Sail beside St. Augustine's holiday lights with a chef-prepared four-course dinner
3 hrs
Up to 12 people
4-course dinner, house wine
Set out on a private luxury sailing charter as St. Augustine's lights come alive along the waterfront. Enjoy a front-row view from the water while sharing an upscale four-course dinner prepared by a private chef.
This booking is for the whole experience, which fits up to 12 guests.
Cancel 7+ days before your charter for a full deposit refund. Within 7 days, 50% of the charter cost is non-refundable; within 72 hours, all payments are non-refundable. Chef and food costs are non-refundable within 72 hours. If dangerous weather prevents departure, dinner is served dockside.
Product ID: 3GWB42
A waiver is required for this dinner cruise.
Warm, cozy blankets are available for purchase.
St. Augustine Sailing, 3076 Harbor Dr
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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