Join a private sunset sailing experience in St. Augustine and witness stunning coastal views as the sky transforms at sunset. Perfect for a romantic evening or small group celebration, this boat tour promises an unforgettable adventure on the water.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; no strenuous activity required
Wildlife
History
St. Augustine is the oldest city in the US, founded in 1565, with a rich maritime history reflected in its coastal waters and historic landmarks.
Conservation
St. Augustine Sailing is committed to eco-friendly practices, including responsible wildlife viewing and minimal impact sailing methods.
St Augustine Sailing
Join a private sunset sailing experience in St. Augustine and witness stunning coastal views as the sky transforms at sunset. Perfect for a romantic evening or small group celebration, this boat tour promises an unforgettable adventure on the water.
St Augustine Sailing operates premium sailing experiences and certified sailing courses in historic St. Augustine, Florida. The company offers a diverse lineup of public and private excursions — from shared brunch sails and sunset tasting cruises to intimate private dinner charters and wedding packages aboard luxury yachts. Educational offerings include ASA 103 Basic Coastal Cruising, Basic Keelboat prep classes, and hands-on day sails on 21–22-foot boats and larger Jeanneau models.
Each experience blends local maritime history, coastal wildlife viewing, and elevated hospitality. Professional skippers and trained crew lead all trips, delivering safety briefings, navigation expertise, and attentive service. On private dinner and tasting cruises, guests enjoy chef-prepared courses, sommelier-curated flights, and tailored menus served onboard. Photography-focused sails provide short portrait sessions against landmarks like the Lighthouse and Historic Bayfront.
St Augustine Sailing prioritizes safety and instruction for learners and recreational sailors. Courses emphasize seamanship, heavy-weather operation, docking skills, and practical boat handling on 30–45-foot auxiliary-powered catamarans. Short introductory sessions give beginners the confidence to handle sails and basic lines.
For weddings and private events, the company offers packaged options including on-yacht ceremonies, dockside Marriage Knot services, bouquets, photography, wedding cake, and charcuterie boards for small to mid-size groups. Vessel maintenance, certified instruction, and transparent booking policies support reliability and repeat business.
Located in downtown St. Augustine’s marina district, the operator leverages local knowledge of tides, wildlife patterns, and historic routes to create memorable, trustworthy coastal adventures for couples, families, learners, and food-and-wine enthusiasts. Bookings are available year-round with flexible cancellation policies online.
Tours Offered
14
Variety of sails and courses
Private Events
Up to 30 guests
Yacht and dock wedding options
Certified Courses
ASA 103 plus basics
Two-day and 3-hour classes available
Luxury Dining
Four-course dinners
Sunset cruises with gourmet meals
Reserve a sunset cruise, private dinner, wedding sail, or ASA course — secure dates fill quickly.
Arrive Early for Optimal Sunset Viewing
Getting to the dock 15-20 minutes early ensures the best spot on the boat and plenty of time to settle in before sunset.
Dress in Layers
Evenings can cool down quickly after sunset, so bring layers to stay comfortable on the water.
Bring a Camera or Smartphone
Capture the vibrant colors of the sunset and scenic views to cherish and share later.
Stay Hydrated and Bring a Beverage
Enjoy your favorite drink responsibly while relaxing aboard the boat for a more enjoyable experience.
Sunscreen
Protect your skin from UV rays during daytime before the sailing trip.
summer
Light Jacket or Sweater
Keep warm if temperatures drop after sunset or during breezy conditions.
spring|fall|winter
Binoculars
Enhance wildlife viewing opportunities onboard.
Reusable Water Bottle
Stay hydrated while enjoying your time on the water.