Savor seasonal pairings while sailing into the sunset
2 hours
Wine flight, appetizers, cruise
Sail the historic St. Augustine coastline as the sun sets, pairing each view with thoughtfully selected wines and seasonal flavors. Enjoy a tasting experience curated by sommelier Alayna Brewer aboard the Wind Dancer.
Your deposit is fully refundable up to 7 days before charter. Within 7 days, deposits are nonrefundable. Within 72 hours, all payments, including chef and food costs, are nonrefundable. In dangerous weather, the tasting is served dockside or in a private onsite room.
Product ID: QNPSEH
Yes, free parking is available in the marina.
This experience is best suited for adults due to the wine pairing
Yes, dietary preferences or allergies can often be accommodated with advance notice at the time of booking.
St. Augustine Sailing, 3076 Harbor Drive, St. Augustine, FL 32084
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
Sail St. Augustine’s historic bayfront as the sun sets from a private yacht
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