





Choose a morning or afternoon private sail for up to 5
9AM - 1PM or 1PM - 5PM
Up to 5 people
Set out on a half-day sailing session with morning or afternoon departure options. Enjoy a private day sail for up to five guests, subject to skipper requirements.
Maximum of five persons onboard, including any added captain. Skipper checkout approval is at the Staff Captain's discretion. Funds are non-refundable if the skipper does not meet minimum skill requirements to operate unaccompanied.
Cancel before 72 hours: fully refundable. Cancel between 71–25 hours: 50% of charter cost is non-refundable. Cancel within 24 hours: full cost is non-refundable. A rescheduling fee applies between 71–25 hours of charter. This does not apply to dangerous weather conditions.
3076 Harbor Dr,, St. Augustine, FL, 32084-2123
Discover what we've curated for you
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 day with the Crew! Kevin is an amazing captain and we learned quite a bit from him. Highly recommend him for people wanting to improve their sailing skills.
Rosser Pace
March 30, 2026
Great day with the Crew! Kevin is an amazing captain and we learned quite a bit from him. Highly recommend him for people wanting to improve their sailing skills.
Rosser Pace
March 30, 2026