A Trip to the Oldest City – Saint Augustine, Florida


Saint Augustine, Florida.  The oldest city in the United States. Founded in 1565 by Spanish explorer Pedro Menéndez after defeating the native Seminoles and stealing their land, the city once served as a seaport as well as the foothold on colonization of the land mass that we now call the United States. Today it is a quaint tourist town boasting a wide variety of shops, historical attractions and scenic walks that seem like something from a movie set.

While it is a much less popular Florida destination than Miami, Fort Lauderdale or Daytona Beach, Saint Augustine hosts history, culture, shopping and a beautiful beach, all perfect for the Florida traveler who wants a change of scenery and access to corny war re-enactments. Located less than an hour south of Jacksonville, getting there from the Jacksonville airport is easiest by rental car, and for lodging there is a plethora of small hotels and charming bed and breakfasts scattered within the small city.

The old town is shaped by the intracoastal waterway, with beautiful boats filling up the marina. The Castillo de San Marcos, a historic Spanish fort sits on the waterfront and is available to tour, providing a glimpse into the history of the founding of the city as well as ceremonies of shooting off cannons and re-enactments.


A nice thing about the town is that it really can be experienced in one day, as long as you’re okay with walking a lot. The old city is very pedestrian friendly and is a beautiful place to walk in. Saint Augustine is a great place to stop in for a day if other spots in Florida are taking precedent on a vacation.


Restaurant Recommendations:

For an awesome happy hour, check out A1A Aleworks. They feature brews from their own brewery as well as many other local and imported beers. They have amazing appetizers on their happy hour menu, the blue crab and artichoke dip being a favorite amongst me and my friends who went two day in a row.

Catch 27 is an amazing local place that is small and serves up a great menu of different seafood items. I would definitely eat there again, and it is very reasonably priced



The Oldest Schoolhouse in the US








Other recommendations:
Kilwins: Get chocolate here. They have an amazing selection of fudge, truffles, caramel apples and other sweets

Stogies: A cool local bar that offers a free house cigar with any house pour. Yes, I did try to smoke a cigar and I quit after about three puffs. YEEUCKKK.

Bath Junkie: A haven for people who love customized beauty products and rad smells. Pick your product, scent and color and have it all whipped together in an awesome combination. Kind of expensive but their shea butter lotion makes your skin smooth as a baby’s ass.

Also check out TripAdvisor for more recommendations. I have never stayed in a hotel in St. Augustine, but there are a ton of cute ones to choose from.

Things I would skip:

Alligator Farm – unless you’re really into gators, this place is just a zoo for reptiles that stinks and is expensive.

Potter’s Wax Museum – Not worth the money. It’s cool for about five minutes and then it’s over and who really needs to see a wax figurine of the whole cast of Seinfeld?


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