





Savor mimosas or seasonal wines while sailing St. Augustine’s scenic waterways with a captain
1 hour
Captain, Luxury sailing yacht
Sail St. Augustine’s waterways aboard a luxury yacht as you sip and take in coastal views. Choose morning, afternoon, or sunset departures for a relaxed cruise with friends.
A minimum of 2 guests is required to depart. Alcohol must be purchased in the office before departure; no red wine. Wear non-marking soles and avoid spray tanning products; no smoking or pets.
Free cancellation up to 72 hours before departure. 71–25 hours: 50% of the charter is nonrefundable; $100 rescheduling fee. Within 24 hours: full cost is nonrefundable. Weather-related cancellations are excluded.
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