Discover the serene beauty of St. Augustine during a Sunset Tasting Cruise with St Augustine Sailing. Enjoy breathtaking views, local wines, and a peaceful ocean voyage as the sun dips below the horizon. Perfect for a romantic evening or special celebration!
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–2.5 hours
Fitness Level
Suitable for most fitness levels; no strenuous activity required
Wildlife
History
St. Augustine is the oldest city in the U.S., with a rich maritime history dating back to the 16th century, making every water trip filled with historic significance.
Conservation
St Augustine Sailing emphasizes eco-friendly practices by minimizing waste and respecting local marine life during their tours.
St Augustine Sailing
Discover the serene beauty of St. Augustine during a Sunset Tasting Cruise with St Augustine Sailing. Enjoy breathtaking views, local wines, and a peaceful ocean voyage as the sun dips below the horizon. Perfect for a romantic evening or special celebration!
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 the Best Views
Getting to the dock 15-20 minutes early ensures you secure a good spot and settle in comfortably before sunset.
Bring Layers for Comfort
Evenings on the water can get breezy; packing a light jacket ensures you stay comfortable during the cruise.
Reserve in Advance
Sunset cruises are popular, so booking ahead guarantees your place for this exclusive experience.
Capture the Moment
Bring a camera or smartphone with a good zoom to capture the stunning coastal sunset and scenic views.
Sunscreen
Protect your skin from sun exposure during the cruise, especially on bright days.
summer
Hat and Sunglasses
Shield your eyes and face from the sun while enjoying outdoor scenery.
spring|summer
Light Jacket or Sweater
Stay warm during cooler evenings on the water with a comfortable layer.
fall|winter
Camera or Smartphone
Capture stunning sunset moments and scenic vistas during your cruise.