Enjoy a Luxurious Dinner Cruise in St. Augustine

St. Augustine is a destination known for its restaurants. In 2019, Southern Living named us the Best Food City in the South, and local favorites Collage, The Floridian, and Michael’s regularly show up in national “Best Of” lists. Obviously, we have great choices if you want a special occasion restaurant or an amazing dining spot by the water. But what if you’d like to dine on the water? Your best bet is a dinner cruise in St. Augustine.

Couple with fruit and wine on a sunset dinner cruise in St. Augustine

St. Augustine Dinner Cruise Options

That was a question we got recently from a guest. He was looking for a private dinner cruise in St. Augustine that would knock his girlfriend off her feet. We knew just the place to recommend—St. Augustine Sailing, which offers luxury chef-led dinner cruises through the Matanzas Bay at sunset. Trust us, these dinners are Over the Top. St. Augustine Sailing is located in the Camachee Cove Harbor, just at the base of the Usina Bridge. That’s the tall bridge that connects downtown St. Augustine to Vilano Beach. The Marina is a little over a mile from our beach cottages and a little over two miles from downtown. They have ample parking.

Seafood and rice dish

Mouthwatering Fresh Fare

St. Augustine Sailing also has ample choices for your luxury dinner! Choose from three different kitchen talents—Chef Wesley Nogueira, Executive Chef, Chef James W. Phelan, and Rose Ann Points, the amazing owner of St. Augustine Sailing and a great cook in her own right. Picture delicate hors d’oeuvres, rich soups and light salads, plus a mouth-watering entree like local fish, seared scallops, or pork tenderloin. Don’t forget dessert—there are wonderful options for your sweet tooth! I’m thinking about their chocolate lava cake right now!

Boats on the water in St. Augustine, Florida

Sail Off Into the Sunset

Sunset dinner cruises in St. Augustine are three hours long. Beer, wine, and other drinks can be bought through St. Augustine Sailing. The dining experience starts at $1,995 for two, which includes food, drinks, a private sailing yacht, and tips. We think it’s a great finishing touch to a St. Augustine proposal (maybe in our gazebo or on one of our decks?) that your S.O. will talk about for years. I mean, who wouldn’t want to start their lives together with a night of wonderful luxury?

Couple with champagne on a dinner cruise in St. Augustine

Do It Yourself

If that budget is a little high for you, there are other options. The Marina is just behind the Kingfish Grill, an excellent seafood and sushi restaurant by the water. Call in your order and pick it up on your way to the sailing office. We’re happy to lend you a picnic basket to help keep your food hot! In this case, you’d just have to book the private cruise for you and your honey (starting at $795 for two hours, and $995 for a catamaran) and grab dinner on the way there. Many of our restaurants in town offer meals to go as well—we’re happy to help you find the perfect fit for your magical night on the bay. Add a bottle of champagne (if you purchase our Marry Me Proposal Package, we provide a bottle of chilled bubbly!) and you are off for a night to remember.

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