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.
From the operator’s live schedule on Viator, checked Oct 9.
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.
Reviews collected by Viator and Tripadvisor
Excurgo comparison of 204 Viator tours, recalculated daily.
For a full refund, cancel at least 24 hours before the scheduled departure time.
2 hours - Private Day Sail along Historic St Augustine Bayfront lasts about 2 hours. The itinerary has 7 stops.
Prices start at $795 per person for this St Augustine experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
According to the operator’s current schedule, it runs every day, starting at 9:00 AM, 11:00 AM, 1:00 PM, and 3:00 PM.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
The meeting point is We are located inside Camachee Cove Yacht Harbor & Marina. As you turn into the marina, continue straight past the security guard building and we are the 5th structure on the right. Our office is located on the first floor of a two-story white building. Free parking is available. Hotel pickup is not part of this experience.
The experience is available in EN.
It is a private experience: only your party takes part. Up to 15 travellers can book together.
Infants and small children can ride in a pram or stroller
Yes, bookings are confirmed instantly.
Travellers rate it 5.0 out of 5 across 20 reviews on Viator and Tripadvisor; it is run by St. Augustine Sailing Enterprises.
Reviews collected by Viator and Tripadvisor
Great experience. Great views. Great food. Great wine. Great staff. Great fellowship, Salute to Captain Kevin . We’d definitely do it again.
Thank you so much for the great review. We look forward to seeing you out on the water again soon.
We took the wine pairing tour, which paired 7 dishes with wines from across the United States. Meals were elaborate and delish, every participant took at least one recipe home to try, and the wines are already in order. What a great way to experience St. Augustine from the water. The crew was attentive but let us be and the boat was clean and in great shape.
Thank you for the wonderful review! We’re so happy to hear you enjoyed the wine pairing tour and the chance to experience St. Augustine from the water. Our team loves creating menus that are both memorable and approachable, so hearing that guests left with favorite recipes — and wines already on order — absolutely makes our day! We’re also glad you appreciated the balance our crew strives for: attentive service while still allowing everyone to relax and enjoy the atmosphere at their own pace. Thank you as well for noticing the care we put into maintaining our vessels and creating a comfortable onboard experience. We truly appreciate you sailing with us and hope to welcome you back aboard again soon for another evening of great food, wine, and unforgettable views!
Captain Daniel was great! He was very friendly & knowledgeable! The views were beautiful, wind perfect, & the weather was great!!
Thank you again so much for the wonderful review. I will make sure to let Daniel know... we all try hard to make your experience the best it can be.
Captain Kevin and crew Vince were wonderful! They made the experience super fun - we went straight for the dolphins and got to watch them play. Even saw a giant sea turtle. From the reservation to the return every interaction was pleasant and professional. Highly recommend!!
Thank you so much! I will make sure to let the staff know. We all try very hard to have our guests have the best time ever. I am so happy that you saw dolphins and a turtle.
My husband and I celebrated our 25th anniversary with St Augustine Sailing. We sailed with Dale and couldn’t have asked for a better captain. He made us feel like our day was special and we couldn’t have asked for a better experience.
Thank you for letting us be part of such a special milestone! We're honored that you chose St. Augustine Sailing to celebrate your 25th anniversary. It’s wonderful to hear that Captain Dale made your day unforgettable and ensured you felt truly celebrated. Congratulations again on 25 years of love and adventure! We hope to welcome you back aboard for more cherished memories in the future. 🌟⛵❤️
We have taken a number of cruise experiences and this one stands out. the staff is very interactive and welcoming. at one point it turned into a photoshoot! the group was made to feel very special. It was great to see the sites of St. Augustine from the water side and the food was perfectly set for us. thank you.
Thank you so much!!! We hope to see you again!
Amazing time sailing! Enjoyed every minute. Our captain was friendly and made the whole experience wonderful for us. I would love to do it again.
We are so happy to hear you had a great time!!!
We had a magnificent experience, weather was awesome, boat was very clean, the business owner was very patient with us,allowed us to use the restroom before departure. Captain was so kind and very knowledgeable, I would like to go again soon, i would recommend them to all family and friends. They also respected the time frame. I love everything about this trip.
Thank you so much for your kind words! We are so happy you and your family had a great time. We hope to see you on the water again soo.
This was a lux and lovely experience. Loved seeing St. Augustine from the water and the team was very hands-on and welcoming. Rose Ann enhances the experience with her photo skills and story telling. Thank you.
Thank you so much Gustavo for your great review! We loved having you and your group with us aboard Wind Dancer. We are so happy that you liked the photos Rose Ann took and hearing all her stories about living and sailing aboard her own vessel. We look forward to seeing you out on the water again with St Augustine Sailing.
Peaceful morning sail and a beautiful add-on brunch. Communicative and easy to work with. Thanks Captain Chris!
Thank you for your lovely review! We’re so happy to hear you enjoyed a peaceful morning on the water along with the brunch add-on, it’s one of our favorite ways to start the day. We’re glad our team made everything easy and seamless for you, and we’ll be sure to pass along your thanks to Captain Chris. He does a wonderful job creating calm, enjoyable experiences aboard. Thank you for sailing with us, and we hope to welcome you back again soon for another beautiful day on the water.
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| 2 hours - Private Day Sail along Historic St Augustine Bayfront | 2 hours | 5.0 (20) | $795 | |
 Private Guided Historic Electric Cart Tour of St. Augustine | 1h 30min | 5.0 (1,238) | $200 | View |
 St. Augustine Live Music Sail with Drinks & Sunset Option | 1h 45min | 4.7 (417) | $66 | View |
 St. Augustine Dolphin Watch and Historical Harbor Sail | 1h 30min | 4.7 (93) | $39 | View |
 St. Augustine Hop-On Hop-Off Trolley Tour | 1h 30min | 4.5 (4,146) | $41 | View |
 St. Augustine Ghost Tour: A Ghostly Encounter | 1h 30min | 4.7 (2,486) | $30 | View |
 Medieval Torture Museum with Ghost Hunting and Tiny Art Gallery | 1–2 hours | 4.9 (2,429) | $25 | View |