

Sail at sunset past St Augustine landmarks with a small group and professional crew
2 hours
Up to 12 people
Captain & crew, Free parking
Make it a night to remember on a 2 hour small group sunset sail in St Augustine. Feel the ocean breeze as you pass landmarks like the Castillo de San Marco, the Bridge of Lions, and the St Augustine Lighthouse with a professional crew.
A minimum of 2 guests is required to depart; maximum 12 guests. Wear non-marking shoes and avoid hard soles, high heels, and black rubber soles. No pets or smoking on board; alcohol must be purchased in the office before departure.
Cancel 72+ hours before for a full refund of your deposit. Cancel 71–25 hours prior: 50% of the charter cost is non refundable. Cancel within 24 hours: full charter cost is non refundable. Rescheduling 71–25 hours prior incurs a $100 fee. Weather-related cancellations for dangerous conditions 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