


Sail past St Augustine landmarks on a 2-hour small-group charter
2 hour
2 to 6 people
2-hr shared sail, Crew onboard
Enjoy a 2-hour shared sail on a cozy sailboat and take in St Augustine’s waterfront skyline with a professional crew.
All alcohol must be purchased in the office prior to departure, and red wine is not available. Wear shoes with non-marking soles; hard soles, high heels, and black rubber soles are not allowed. Avoid spray tanning products, which can stain the boat.
Cancel before 72 hours: fully refundable. Cancel 71–25 hours: 50% of charter full cost non-refundable; $100 rescheduling fee applies. Cancel within 24 hours: full cost non-refundable. This does not apply to cancellation associated with dangerous weather conditions.
You need at least 2 guests to depart. The shared sail takes a maximum of 6 guests total, not including the captain and crew.
Arrive 10 minutes before departure so the team can greet you and accompany you to the vessel.
Wear shoes with non-marking soles (deck shoes, tennis shoes, or white-soled shoes). Avoid hard soles, high heels, and black rubber-soled shoes.
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