**IMPORTANT: If you are booking this tour after June 1st 2026, see Spyglass on this site to book our new improved experience** We take a unique approach to tours in St. Augustine, using the latest technology. Our certified guides offer the most experienced and entertaining historical narrative of the city of St. Augustine, locations of historic events and the citizens who helped create and maintain the oldest city in the nation. We will cover the founding of the city, the first Spanish period, the British Period, the second Spanish period, the American territorial period, and the Flagler Era /Gilded Age This is a walking tour which covers a 1.7-mile route over the 90 minutes of the experience. It takes place during the day in Florida, so plan accordingly. Wear comfortable walking shoes, bring water, sunscreen and maybe an umbrella as well. There will be restrooms available at the beginning, end, and at the midway point as well. This is the perfect tour for the history enthusiast!

Best first way to see St. Augustine. See the highlights of St. Augustine the easy way on a small group golf cart tour. The best first way to see St. Augustine is with Explore Tours and PickUps, especially if it’s your first time visiting. You’ll cover more ground than walking tours while enjoying a personal, guided experience through the nation’s oldest city. Perfect for couples, families, and anyone wanting a relaxed but informative overview before exploring on their own. Cruise through the historic district while learning the stories behind St. Augustine’s most important landmarks. Your guide shares history, local insight, and recommendations so you know exactly what to do after the tour. Many guests choose this as their first activity to get a feel for the city and often search for us again after to plan future visits or recommend us to friends.

Please support small businesses and consider booking us directly, just use a web search to find us: Pineapple Ride and Tour ***Nights Of Lights Tours are available on our website ONLY*** Our Historical Tour is informative, comfortable, and convenient. Our expert tour guides will take the time to get to know you and share many stories about the oldest continuously occupied european settlement in the continental United States. Our tours are conducted on an electric vehicle with open sides and seat up to 10 People. This is an excellent way to see where everything is, and to learn Saint Augustine's history in a fun and informative way. Three reasons to consider our tour: - FREE parking or get picked up anywhere downtown, Just call - We are pet friendly, all sizes and breeds welcome - This is THE MOST conveniently located and professional tour service available in Saint Augustine.

Best first way to see St. Augustine. See the highlights of St. Augustine the easy way on a small group golf cart tour. The best first way to see St. Augustine is with Explore Tours and PickUps, especially if it’s your first time visiting. You’ll cover more ground than walking tours while enjoying a personal, guided experience through the nation’s oldest city. Perfect for couples, families, and anyone wanting a relaxed but informative overview before exploring on their own. Cruise through the historic district while learning the stories behind St. Augustine’s most important landmarks. Your guide shares history, local insight, and recommendations so you know exactly what to do after the tour. Many guests choose this as their first activity to get a feel for the city and often search for us again after to plan future visits or recommend us to friends.

A golf cart tour is the best way to experience the entire downtown area and visit the sites on the north of the colonial city. Golf carts allows easy access to get off and take pictures; feel the breeze and provide uninterrupted views of the sites. For larger groups, please contact us.

Enjoy a leisurely walk through the ancient streets of the nation's oldest city. A more intimate and in-depth telling of the history of the people and events that led the city through the trials and tribulations of the past. Learn the complete history of our Oldest City, from its founding by the Spanish, through the various colonial periods, into the territorial period and statehood and finally into the revitalization of the Gilded Age Renaissance of the city as an exclusive tourist destination. Groups are kept small by design, tours are interactive, ask all the questions you would like, and hear the a complete history not just a few blurbs of stories as you pass by. Let us introduce you to the real history of the Nation's Oldest Continuously Occupied European Settlement, or as we say, the Oldest City.