Top St Augustine Cruises & Sailing

Discover a new perspective on St. Augustine—and enjoy a relaxing trip out on the water—on this sightseeing boat tour. Pick from multiple start times, head to the marina, and hop aboard. See highlights like the Bridge of Lions, Castillo de San Marcos National Monument, and National Shrine of Our Lady of La Leche, and learn the stories behind the sights from your captain’s narration.

Cruise St. Augustine’s intracoastal waterway at sunset on this BYOB boat trip. Admire sights including the Bridge of Lions from the water at the most scenic time of day—sundown. Watch for dolphins and other marine life in the wild, hear tales about the city you may otherwise miss, and enjoy your preferred drinks as you sail and sightsee.

Cruise through St. Augustine’s scenic waterways on Fury’s Historic Landmark Boat Tour, where history, wildlife, and coastal scenery come together. Keep an eye out for playful dolphins, one of the highlights of the experience, as you enjoy 360° views of iconic landmarks like the Castillo de San Marcos and the St. Augustine Lighthouse & Maritime Museum. Choose a daytime narrated cruise or a romantic Champagne Sunset Cruise while your captain shares engaging stories spanning more than 450 years of St. Augustine’s rich history and points out native birds and other local wildlife along the way. Includes soda and water on all cruises, plus a complimentary champagne toast on the sunset tour. Perfect for families, couples, and groups.

Experience St. Augustine at golden hour on a sunset boat tour that combines waterfront views with light historical commentary. Cruising along the city’s shoreline offers a clear vantage point of notable landmarks while avoiding downtown traffic and crowds. The relaxed pace makes it easy to enjoy changing sky colors and local wildlife activity, creating a calm way to end the day on the water.

See St. Augustine from a new perspective with this leisurely sunset cruise. Climb aboard a boat for a scenic cruise including views of Castillo de San Marcos National Monument, the Bridge of Lions, and the St. Augustine Lighthouse. Sip beer or wine from the on-board bar with the Osprey, 21 and older option, or select the Island Breeze option for a family-friendly experience.

Sail along St. Augustine’s picturesque coastline—and indulge in a number of generous wine samples—during this two-in-one tour. Make your own way to the dock, hop aboard the pontoon boat, and get comfortable: as you set off, you’ll see landmarks like the Castillo de San Marcos, the Bridge of Lions, and more. You’ll also taste six different wines, and will have access to the on-board bar.

Sail through the historic harbors near Vilano Beach, as we seek out some of Saint Augustine’s most charming residents, the local dolphin population. We’ll view local bottle-nose dolphins as they frolic, feed, and engage in their natural behaviors. Guests will enjoy unobstructed views of the nation’s oldest city from the perfect vantage point, on the water. Our state-of-the-art catamaran provides 360-degree views, as guests enjoy complimentary sodas, water, beer and wine. This adventure is perfect for cosmopolitans and nature enthusiasts alike, seamlessly blending the historical allure of Saint Augustine with mother nature’s natural wonders.

Experience St. Augustine from the water on a private boat tour for up to six passengers. Cruise past the city’s historic waterfront with a dedicated captain who manages navigation while you relax and enjoy the views. Choose a daytime outing or plan around sunset for softer light and cooler temperatures, making this a flexible and intimate way to experience the city.

St. Augustine is one of the oldest cities in the United States and is a spectacular sight when viewed from the water. Get a glimpse of the city’s historic district and surrounding area during this sunset boat tour. You’ll cruise around the banks of downtown St. Augustine, gazing at sites like the Bridge of Lions and the Castillo de San Marcos National Monument. You’ll also venture into the St. Augustine Inlet and see St. Augustine Lighthouse & Maritime Museum.

As the oldest continuously occupied colonial settlement in the United States, St. Augustine has a wealth of history within its city limits. See both historical sites and natural landscapes while on this shared sailing cruise. Climb aboard a luxury yacht and sail down the Tolomato River and Matanzas River. This small-group sailing tour passes by the St. Augustine Lighthouse and Bridge of Lions, as well as showcases spectacular sunset views.

Sunset is one the most beautiful times of day and many people like to take cruises to see sights from the water when the sun goes down. Kick up the fun with this St. Augustine Sunset Booze Cruise that allows you to see the sights at sunset and enjoy some drinks on the water, too. This cruise has room for up to 24 passengers and takes place in a unique cycle boat.

This boat tour takes you onto the waters of St. Augustine in search of pods of bottlenose dolphins. As you explore, learn about local history and dolphins' biology and behavior from the expert crew, who know just where to find these mammals as well as other marine life such as turtles, manatee, osprey, and pelicans.

As the sun dips below the horizon and darkness cloaks the ancient city of St. Augustine, the bayfront tells a different story—one of restless spirits, eerie legends, and the lingering echoes of centuries past. Join us on our Haunted History Cruise, where spooky tales and history comes alive on the water. Led by our captivating guides, you’ll cruise along the Matanzas Bay and hear chilling tales tied to America’s oldest city. From the haunted lighthouse to the ghostly shores of the Castillo, this journey is steeped in spine-tingling lore. What you should know: This cruise is geared towards adults and teens, 13 and up.

St. Augustine’s Nights of Lights festival is among the historic city’s most celebrated events—but you can only get partial views while walking with the crowds on land. This evening boat tour makes the most of the scene, catching the lights and their twinkling reflections on the waterfront. And with a guide onboard, you’ll get fascinating insights you wouldn’t find on your own.

Enjoy a private kayaking adventure in St. Augustine and spot incredible local wildlife. As you paddle through the waterways led by your guide, look for dolphins, manatees, sea turtles, bald eagles, and more. Stop on a beach for natural beauty and more wildlife like conchs and starfish. Learn about St. Augustine history and wildlife along the way on this memorable experience.

Experience the magic of St. Augustine's Nights of Lights with Old Town Party Boat! Glide along the scenic waterways of the nation's oldest city while surrounded by dazzling holiday lights with your favorite drink in hand! We will be partying, dancing, singing & making memories while cruising past historic landmarks, beautifully adorned with twinkling lights, creating a festive atmosphere. Don't forget your camera to capture the enchanting moments! THIS IS A PARTY BOAT - EXPECT A PARTY! All tours are BYOB - Bring your own booze and food with you! AGE REQUIREMENT: 18 YEARS OR OLDER

Experience the Nights of Lights in St. Augustine from the water on this festive catamaran cruise. Choose between a narrated sunset option with historical context or a non-narrated viewing cruise focused on the illuminated skyline. Passing landmarks such as Castillo de San Marcos, this experience offers a unique way to view the city’s renowned Christmas lights with clear vantage points along the bayfront.

Escape the crowds with a Nights of Lights sailing tour aboard a comfortable yacht in St. Augustine. Unlike larger boat tours, this sailing experience offers an intimate, relaxed way to enjoy the city's famous festive light display from the water. Guided by a captain, take in the illuminated waterfront from carefully chosen vantage points for a more luxurious, personal sightseeing experience.

During St. Augustine’s Nights of Lights festival, the city is bathed in sparkling light. Choose the Sunset Tour to watch the sun set over the cityscape and see St. Augustine light up against the night sky, or the Evening Tour to enjoy the full nighttime display. Both tours offer live music and complimentary drinks, including beer, wine, margaritas, and hot chocolate, along with snacks, holiday cookies, and festive 3-D glasses that enhance the lights.

Explore St. Augustine’s Bay Front from the water on this private 2-hour cruise aboard a luxury sailing yacht with space for up to six passengers. With a USCG-licensed captain at the helm, sail along the historic bay front. Look for wildlife, including dolphins, and admire the historic sites. Relax onboard, learn about sailing, or even take the helm.

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting that allows guests to fully immerse in the beauty of the holiday lights without the crowds or noise of typical boat tours. Our yachts offer a more personalized, relaxed atmosphere with comfortable seating, and the option to book private charters. You’ll also be guided by experienced USCG captains who know the waters and the best vantage points to view the city’s spectacular light display. Whether you’re celebrating a special occasion or seeking a peaceful, romantic evening, our tailored sailing experience ensures you enjoy the Nights of Lights in comfort and style.