

Sail into sunset views of St Augustine landmarks on a small-group charter
2 hour
2 to 12 people
2-hr sunset sail, Crew onboard
Set out on a 2-hour shared sunset sail with a professional crew and enjoy views of St Augustine’s waterfront landmarks.
At least 2 guests are required to depart. Smoking and pets are not allowed onboard.
Cancel before 72 hours: full refund of your deposit. Cancel 71–25 hours: 50% of charter full cost is non-refundable. Cancel within 24 hours: full cost is non-refundable. Rescheduling fee of $100 between 71–25 hours.
Wear shoes with non-marking soles (deck shoes, tennis shoes, or white-soled shoes). Avoid hard soles, high heels, and black rubber-soled shoes.
Purchase all alcohol in the office before departure. Red wine is not available.
Food and beverages are available for purchase.
3076 Habor 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.
Great experience. Great views. Great food. Great wine. Great staff. Great fellowship, Salute to Captain Kevin . We’d definitely do it again.
gerald bates
May 17, 2026
Great experience. Great views. Great food. Great wine. Great staff. Great fellowship, Salute to Captain Kevin . We’d definitely do it again.
gerald bates
May 17, 2026