Four-course dining and sunset views from a luxury sailing yacht
3 hrs
4 to 12 people
4-course dinner, drinks, sailing
Savor a chef-prepared dinner while sailing past the St. Augustine bayfront at sunset. Share the experience with fellow diners aboard a luxury yacht.
#Day of Your Sail
✅ Arrive & Check-In – Please check in 15-20 minutes before departure.
✅ Final Weather Check – Be aware of any last-minute weather updates.
✅ Transportation Coordination – Ensure timely arrival for check-in to avoid missing your departure.
#Dinner Cruise Experience
🍽 Personalized Dining – Guests will be guided to their tables upon boarding.
🥂 Welcome Beverage – Enjoy your first drink of choice once the safety briefing is complete and the vessel departs.
🌊 Scenic Dining – Relax as each course is served while sailing along the bayfront and river. Dessert is typically enjoyed on the return trip.
🐬 Spot Marine Life – Keep an eye out for dolphins and other marine wildlife during your voyage!
#Post-Sail Departure
✅ Wrap-Up & Docking – Gather your belongings and ask the crew any sailing-related questions.
📸 Share Your Experience! Tag @StAugustineSailing on social media and leave a review to share your adventure with others!
We look forward to welcoming you aboard for an unforgettable sailing experience!
Cancel at least 7 days before departure for a full refund. Within 7 days, deposits are nonrefundable; within 72 hours, all payments are nonrefundable. If dangerous weather prevents departure, dinner is served aboard the docked vessel.
Product ID: 3VEFVH
The shared dinner cruise requires at least four confirmed guests to sail. You do not need to book together; you may be paired with other diners.
Share specific dietary needs in advance. Accommodations may be possible, but are not guaranteed.
Custom cakes, flowers, photography, and upgraded wine selections are not included. These enhancements may be available for an additional charge.
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
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