Sunset sailing in st augusitne with st augusitne sailing aboard wind dancer our luxury sailing catamran Lagoon 40


At St. Augustine Sailing, we specialize in crafting afternoon and evening captain-chartered sailing trips tailored for couples, families, or small groups seeking a slice of paradise on the open sea. But what sets our sunset cruises apart from the rest? It’s the magic of twilight, the allure of the unknown as day transitions into night, and the sheer beauty of witnessing the sun’s descent mirrored in the gentle waves below.

As the oldest continuously inhabited city in the United States, St. Augustine boasts a rich tapestry of historic landmarks, charming cobblestone streets, and breathtaking coastal views. It’s no wonder it is the perfect backdrop for a sunset cruise. It’s a chance to experience the city’s allure from a new perspective. Whether you’re seeking a romantic escapade with your significant other or a memorable outing with friends and family, our sunset cruises offer an experience like no other.

sunset sailing in st augustine sailing charter on our luxury sailing catamaran with st augustine sailing


Unlike daytime sailing excursions, where the sun hangs high in the sky, a sunset cruise offers a unique ambiance that is both serene and romantic.

Picture yourself on the deck of one of our luxury sailboats, the gentle sway of the boat beneath you as you glide effortlessly through the tranquil waters of St. Augustine. Now a fiery orb on the horizon, the sun paints the sky with orange, pink, and purple hues, creating a warm glow over the landscape. It’s a scene from a postcard, a moment frozen in time where nature’s beauty takes center stage.

But it’s not just the breathtaking scenery that makes a sunset cruise so magical—it’s the intangible sense of tranquility and romance that permeates the air. As daylight fades and evening sets in, there’s a quietude that envelops passengers, a feeling of being removed from the hustle of everyday life. It’s a chance to disconnect, to savor the present moment, and to revel in the simple joy of being with loved ones as the world slows down around you.


For those seeking a truly personalized and intimate sunset sailing experience, our private sunset charters offer the epitome of luxury and exclusivity. Departing from Camachee Cove Yacht Harbor, our private sunset sails invite you and your companions aboard a lavish sailboat for a two-hour journey along the historic bayfront of St. Augustine.

As you step aboard our meticulously maintained vessel, you’ll be greeted by our professional crew, dedicated to ensuring that every moment of your sailing adventure is extraordinary. Feel the wind in your hair and the ocean breeze caress your skin as you set sail into the golden hour, with the sun casting its warm glow over the architectural wonders of downtown St. Augustine.

From the vantage point of our comfortable sailboats, passengers are treated to a front-row seat to St. Augustine’s most iconic landmarks. As the sun sets in the west, casting its warm glow over the horizon, the city’s skyline comes alive with the silhouette of the Castillo de San Marcos. This centuries-old fortress stands as a symbol of St. Augustine’s storied past. Nearby, the Bridge of Lions stretches gracefully across the Matanzas River, its elegant arches illuminated by the fading light.

Throughout your voyage, our professional crew will be on hand to attend to your every need, ensuring that you and your guests have an unforgettable experience on the water. Indulge in cocktails and appetizers as you toast to the beauty of the setting sun and the memories being made aboard our luxury sailboat.

Our private sunset charters are fully customizable, allowing you to tailor the experience to suit your preferences and desires. Whether you’re celebrating a special occasion with a romantic evening for two or hosting a gathering of friends and family, our private charters provide the perfect setting for an unforgettable sunset sailing adventure.

Sunset sailing in st augustine with St Augustine Sailing


Our shared sunset sailing charters offer an intimate and communal experience like no other. These two-hour small group sails provide the perfect opportunity to connect with like-minded individuals while basking in the beauty of the setting sun.

One of the highlights of our shared sunset charters is the opportunity to take in iconic landmarks like the Bridge of Lions, the Castillo de San Marcos, the Great Cross, and the St. Augustine Lighthouse. Whether you’re a history buff eager to learn about St. Augustine’s storied past or simply seeking a breathtaking backdrop for your sunset photos, our shared charters offer the perfect blend of sightseeing and relaxation.

It’s important to note that our shared sunset charters require a minimum of two guests to depart, ensuring that each voyage is a shared experience for all on board. From solo travelers to couples and small groups, our shared charters offer the perfect balance of camaraderie and intimacy against the backdrop of a stunning St. Augustine sunset.


At St. Augustine Sailing, we pride ourselves on offering a sailing experience unlike any other. Our impressive fleet of sailboats, ranging from 21 to 45 feet long, ensures that every voyage is tailored to meet our guests’ preferences and desires. Each vessel boasts modern amenities, comfortable seating, and panoramic views of the stunning St. Augustine coastline.

Whether you’re on board for a private sunset charter or joining a small group for a shared sailing adventure, our dedicated captains and crew will treat you to the highest level of service and hospitality. With years of experience navigating the waters of St. Augustine, our captains are experts in their craft, guiding you on a journey of discovery as you explore the city’s historic landmarks and natural beauty.

But it’s not just the sailing experience that sets us apart—it’s the attention to detail and personalized touch we bring to every voyage. From the moment you step aboard, our crew is committed to ensuring that your sunset sailing adventure exceeds your expectations in every way. Whether serving up your favorite cocktail, sharing fascinating stories about St. Augustine’s history, or simply providing a friendly smile and warm hospitality, we go above and beyond to help make memories that will last a lifetime.

Book your sunset sailing adventure with St. Augustine Sailing today and embark on a voyage of discovery along the historic bayfront of one of America’s most charming cities. With our impressive fleet, dedicated crew, and unparalleled service, we guarantee that your sunset cruise will be an experience you’ll never forget.

Reserve your sailing adventure with St. Augustine Sailing. Choose from private or shared excursions.
St Augustine Sailing - Women on the Water - Girls night - Sip & Sail - Fun on the water - Sunset cruise
Culinary Offerings - Dinner Cruise - Brunch on the water - Sailing with dinner - Date Night - Unique dinner plans - Breakfast on a yacht - Dinner on a yacht - Sunset cruise - 4 course meal - Private Chef - St Augustine Sailing


Booking Information and Guidelines

Embarking on a sunset sailing adventure with St. Augustine Sailing is simple and hassle-free. To ensure a smooth and enjoyable experience, here’s everything you need to know about booking your sunset charter:

  1. Convenient Booking: Booking your sunset sailing charter is easy and convenient. Visit our website or give us a call to reserve your spot aboard one of our sailboats. Our friendly staff is standing by to assist you with any questions and help you plan the perfect sailing excursion.
  2. Location and Departure: Our sunset charters depart from Camachee Cove Yacht Harbor at 3076 Harbor Drive in St. Augustine. Upon arrival, you’ll find convenient and free parking at the marina, allowing you to park your vehicle easily before boarding your vessel.
  3. Arrival Time: We ask that guests arrive at least 15 minutes before departure. This will allow our crew ample time to greet you, accompany you to your vessel, and ensure you have everything you need for a memorable sailing experience.
  4. Safety First: Safety is our priority. Rest assured that our vessels are meticulously maintained, and our captains and crew are highly trained professionals with years of experience on the water. Before setting sail, our crew will provide a brief safety orientation to familiarize you with the boat’s layout and the necessary safety procedures.
  5. What to Wear: For your comfort and safety, we recommend wearing shoes with non-marking soles, such as deck shoes, tennis shoes, or white-soled shoes. Please avoid hard soles, high heels, and black rubber-soled shoes, as these can cause damage to the deck surface. Additionally, we ask that guests refrain from wearing spray tanning products, as these can stain the boat.
  6. Food and Beverages: Food and beverages are available for purchase aboard our sunset charters. Indulge in cocktails, wine, and appetizers as you soak in the sights and sounds of St. Augustine’s historic bayfront. All alcohol must be purchased in the office prior to departure, and no red wines are available.
  7. Prohibited Items: To ensure the safety and comfort of all passengers, we ask that guests refrain from smoking any substance while aboard our vessels. We kindly request that no pets be brought on board, as they pose a risk to other passengers and crew members.


         Raise your sails, set your course, and let the adventure begin. We’ll see you on the water!