Top St Augustine Sailing Trips

Easy, fun beautiful sunset! I recommend this cruise to anyone well worth the price! Thank you for a great experience!

Great experience! Beautiful views of sunset behind the cross and lighthouse! Drinks and snacks included.

Enjoyed the cool tunes and cool breeze. Live music was great.

Great experience. Great views. Great food. Great wine. Great staff. Great fellowship, Salute to Captain Kevin . We’d definitely do it again.

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!

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.

Awesome staff and comfortable boat. The band was very good as well. An amazing experience all around. Highly recommend.

Donna and Chris were very knowledgeable and made our experience very pleasant. We enjoyed the spacious sailboat and our view of the lights was great.

Such a beautiful way to see the lights, the captain was super knowledgeable and gave us history on the city.

This was our second time to take a cruise with the St. Augustine Sailing company. We were on their beautiful Catamaran Vessel, which held 10 of us for this evening sail. I spent most of the ride in the front of the ship next to the Trampoline's, watching the water and the shoreline. Our entire party agreed that this was the highlight of our visit to the Festival of Lights.

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.

It was great time. The crew and band were exceptional.

Had a great time. Beautiful sunset and the music was great. The crew was amazing too. I would definitely recommend this to anyone who wants to have a great experience. Next time we are in St Augustine we will definitely be doing this again. Thanks

Such a great time on the Fury! We did a sunset cruise and enjoyed Night of Lights from the water. The crew was friendly and the band was great! Free drinks and snacks too!

This is my second trip on this boat and it was amazing. The captain and crew are super friendly and make sure your trip is enjoyable. I will always look to use them when visiting the area

Chris and Rose Ann were super hosts and well-prepared at navigating the catamaran when the dense fog rolled in! The vessel was very comfortable, clean and safe. Would go out with them again.