Sail past St. Augustine’s evening lights aboard a private luxury yacht
2 hrs
Up to 10 people
Sweet & savory bites, hot drink
Step aboard a private luxury sailing yacht and watch St. Augustine light up from the water. Settle into the nighttime city views as your charter sails through the Ancient City’s festive glow.
This booking is for the whole experience, which fits up to 10 guests.
Cancel more than 72 hours before departure for a full refund. Cancellations 25–71 hours before departure forfeit the deposit; a $100 rescheduling fee applies. Within 24 hours, the full charter cost is retained. Dangerous-weather cancellations are exempt.
Product ID: YW85CW
Use the free parking available at the marina.
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
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