



Private sunset sail with a chef-prepared four-course dinner
3 – Hour
Up to 2 people
4-course dinner, beverages
Enjoy a private sunset charter aboard a luxury sailing yacht with a chef-prepared four-course dinner and included beverages as you cruise St. Augustine’s bayfront.
Deposit refundable up to 7 days prior. At 7 days prior, 50% is due/charged and deposits become non-refundable. At 72 hours prior, remaining balance is charged; all payments are non-refundable. Chef and food costs are non-refundable at 72 hours prior.
Dress for the forecasted weather. Wear smart casual clothing and consider bringing a light jacket or sweater since it can get breezy on the water.
Wear comfortable, non-marking, non-slip shoes. Avoid heels or black-soled shoes, since they can scuff the deck.
Yes. Each vessel has a head (bathroom).
3076 Harbor Drive, St Augustine Florida 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