Top St Augustine Private and Luxury

Enjoy a comfortable and flexible way to explore the best of St. Augustine on this narrated Old Town trolley tour. See dozens of points of interest, such as the Old Jail, Flagler College, and Spanish colonial neighborhoods. Along the way, discover more about America’s oldest city, founded in 1565, from your conductor, and listen as they share in-depth narration about St. Augustine's history.

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.

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.

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.

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.

Enjoy a 90-minute walking tour through the nation’s oldest city, exploring centuries of history, architecture, and hidden stories that shaped St. Augustine. From the Castillo de San Marcos to charming colonial streets, and the beautiful waterfront, this tour hits all the highlights—perfect for first-time visitors or anyone looking to truly understand the city. The beauty of a free walking tour is that you get to decide what it's worth to you personally. Your licensed local guides receive no salary of any kind other than what they receive from guests on a tip basis. If you have a group larger than 6, please contact us in advance to make sure we can accommodate.

The coastal town of St Augustine is renowned as the oldest European settlement in the United States. On this private tour, benefit from the undivided attention of your guide and enjoy a tour itinerary tailored to your group’s interests. Traveling by electric vehicle, visit areas normally only accessible on foot, stop at historic landmarks and churches.

Relax on a serene adults-only Sunset River Jazz Cruise along the historic St. Augustine bayfront. This two-hour journey features live jazz, artisanal charcuterie, and a complimentary glass of boutique wine while you watch the sunset over the water. Ideal for date nights or a calm evening with friends, this cruise offers comfortable seating and scenic views, perfect for conversation and unwinding. Enjoy the laid-back atmosphere as you take in the sights and sounds of the river, with wildlife like dolphins occasionally making an appearance. - 2-hour adults-only cruise starting at sunset - Live jazz band sets the mood for relaxation - Includes artisanal charcuterie and one complimentary glass of wine - Comfortable seating and scenic views, perfect for socializing

Discover St. Augustine's historical sites with ease, without the hassle of research or figuring out transport, during this private guided tour. Ride in a vintage vehicle with guides dressed in 1920s fashion as you cruise past landmarks such Castillo de San Marcos, Flagler College, and St. George Street in the historic district, while learning more about the sites than you would on your own.

Get close to the unique wildlife living just off the shores of St. Augustine during this on-water adventure tour. Choose between a kayak or a paddle board, slip on a life vest, and head out onto the water with a guide. As you paddle around the St. Augustine Lighthouse and Anastasia State Park, you may encounter dolphins, sea turtles, and the West Indian manatee.

St. Augustine’s original “frightseeing” tour provides an evening of fear and fun. Board Ghosts and Gravestones' Trolley of the Doomed for a spooky ride through St. Augustine's sinister past. Listen to stories of the ghosts and ghouls believed to still wander the town’s streets as you pass supposedly haunted hot spots, and visit Potter’s Wax Museum. Expect a tour so scary, it comes with a warning: not recommended for under-13s.

This relaxing cruise is great for nature lovers, families, or those who simply enjoy being out on the water. Cruise the Intracoastal Waterway—an inland waterway that runs parallel to the coastline—for a calm ride exploring St. Augustine’s estuaries. Keep your eyes peeled for marine life such as dolphins, manatees, sea turtles, pelicans, osprey, and spoonbill. Along the way, you’ll spot landmarks including the Bridge of Lions, Castillo de San Marcos, St. Augustine Lighthouse, and more.

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.

Discover the United States’ oldest city as you embark on a historic walking tour through St. Augustine. Join a small group and visit top landmarks such as the oldest masonry fort in the US, the oldest grid system, and Flagler College. While you explore, your guide sheds light on the tumultuous history of the 450-year-old city.

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.

See St. Augustine's key landmarks—and enjoy a one-of-a-kind, environmentally friendly way of traveling—on a small-group electric golf cart tour. Choose a convenient morning or afternoon tour time, meet your guide in the city center, and hop on board. See St. Augustine landmarks, including the Castillo de San Marcos, Tolomato Cemetery, and Mission Nombre de Dios, and learn all about the city’s centuries of history.

Experience St. Augustine from the water on a sightseeing cruise that combines local wildlife viewing with views of the city’s historic waterfront. Traveling by boat allows you to see key landmarks from a different perspective while avoiding crowded streets and walking routes. This relaxed cruise offers a steady pace and open views, making it an easy way to enjoy both nature and history in one outing.

Explore St. Augustine’s historic districts on a small-group tour designed to provide clear historical context without extensive walking. Traveling by low-speed vehicle, cover key landmarks efficiently while hearing structured commentary through a premium sound system. With pickup included and a maximum of seven guests, this tour offers a more personalized way to understand the city’s layered history in a compact timeframe.

Some claim St. Augustine is one of the oldest cities in the US, but unless you see its sights and hear its history, you may not understand or agree. This St. Augustine Boat and Golf Cart Combo Tour lets you see main landmarks of the city by both land and water, for a well-rounded introduction. First, go on a boat tour, and then cruise the city in a golf cart.

This food and wine tour offers an efficient way to explore St. Augustine’s culinary scene alongside its history. Guests benefit from guidance by a sommelier and historian, providing clear context behind each pairing and location. The electric cart format reduces walking and allows access to multiple stops with ease. With pre-selected tastings included, it delivers a curated experience combining dining, local insight, and convenient transport.

Take your knowledge of St. Augustine’s history to a supernatural level on this small group guided ghost tour. Instead of walking, hop on a golf cart with an expert guide to visit paranormal sites like Flagler College and the Castillo de San Marcos. The tour offers audio and written guides in multiple languages, making the dark history accessible to more visitors.

A delicious tour of America’s Oldest City awaits you on this chauffeured food and wine tour through St. Augustine. This auto-adventure whisks you through the streets of St. Augustine’s historic district in an open-air electric vehicle, stopping at some of the guide’s favorite dining venues. Local cuisine paired with tasty wines await your taste buds. As you ride along the streets, pass Flagler College, the Huguenot Cemetery and other historical landmarks.

If you’ve got an appetite for experiencing the best food and wine St. Augustine has to offer, then grab a bib and a comfortable pair of walking shoes for this unique foodie tour. Corks and Forks is a food and wine pairing tour that’ll introduce you to the tasty side of America’s Oldest City. Sample local cuisine and delicious wine while strolling through the Historic District.