



See St Augustine landmarks on a private crewed sail
2 hours
Up to 6 people
Private sailboat, Captain and crew
Set sail on a private 2-hour cruise in St Augustine aboard a cozy sailboat with a professional crew. Take in scenic views and historic landmarks from the water.
Maximum 6 guests per vessel. Arrive 15 minutes early and wear non-marking shoes. No smoking or pets on board.
Free cancellation up to 72 hours before departure. Between 71–25 hours, 50% of the charter cost is nonrefundable and a rescheduling fee applies. Within 24 hours, the full cost is nonrefundable. This does not apply to cancellations for dangerous weather.
3076 Habor Drive, St Augustine, FL 32084
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