2 hours - Shared Sunset Sail along Historic St Augustine Bayfront
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.8/5
Based on 8 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is 2 hours - Shared Sunset Sail along Historic St Augustine Bayfront worth booking?
2 hours - Shared Sunset Sail along Historic St Augustine Bayfront is a 2-hour experience in St Augustine, United States, from $199 per person. It scores 53 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4.8/5 rating across 8 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 53 / 100
- Rating
- 4.8/5 (8)
- Duration
- 2 hours
- From
- $199 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
- Yacht Captain
Not included
- Gratuities
- Alcoholic beverages
- Snacks
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.
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.
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
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
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.
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 6 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 8 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
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.
Small groups
3 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
8 verified traveler reviews for 2 hours - Shared Sunset Sail along Historic St Augustine Bayfront. Ratings and reviews provided by Viator and Tripadvisor.
Unforgettable Evening
I’ve toyed with many different ways to write this review; a way to fully articulate how amazing our evening was on St. Augustine Sailing. From the moment we arrived, the warmth radiated from Roseanne was like being greeted by your best friend. We were led to a beautiful vessel and assisted onto the deck by her crew, each person genuinely happy to welcome us aboard. The tables were set simply elegant, ready for what we anticipated to be a culinary delight. Pictures were taken, safety guidelines were given, the menu described, and we set sail! On this intimate cruise we celebrated and laughed, enjoyed five (plus a bonus) courses of a beautifully curated menu with exquisite wine pairings—each described and served with such joy for the occasion. The evening sky painted vivid shades of orange and violet, the sea lively with dolphins yet calm as we glided through the bay. Free to move about the ship between courses, Roseanne took many opportunities to photograph the evening, sharing yet another talent with us to commemorate such an event. As we were served each course, wine crisp and perfectly paired, we were able to enjoy conversations with the crew and take in the beautiful sights of St. Augustine’s coastline. Seeing the Ancient City from the water makes us love it on land even more! As dessert was served, we pulled back into port, mindful of the wind conditions—the crew keeping us safe and warm—the sun fully set for the evening. The magic of this extraordinary experience coming to an end as we disembarked; truly grateful for Roseanne and her crew for exemplary service, fabulous fare, beautiful sights, and a Birthday I will never forget. Some people want to cross items off a to-do list—to say they did it—while others want to savor each moment, knowing they are truly experiencing something special. We chose the latter and it was everything and more we had hoped for. Thank you St. Augustine Sailing!
Response from the operator: Thank you for such a beautifully written and heartfelt review. Reading your words truly means the world to all of us at St. Augustine Sailing. We are honored that you chose to celebrate such a special birthday with us, and even more grateful that the evening created memories you’ll carry with you for years to come. Roseanne and the crew work hard to create an experience that feels welcoming, intimate, and unforgettable, so hearing that you felt cared for from the moment you arrived is incredibly meaningful. From the cuisine and wine pairings to the dolphins, sunset skies, and peaceful sail through the bay, it sounds like Mother Nature and our crew came together perfectly for your evening aboard. Thank you as well for recognizing the little details (the hospitality, photography, conversation, safety, and atmosphere) that help make these cruises truly special. Your description captured exactly what we hope every guest experiences: not simply checking something off a list, but slowing down and savoring every moment. We are so grateful you sailed with us and hope to welcome you back aboard again soon for another unforgettable evening on the water.
via Tripadvisor
Most intimate experience in St Augustine
Amazing experience - captain was knowledgeable, so accommodating, and went out of his way to make the experience extra special. Sunset photos were the best we got on our trip, dolphin sightings were endless. Only thing missing was a little bit of wind lol.
Response from the operator: Thank you so much! We agree Sunset photos from the water are the best! It is always amazing to see dolphins... it never gets old no matter how many time you see them. We look forward to seeing you out again with us when there is a little more wind. Thank you again.
via Tripadvisor
A totally breathtaking and memorable experience!
Sailing the harbor as the sun set was truly remarkable. The natural scenery coupled with the Christmas holiday illumination of the St. Augustine seaport was breathtaking. Capt. Chris and 1st Mate David were truly sailing experts who both added jovial conversation, local history and a personal interest in our experience. This was an event that made our stay here most memorable!
Response from the operator: Thank you so much for your wonderful review! We're delighted that you had such a remarkable experience sailing at sunset in St. Augustine. It sounds like Capt. Chris and 1st Mate David made sure your journey was not only beautiful but also informative and enjoyable with their expertise and local insights. We're thrilled to have been a part of making your stay memorable, and we hope to welcome you back soon for more unforgettable moments on the water!
via Tripadvisor
Great experience!
Such a great experience! The sailing portion was exhilarating! What a great way to see coastline! Having the wine options was a nic way to relax as well! It was chilly but worth every minute. Highly recommend doing this tour!
Response from the operator: Thank you so much for your great review. We are so happy that you enjoyed your sail with St Augustine Sailing. Look forward to seeing you out on the water again.
via Tripadvisor
Good but average
Overall this was an average experience. It had great potential but lacked the hospitality side of the experience, which was unfortunate. When we arrived 30 minutes early, they rushed us on the boat which felt like we were late (we asked, we were not late) and took off without any instructions or offering us a chance to get food/drink/water. The cruise itself was pleasant and our captain was nice and informative. If the hospitality were better, I would give this a 5 star.
Response from the operator: Carly, I am so sorry that your experience fell short. We pride ourselves on customer service and I am truly sorry we fell short here. Thank you again for sailing with us and hope we see you again.
via Viator
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
- 3
- Verdict
- Worth a Look
Why this scores 53
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
2 hours - Shared Sunset 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 - Shared Sunset Sail along Historic St Augustine Bayfront cost?
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Prices start at $199 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 - Shared Sunset Sail along Historic St Augustine Bayfront take?
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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 - Shared Sunset Sail along Historic St Augustine Bayfront worth it?
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It holds an Outty Ranking of 53 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.8/5 across 8 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 - Shared Sunset Sail along Historic St Augustine Bayfront?
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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 - Shared Sunset Sail along Historic St Augustine Bayfront suitable for kids and families?
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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 - Shared Sunset Sail along Historic St Augustine Bayfront?
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Around 3 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?
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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 - Shared Sunset Sail along Historic St Augustine Bayfront start and how do I get there?
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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?
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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?
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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?
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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?
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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.
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