With its mix of historic buildings, fun events and old-world charm, St. Augustine is a great destination for a day trip. It’s so jam-packed with things to see and do, however, that you might want to stretch your visit out to two or three days. The Ancient City or Old City, as it is nicknamed, is steeped in culture and history. It’s also just a fun place to spend a few free days. From quaint shops to fascinating, historic streets, St. Augustine has it all.
St. Augustine is the oldest European settlement in the United States. In a country where most of the cities are relatively young, it is an especially exciting place to visit. Florida was claimed for Spain by Juan Ponce de Leon in 1513. St. Augustine was officially founded by Pedro Menendez de Aviles in 1565. It has been inhabited ever since, and it’s waiting for you to stop by and explore it.
One of the best things about visiting St. Augustine is simply roaming its winding, historic streets. With that in mind, you should plan your visit for a time when the weather will be fairly nice. To put it mildly, St. Augustine can be scorching hot and oppressively humid in the summer. Daily thunderstorms are also the norm between June and September, when St. Augustine gets most of its annual 50 inches of rain. To walk the streets in comfort, try to plan your day trip for the fall, winter or spring.
Walking is the preferred way to take in the sights of St. Augustine, but there are a few other fun options for getting around as well. Horse-drawn coaches are available, and they are perfect for couples who want to make the most of the city’s romantic side. There are also trams that offer narrated tours of the city. Hop on one of them upon arriving to enjoy a nice, relaxing introduction to the city.
Some of the best events in St. Augustine happen during times of more moderate weather. The Rhythm & Ribs Festival, which combines fantastic barbecue and amazing music, takes place in March. The Holiday Regatta of Lights, which features lighted boats that travel across the St. Augustine Bay, happens in December. One perk to visiting St. Augustine in the summer is that you’ll be able to check out the annual Concerts in the Plaza series, which features free concerts on Thursdays throughout the season.
As far as seeing the sights goes, you have a dizzying array of choices in St. Augustine. Make sure to take a long, leisurely stroll along St. George Street during your visit. It is studded with charming boutiques, cozy restaurants, lovely art galleries and many unique shops. Of course for history buffs there’s the fort, Castillo de San Marcos. But try to visit as many of the following attractions as possible while spending time in St. Augustine too:
There are plenty of hotels in the area, but if I had to suggest one it would be the Casa Monica. I attended a wedding there once, and also did a weekend trip with my wife there. It’s a beautiful historic hotel, but has all the amenities you’d expect from the finer hotels in the world. Also, if you have a chance try the restaurant there called 95 Cordova.
St. Augustine will show you a whole new side of the state of Florida. It serves as a reminder of the state’s long, impressive history. The beach is right there too, so you can include some fun in the sun while you’re there as well.




When you get tired of walking, the scenic cruise (harbor tour) is a great way to spend a relaxing hour or so. Highly recommended!
I have not received any emails from you since March 2012. I love St. Augustine and plan to look into their retirement communities on my next trip to Florida.
Do you have any comments about the areas of florida where you buy the house but rent the land?