St Augustine’s scenic bayfront and historic waterways make it an ideal spot for short, memorable boat tours. Unlike many destinations where a quick trip feels rushed, here you get a relaxed, intimate view of the city’s sights and wildlife.
We love the private sunset sail for its romantic vibe and personalized experience, and the day cruise for those wanting a laid-back exploration with a touch of adventure.
Both tours offer a chance to see St Augustine from the water—something that’s hard to beat when trying to understand why folks keep coming back.
If you’ve ever wondered about the city’s coastline or wanted a peaceful break from walking, these two options deliver.
For those seeking a quiet, scenic evening, the 2 hours – Private Sunset Sail along Historic Bay Front is a standout. But if you prefer a daytime adventure on a luxury yacht, the Private Day Sail along Historic St Augustine Bayfront offers a more relaxed, flexible experience. Both promise excellent views, wildlife spotting, and a chance to see the city from a whole new perspective.
1. 2 hours – Private Sunset Sail along Historic Bay Front
At number one on our list is the Private Sunset Sail—a perfect choice for couples, families, or small groups wanting a personal touch. This tour takes you out on a private vessel with a captain and crew, sailing along the historic bay front just as the sun dips below the horizon.
The itinerary includes stops at Porpoise Point, Vilano Beach, Anastasia State Park, and views of the Castillo de San Marcos and the Bridge of Lions.
What makes this tour stand out is its focus on wildlife, especially the chance to see porpoises and other marine life. The sunset timing means your views are at their best, with golden hues reflecting off the water. The private nature ensures a calm, intimate experience—ideal for celebrating a special occasion or just enjoying a peaceful evening.
Most reviews praise the captain’s experience and the personalized service, with one noting, “It was a wonderful first time on a sailboat.” The cost is $795 per group, which is fair considering the exclusivity.
Bottom line: This tour offers a beautiful, relaxed, and romantic way to see St Augustine’s waterways at sunset, with wildlife and landmarks in full view.
2. 2 hours – Private Day Sail along Historic St Augustine Bayfront
For a daytime experience, the Private Day Sail on a luxury yacht is hard to beat. This tour also lasts about two hours and caters to groups of up to six people. Setting out from Camachee Cove Yacht Harbor, you’ll glide along the Tolomato River and into the Matanzas River, passing along Vilano Beach and the Porpoise Point area, where wildlife sightings are common.
The highlight is the chance to see dolphins and the city’s iconic landmarks from the water, including the stunning St. Augustine Lighthouse.
What makes this tour appealing is the flexible, relaxed vibe. You’re not just a passenger—many guests take the opportunity to learn sailing skills or even take the helm. The captain, licensed by the US Coast Guard, ensures safety and fun, whether you want to relax or get involved. Guests rave about the “peaceful morning sail” and mention how easy it was to coordinate.
The cost is $795, which covers the entire group, offering good value given the private setting and luxury yacht experience.
Bottom line: If you’re after a tranquil, scenic cruise with the option to learn about sailing, this private day sail provides both relaxation and adventure for up to six people.
How to Choose
Choosing between these two great options depends on what you’re looking for. If a romantic sunset or evening cruise appeals more, go for the Private Sunset Sail. It’s perfect for photography, wildlife spotting at dusk, and enjoying a peaceful moment in a private setting.
On the other hand, if you prefer a daytime adventure with a bit of a hands-on experience, the Private Day Sail offers a flexible, luxurious cruise where you can relax, learn, or even take the helm.
Consider your budget, timing, and whether you want a romantic evening or a daytime escape. Both tours are private, so booking early is highly recommended, especially during busy season. Think about who’s coming with you—families, couples, or friends—and pick the experience that best suits your interests.
Final Thoughts
St Augustine’s waterways are a highlight, and these 2-hour boat tours provide a unique way to see the city’s iconic sights and wildlife from the water. For romantic evenings, the sunset sail offers a peaceful, scenic escape. For daytime exploration, the luxury yacht cruise combines comfort, adventure, and a chance to get involved.
Both options are excellent choices, especially if you’re short on time but want a meaningful experience. The private setting means you can tailor your trip to what matters most—whether it’s wildlife, landmarks, or simply unwinding on the water.
If you’re eager to enjoy these excursions, booking early will help ensure you get the time and date you want. With a little planning, your St Augustine water adventure is bound to be a highlight of your trip.