Want to visit the oldest city in the USA? We’ve partnered with Florida native and travel expert Angie Orth from AngieAway.com to find out the basics of planning a visit to St. Augustine.

Flager College in St. Augustine, Florida

Did you ever wonder why North Florida is known as “the First Coast?” Most folks think of Jamestown or Plymouth as the beginning of the European settlement of North America, but Spanish St. Augustine predated the English, Dutch and French in the New World by quite a while. First explored by Juan Ponce de Leon in 1513, the city was eventually settled in 1565 under Admiral Pedro Menéndez de Avilés. Five hundred years later, the Spanish fort stands as a reminder of European colonialism in the Americas.

Over the years, St. Augustine flip-flopped from Spanish to British control (a common occurrence in forts and settlements in the coastal South) but the vibe today is old-world Spanish colonial. Most structures from the Spanish settlement are long gone, destroyed by hurricanes and hundreds of years, but the city’s layout still reflects the original plan. Centered around the Plaza de la Constitución (the oldest public park in the country), St. Augustine’s narrow streets fan out from the plaza in a grid. Here are some of my favorite sites to see as you walk in the footsteps of history!

St. George Street in St. Augustine, Florida

St. George Street

St. George Street is a pedestrian only thoroughfare, so it’s the perfect place to start exploring. During the day, souvenir shops attract hordes of visitors and it’s a great place to grab a bite to eat. At night, tapas joints and wine bars fill up quickly with both locals and travelers. Outdoor seating is common and live music can be heard up and down the narrow alleyways branching off the main road. In the dark, it’s not too difficult to imagine carousing here as a rum-drenched pirate.

Hop-on, Hop-Off Trolley

The quickest way to get to know St. Augustine is a hop-on, hop-off trolley tour. A lively guide shares tales of the city’s history on the adventure, which features 19 stops you can check out at your leisure. The tour is an hour if you just ride without hopping off, but you won’t want to miss the chance to see some of St. Augustine’s top attractions like the Old Jail, Flagler College and the San Sebastian Winery.

Castillo de San Marcos - St. Augustine, Florida - Angie Away

Castillo de San Marcos

Across from St. George Street along the shore of Matanzas Bay is the Castillo de San Marcos, the most enduring landmark from the Spanish occupation. Construction of this coquina-walled fort was completed in 1696. Possession of the fort has changed peacefully six times throughout its history which is now a part of the National Parks system.

The Fountain of Youth

It’s said that Ponce de Leon came to North Florida in search of the Fountain of Youth, and if you can stomach the sulfurous smell, you can actually take a sip of it. Touristy? You bet! But still something you can only do in St. Augustine.

Bridge of Lions in St. Augustine, Florida

The Alligator Farm

Cross the ornate Bridge of Lions from the Old City to the St. Augustine Alligator Farm on Anastasia Island. The world famous attraction is home to hundreds of reptiles and Crocodile Crossing, a zip-line obstacle course that winds through the park. There’s nothing like flying directly over a pool of hungry alligators to make you say, “Only in Florida!”

Historic Hotels and B&Bs

Deciding where to stay in St. Augustine can be the hardest part of planning a visit. Convenient chain hotel or quaint bed and breakfast? Historic mansion near St. George Street or coastal retreat near the striped lighthouse on the Atlantic Ocean? When I go, I like to do both — a few days in the Old City followed by a few days of chill beach time. History and nature all wrapped up in one vacation!

Check out my blog post for more ideas on where to stay when you visit St. Augustine. And if you’ve been, share your favorites in the comments below!

St. Augustine Lighthouse

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