2 hours - Private Day Sail along Historic St Augustine Bayfront


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Duration2 hours
Good To KnowE-voucher
13 reviews


We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory.
This 2-hour sail gives passengers a chance to make new memories on the sea. Our cruise is perfect for all water-lovers: families, couples, and friends. Some guests enjoy interacting with the USCG licensed Captain, learn a little about sailing, or take the helm. Others relax and enjoy the trip.
No matter your preference, this cruise will be a highlight of your vacation.


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!
As we slip away from the marina, we will be making way along Vilano Beach. Porpoise Point at Vilano Beach is a beautiful waterfront community and bounded by the intracoastal waterway. This area is known for seeing dolphins as the feed during tide change. As we sail by, it is almost certain you will see dolphins in this area.
Anastasia State Park is across the waterway from Vilano Beach, and you will be able to see the more northern park as we leave the Tolomato River and continue down the Matanzas River.
As we move into the Matanzas River we will be close enough to capture some great photos of St Augustine Lighthouse in the distance.
The Great Cross and also known the Mission Cross and the Beacon of Faith Cross is located on the grounds of the Nombre de Dios Mission. The Great Cross was erected in 1966 and stands 266 feet high. It is built of 70 tons of stainless-steel plates, packed with concrete in its lower third to prevent toppling by weather conditions.
The Great Cross stands tall as part of the backdrop and can be seen during the entire sailing experience
Built by the Spanish in St Augustine to defend Florida and the Atlantic trade route, Castillo de San Marcos National Monument preserves the oldest masonry fortification in the continental United States and interprets more than 450 years of cultural intersections.
The bridge gets its name from two white marble lion statues guarding the bridge on the west side. Completed in 1927, the Bridge was constructed during the extravagant land boom times in Florida. It was designed as a work of art as much as a transport for cars, connecting downtown St Augustine with Anastasia Island. A double-leaf bascule bridge, or drawbridge, it opens for boat traffic several times throughout the day.


Bottled water
On-board restrooms



Additional Information

  • Infants and small children can ride in a pram or stroller
  • Suitable for all physical fitness levels

Cancellation Policy

  • A full refund will apply if you cancel more than 24 hours before the activity start time.

  • No refund is possible if you cancel less than 24 hours before the activity start time.