When I visit a new place for the first time, I find it difficult to relax when I feel lost. The place often feels big and overwhelming, and I’ll get this nagging suspicion that I’m missing out on something important. So for me, I want to know what there is to see, and where it is located in relation to me, my hotel, and any potential dining establishments. So that’s why I believe that to truly appreciate St. Augustine, it’s a good idea to wrap your wits around this little town, because it’s loaded with gems you could easily miss. And that would be really too sad, because there’s so much worth seeing.
To simplify this process, I recommend first buying a ticket to the Old Town Trolley Tours, settling down in the very last seat, and doing the full driving tour at least once all the way through. The tickets are about $20 each, however, they are good for three full days, and there are a dozen places where you can get on or off, so you can park your car and leave it for a few days and actually see St. Augustine in all her splendor!
You don’t, of course, have to take the trolley tour. This just happens to be how Grant and I saw St. Augustine the first time we ever visited, and I’m so so so grateful that we opted to see it this way. We took the whole tour, then got off the trolley at the next place we wanted to see. I never felt disoriented, and I had my bearings like someone who knew the town. This made for a relaxing and organized method of sight seeing * happy sigh * We did that for two full days, getting off the trolley here, climbing back on there. We walked a lot, but we also got to see more of St. Augustine than we would have otherwise, and because of the tour guide’s narrative of each little spot, we already knew a little about it when we visited. By the end of the second day, I could have given the tour (not really, but I felt that comfortable and confident). Another point to consider is that there are also places that aren’t really comfortable walking distance from the Historic District proper (like the Old Jail, The Fountain of Youth, etc). These are clear across town, so the trolley tour is a quick and easy way to get to those attractions without missing anything.
It has a number of other advantages as well:
- You’ll get to hear a detailed (though very mildly fabricated) history tour of St. Augustine. This is excellent because St. Augustine happens to have a rich and fascinating history that is a key ingredient in what makes it such a cool place to visit.
- In a little over two hours, you’ll get to orient yourself with the layout of St. Augustine visually. They’ll give you a map, but seeing all the actual landmarks in person, along with the map is perfect.
- After you’ve done the whole trolley tour, you’ll know what is where, and you can plan which places to see and when. Then you can disembark at the nearest trolley stop, and start enjoying the sights up close and personal.
- If you get tired of walking at any time, you can just mosey up to the nearest trolley stop, and in the next 15 minutes, a trolley will pull up and rescue you (unless it’s after hours and the trolley isn’t running, of course).
If you want to orient yourself quickly, and familiarize yourself with what this town has to offer, this is perfect! So there you have it. My advice to first time visitors of St. Augustine.
Savings Tip:
The St. George Inn is a great place to stay. It’s clean and well managed and right off the main walking street (St. George Street), and they usually have a special where you can get 2 FREE trolley tickets, free parking during your stay, and a free continental breakfast included in your room rate (which is really reasonable, by the way). We’ve stayed there a few times, and enjoyed it, the rooms were pretty comfortable.


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