Would have liked to sail more, but we were rained out one day, so there wasn't much to be done about that. If you're looking for a place to take ASA 103/104, I would highly recommend taking the combo class with St. Augustine Sailing. You'll get to practice sailing in the intracoastal waterway and the ocean!
Stephanie Weir
August 13, 2026
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