I love planning trips. When I’m excited about an upcoming trip, I’ll often research it for weeks.

I tend to approach life as “a maximizer.” Basically, I try to get every last drop of beauty and value out of each experience. So, when I travel, I want to understand the local culture, discover the most interesting and unique attractions, and find a way to do the trip on a budget. This week, I’m planning our road trip to St. Augustine, the oldest city in the U.S. I’ve been there a few times–but usually just for a few hours at a time. It’s been a year and a half since I last passed through, and that was just for a quick dinner and a stroll down St. George Street. (The picture above is my only documentation of that evening.)

This time, we’re planning to stay in St. Augustine for a couple of nights. When I did my research, I found three attractions that made it to the top of my list.

1. Trolley Tour. I love riding around a city and getting a visual overview of its history, streets, and attractions. If it has a hop-on/hop-off option, I’ll usually ride the full tour once, making a mental note of the places that I want to explore later. St. Augustine has several trolley tours, and–as a maximizer–I’m hoping to find one that has a combination of the best deal, the most interesting stops, and at least one “included” attraction (such as free admission to a museum).

2. Tour of Flagler College. Some of my friends recommended this one. They said that Flagler College has a spectacular campus, one that’s definitely worth checking out. The college’s official website describes it as “one of the finest examples of Spanish Renaissance architecture.” It was once the grand Hotel Ponce de Leon, where people such as Mark Twain, Babe Ruth, and Teddy Roosevelt stayed. Then it was used as a training center for the Coast Guard during World War II.

3.Castillo de San Marcos. For a long time, I’ve assumed that the picture below was taken at the top of Castillo de San Marcos. My parents took me to St. Augustine when I was a teenager. (How high would you rate my sense of fashion in the mid-nineties?) I barely remember that experience, but I’ve associated this photo with my earliest memory of St. Augustine–even though it could have been from a visit to a different fort. It’s been almost two decades since then, so it seems like an appropriate time to go back and clarify that memory. When I’ve have the opportunity to relive a childhood adventure, I’ve enjoyed assembling a multi-layered collage of it in my mind. My earliest memories form the crayon marks and doodles in the background. Then my adult self glues its snapshots and descriptions to the foreground, which helps me to discover an overall theme: Nice Place, What I’d Do Differently, Great Times, Never Want to Go Back, or I’d Recommend It. The theme adds another level of meaning to the experience.

If we can, while we’re in St. Augustine, I’d also like to see the Oldest Wooden School House and the St. Augustine Pirate and Treasure Museum. They both sound fascinating. I know that we’ll have limited time and money (and museums are sometimes the most costly attractions), but I’ll be looking for coupons and two-for-one deals online.

If you’ve been to St. Augustine, what did you do while you were there? What was your favorite part of the trip?