Top St Augustine Private and Luxury

Bring your sense of adventure, and up to 6 of your closest friends for a private tour that is second to none. Explore themes like Haunted History, Spanish Colonial, Flagler Era & Gilded Age, Civil Rights or just tell your first rate guide your personal interests to create a truly unique experience. The most luxurious and comprehensive way to see the Oldest City.

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.

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.

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.

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.

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.

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.

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.

History buffs will love this unique historical walking tour through St. Augustine’s historic district. Your guide will cover the history of the city from its founding all the way up through the early 1900s. The tour covers nearly two-miles of ground, taking you from the Castillo de San Marcos National Monument to Flagler College and the Tolomato Cemetery. Bring comfortable shoes, bottled water, and a thirst for knowledge.

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.

Make the most of an evening in St. Augustine during “Blood on the Cobblestones,” a true crime pub crawl. Discover dark chapters of St. Augustine’s past, such as the oldest unsolved murder in the state of Florida. At each of the bars, you’ll hear stories of murder and will be guided through the scenes of five unforgettable crimes.

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.

Learn more about one of the oldest cities in the US while enjoying a frightfully good time on a family-friendly ghost tour of St. Augustine. Combine visits to spooky sites with light-hearted fun and spine-tingling tales. Your costumed guide takes you to cemeteries, the ground of the Old Fort, and other haunted locations to discover the little-known legends that you wouldn’t learn any other way.

See the streets of St. Augustine is a spooky new way on this evening ghost walking tour. As one of the oldest cities in the United States, St. Augustine has collected plenty of creepy legends and lore across the centuries. Hear about some of the city's most chilling past events, all while following your guide straight to its historic highlights.

Take your knowledge of St. Augustine’s history to a supernatural level when you join this small group guided ghost tour around the Ancient City. Instead of walking through the historic streets, you’ll hop on a golf cart with an expert guide in search of paranormal sights. Learn about the dark history of St. Augustine when visiting sites like Flagler College and the Castillo de San Marcos.

See St. Augustine’s historic sites and lively streets from the water on this sightseeing boat tour. You’ll meet your captain at the Vilano Public Pier then ride off into the waters surrounding the city for a unique sightseeing tour that combines dolphin searching with a lesson on the history and ecology of the area. Evening tours include a viewing of the nightly sunset. This is a family-friendly experience passing by the Bridge of Lions, St. Augustine Inlet, and more.

Explore the darker side of St. Augustine on a golf cart ghost tour that combines historic storytelling with modern comfort. Travel between haunted locations efficiently in a low-speed vehicle equipped with immersive lighting and sound. Cover more ground than walking tours while your guide shares documented history and reported encounters, offering a deeper and more atmospheric look at the city’s supernatural past.

Explore St. Augustine’s beautiful Intracoastal Waterway on your private floating tiki boat! This BYOB cruise is the perfect way to relax, take in scenic waterfront views, spot local dolphins, and enjoy good times with friends or family. Whether you’re seeking a romantic sunset cruise, a lively booze cruise, or a private charter, this fun and customizable experience is your ticket to the best of St. Augustine by water. What to Expect: Scenic boat cruise along St. Augustine’s Intracoastal Waterway and Matanzas Bay Floating tiki boat atmosphere BYOB booze cruise with cooler and ice provided Private or shared options available Dolphin watching and wildlife spotting opportunities Romantic sunset cruises and island-hopping options

Make the most of your day in St Augustine and save money in the process with a package that includes admission to three historic attractions plus a hop-on hop-off trolley tour of the city. Visit the Old Jail, the St Augustine History Museum and the Oldest Store Museum Experience, plus dozens of other points of interest among the city’s top attractions.

Please support small businesses and look us up on the web to book directly. Just do a search for: Pineapple Ride and Tour ***Nights Of Lights tours are available directly on our website ONLY*** See Saint Augustine like you never have before on one of Pineapple Ride and Tour's Electric Vehicle. Our Historical Tours are guided by only the best and most informative local guides. Join us to see an hour or more of St. Augustine’s most incredible views and historical landmarks. Our tour is informative, comfortable, and is a great way to get to know where everything is, making your stay easier and more relaxing. We will take the time to get to know you and share our knowledge of our beautiful little town. Leave our tour with a new understanding of Saint Augustine and its history. We also offer FREE PARKING at our location if you book a tour, and we have a very nice waiting area by the edge of the San Sebastian River, that is both accommodating and scenic.

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.

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.