



Savor a chef-prepared four-course meal with drinks aboard a private luxury yacht at sunset
Discover what we've curated for you
Up to 6 people
Private yacht, Dinner, Beverages
Sail along the St. Augustine bayfront aboard a private luxury yacht as the sun sets. Enjoy a chef-prepared four-course dinner with wine, beer, or other beverages.
Please make your dinner selection 2 weeks before your charter. Arrive 15 minutes prior to departure for check-in and boarding. Dress for the forecast; vessels provide weather protection.
Deposit is fully refundable up to 7 days before the charter. From 7 days prior, a 50% non-refundable payment is due. At 72 hours, the remaining balance is charged and all payments are non-refundable. If weather prevents departure, dinner will be served dockside.
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 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