THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Experience St. Augustine’s historic coastline on a relaxed sailing trip that blends stunning waterscapes with handcrafted cocktails. Discover why Sip & Sail is the go-to adventure for locals and visitors alike seeking coastal serenity and maritime charm.
Experience St. Augustine’s historic coastline on a relaxed sailing trip that blends stunning waterscapes with handcrafted cocktails. Discover why Sip & Sail is the go-to adventure for locals and visitors alike seeking coastal serenity and maritime charm.
Book with St Augustine Sailing
Verified experiences and guided adventures in the surrounding area.
Operated by St Augustine Sailing · St. Augustine, Florida
Set sail from historic St. Augustine, Florida, America's oldest city, on an unforgettable sailing adventure that pairs stunning coastal views with laid-back luxury. Sip & Sail offers a unique opportunity to experience the warm Atlantic breeze and striking shoreline from aboard a sleek sailboat, all while enjoying hand-crafted cocktails or your favorite beverages. This trip caters to adventurers and casual cruisers alike, delivering a serene escape that’s distinctively tied to St. Augustine’s maritime heritage.
As you glide along the Intracoastal Waterway and into the open sea, keep your eyes peeled for dolphins dancing in the bow wake or the graceful glide of pelicans. The flat waters and consistent coastal winds create ideal sailing conditions for a smooth ride even for first-timers. The boat itself is equipped with comfortable seating and shaded areas, making it an inviting space to relax and socialize. Experienced local captains skillfully navigate the vessel, sharing stories of the city’s rich nautical past and pointing out landmarks such as the iconic St. Augustine Lighthouse and the Castillo de San Marcos fortress.
Sip & Sail is more than just a boat tour; it’s an immersive way to unwind while connecting with the vibrant marine environment that defines this region. Guests often mention the unforgettable feeling of watching the sun sink behind the horizon, turning the sky into a canvas of pinks and oranges, all from the gentle rocking of the sailboat. Whether you’re looking for a romantic date idea, a fun outing with friends, or a peaceful solo retreat, this trip fills a niche among St. Augustine’s diverse outdoor activities.
What sets this experience apart is its blend of adventure and relaxation in a city better known for its historic streets than for water-based exploration. It offers an accessible entry point to Florida’s coastal ecosystem without the bustle of busier tourist spots. The captain’s insider knowledge enhances the journey with anecdotes about local wildlife, hidden coves, and the best dining spots back onshore.
Booking is simple via the referral link, with trips typically lasting 2 to 3 hours, perfect for a late afternoon or early evening slot. St. Augustine’s temperate climate means the season extends most of the year, providing ample chances to enjoy gentle breezes and unforgettable scenery. Dive into this maritime escape and discover St. Augustine from an entirely new perspective.
easy.
2–3 hours.
Suitable for all fitness levels; no sailing experience necessary.
No prior experience is needed; captains handle all sailing duties while guests relax and enjoy.
Select trips include cocktails or drinks, but you can also bring your own non-alcoholic beverages.
Cancellations typically require 24 hours’ notice—check with the operator for specific terms.
Children are welcome but should be supervised at all times aboard the boat.
Pets are generally not permitted due to safety and comfort regulations.
Bring sun protection, comfortable shoes, a light jacket for cooler evenings, and your camera.
St. Augustine, founded in 1565, is the oldest continuously inhabited European-established settlement in the continental United States.
Operators follow eco-friendly practices to minimize impact on marine life and encourage guests to respect local wildlife habitats.
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.
Book with St Augustine Sailing