Private 2-hour sunset sail past St. Augustine bayfront landmarks
2 hour
Up to 6 people
Private sunset sail, Crew
Set out on a private 2-hour sunset sail aboard a luxury yacht along the historic St. Augustine bayfront. Cruise past landmarks like the Castillo de San Marco, Bridge of Lions, and St. Augustine Lighthouse.
Maximum guests depend on the vessel. Alcohol must be purchased prior to departure; red wine is not available. Smoking and pets are not allowed on board.
Cancel before 72 hours: fully refundable. Cancel between 71–25 hours: 50% of charter cost non-refundable; $100 rescheduling fee. Cancel within 24 hours: full cost non-refundable. Policy notes this does not apply to cancellations associated with dangerous weather conditions.
Guest capacity depends on the vessel. One note lists a maximum of 6 guests per vessel (not including captain and crew). Some vessel options list maximums of 6, 8, or 10 people. Confirm which limit applies to the boat you choose.
Arrive 15 minutes before departure to collect life jackets for children (if needed) and to get provisions aboard.
No. Purchase all alcohol in the office prior to departure. Red wine is not available.
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