2 hours - Private Day Sail along Historic St Augustine Bayfront
Pick your date
Highlighted days have spots open. Grey days are sold out or not running.
September 2026
Loading live availability
Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 20 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is 2 hours - Private Day Sail along Historic St Augustine Bayfront worth booking?
2 hours - Private Day Sail along Historic St Augustine Bayfront is a 2-hour experience in St Augustine, United States, from $795 per person. It scores 60 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 20 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 60 / 100
- Rating
- 5/5 (20)
- Duration
- 2 hours
- From
- $795 per person
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 pas
What you get
About this experience
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.
What's included
Included
- Bottled water
- On-board restrooms
- Yacht Captain
Not included
- Gratuities
What you'll see and do
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!
5 minutes here
Vilano Beach
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.
Pass by without stopping
Anastasia State Park
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.
Pass by without stopping
St. Augustine Lighthouse & Maritime Museum
As we move into the Matanzas River we will be close enough to capture some great photos of St Augustine Lighthouse in the distance.
Pass by without stopping
National Shrine Of Our Lady Of La Leche At Mission Nombre De Dios
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
Pass by without stopping
Castillo de San Marcos National Monument
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.
Pass by without stopping
Bridge of Lions
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.
Pass by without stopping
Where it starts and ends
Meeting point
St Augustine
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
No pickup: everyone meets at the start point.
Ends at
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.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- St. Augustine Sailing Enterprises
Know before you go
- Infants and small children can ride in a pram or stroller
- Suitable for all physical fitness levels
Photos
What travelers are saying
Outty’s summary of the themes that recur across 20 traveler reviews. Written by us, not quoted from reviewers.
Photo opportunities
3 mentionsThe views and photo stops come up again and again.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Traveler reviews
20 verified traveler reviews for 2 hours - Private Day Sail along Historic St Augustine Bayfront. Ratings and reviews provided by Viator and Tripadvisor.
Sunset Wine Tasting
Great experience. Great views. Great food. Great wine. Great staff. Great fellowship, Salute to Captain Kevin . We’d definitely do it again.
Response from the operator: Thank you so much for the great review. We look forward to seeing you out on the water again soon.
via Tripadvisor
Champagne dreams and relaxing atmosphere
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.
Response from the operator: 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!
via Tripadvisor
Take me away!!
Captain Daniel was great! He was very friendly & knowledgeable! The views were beautiful, wind perfect, & the weather was great!!
Response from the operator: 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.
via Tripadvisor
St Augustine Sailing great idea for a work team experience
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!!
Response from the operator: 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.
via Tripadvisor
Best day ever!!!
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.
Response from the operator: 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. 🌟⛵❤️
via Tripadvisor
Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 7
- Verdict
- Worth a Look
Why this scores 60
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
2 hours - Private Day Sail along Historic St Augustine Bayfront: questions travelers ask
Practical detail on this experience, plus the wider planning questions for St Augustine.
How much does 2 hours - Private Day Sail along Historic St Augustine Bayfront cost?
+
Prices start at $795 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in St Augustine usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does 2 hours - Private Day Sail along Historic St Augustine Bayfront take?
+
Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in St Augustine is not rushed.
Is 2 hours - Private Day Sail along Historic St Augustine Bayfront worth it?
+
It holds an Outty Ranking of 60 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 20 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in St Augustine, and how flexible the cancellation terms are.
Can I cancel or reschedule 2 hours - Private Day Sail along Historic St Augustine Bayfront?
+
Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is 2 hours - Private Day Sail along Historic St Augustine Bayfront suitable for kids and families?
+
Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book 2 hours - Private Day Sail along Historic St Augustine Bayfront?
+
Around 7 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in St Augustine can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
+
Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in St Augustine and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does 2 hours - Private Day Sail along Historic St Augustine Bayfront start and how do I get there?
+
The exact meeting point and directions are on your voucher once you book, and they sit in central St Augustine within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in St Augustine?
+
St Augustine is walkable history: Castillo de San Marcos, Spanish quarter walking tours, trolley loops, lighthouse climbs and some of the best-attended ghost tours in the country. Guide storytelling quality is the main variable. On Outty we rank every St Augustine experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Medieval Torture Museum with Ghost Hunting and Tiny Art Gallery, St. Augustine's Wine, Cocktail and Food Experience, Dolphin and Wildlife Adventure of St. Augustine. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit St Augustine?
+
February to May and September to November. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in St Augustine?
+
Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
+
Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
Ready to lock in your spot?
Pick a date, choose your group, and see the exact price for 2 hours - Private Day Sail along Historic St Augustine Bayfront.
Pick your date
