Private Day Sail on St. Augustine’s Historic Bayfront: Explore Florida’s Oldest Port by Sea
Difficulty
easy
Duration
3–5 hours
Fitness Level
Light physical fitness is sufficient; mostly relaxing while on board
Overview
Set sail on a private day cruise across St. Augustine’s historic Matanzas Bay. Discover the city’s colonial past and coastal wildlife from the water’s edge—an unforgettable blend of history, nature, and calm sea breezes.
Private Day Sail Along Historic Bayfront
Starting at $595.00
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Adventure Photos
About This Adventure
Description
We invite you to sit back, relax and enjoy the beautiful view and wildlife as we slip away from the dock and sail down the Tolomato River. Make sure to look for dolphins as we approach Porpoise Point as we often see a lot of wildlife in this area. As we continue our sail down the Matanzas River toward the historic St Augustine Bay Front, you will get to experience the ancient city's historic sites from the water.
Bring your friends and family and get ready to enjoy adventure, or bring that special someone and experience a romantic getaway on your private, 2-hour charter aboard our luxury sailing vessel.
Let our professional staff of USCG licensed Captains welcome you and your guests aboard for an experience like no other in the beautiful city of St. Augustine!
Booking Disclaimers:
Maximum number of guests is 6 per vessel, not including captain and crew.
We offer convenient and free parking at the marina. Please arrive 10 minutes prior to departure which will provide us an opportunity to greet you and accompany you to your vessel.
Safety is our number one priority; COVID guidelines are in place.
More to know:
Food and beverages are available for purchase.
Please wear shoes with non-marking soles (deck shoes, tennis shoes, white-soled shoes). Avoid hard soles, high heels and black rubber-soled shoes.
All alcohol is required to be purchased in the office prior to departure. No red wines are available.
Please NO spray tanning products as these products can stain the boat.
Smoking of any substance is not allowed on board.
No pets on board.
Adventure Tips
Arrive Early for Boarding
Arrive at least 15 minutes before your scheduled departure to meet the crew and get safety briefings.
Bring Sun Protection
Florida sun can be intense on the open water—wear sunscreen, sunglasses, and a hat for protection.
Stay Hydrated
Pack water or ask if beverages are provided to stay hydrated during the sail.
Motion Sickness Preparedness
If you’re prone to seasickness, consider taking medication before boarding as the bay can have mild waves.
Local Insights
Wildlife
- Atlantic bottlenose dolphins
- Ospreys
History
St. Augustine was founded in 1565 as the oldest European-established settlement in what is now the continental U.S., with the bayfront playing a crucial role in its defense and commerce.
Conservation
Efforts are underway to protect Matanzas Bay’s water quality and native habitats, ensuring sustainable recreation and wildlife preservation.
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Adventure Hotspots in St. Augustine
Frequently Asked Questions
Recommended Gear
Light Jacket or Windbreaker
Protects against the breeze on open water, especially in cooler months.
spring;summer;fall;winter specific
Sunscreen
Crucial for preventing sunburn while exposed to direct sunlight on the bay.
spring;summer;fall;winter specific
Polarized Sunglasses
Helps reduce water glare and improves visual comfort on deck.
spring;summer;fall;winter specific
Camera or Smartphone
Capture historic landmarks, wildlife, and cloudscapes from unique vantage points on the sail.