A Guide to St. Augustine: The Oldest City in the US

By: Angie Orth

May 27, 2014

St. Augustine – about 45 minutes from Jacksonville – is known for being the oldest city in the US, but with that title comes the inevitable tacky tourist trap attractions. Take a look at our guide to St. Augustine for the sites that are really worth seeing.

St Augustine Beach | Jacksonville

St. Augustine is known as the First Coast because the Spanish settled here in the 1500s, making these shores the nation’s first European settlement © Rhea C

The North Florida region is colloquially referred to as The First Coast because St. Augustine is the oldest continually occupied European city in the United States. 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, an old Spanish fort still stands as a reminder of the early days of European colonialism in the Americas.

In the late 1800s, business magnate Henry Flagler, a partner of John D. Rockefeller’s, began to buy up railroads in Florida, bringing his wealthy northern friends down to experience the pleasant winter weather. Flagler’s construction projects signalled the beginning of Florida’s march toward tourism dominance.

St. Augustine Gate | Florida

The gates of St. George Street welcome visitors into the old city © PseudoDude

Over the years, St. Augustine changed hands from Spanish to British and back again, but today the city retains a decisively old-world Spanish colonial feel. While most of the original structures from the Spanish colonial settlement are long gone, the layout still reflects the original plan. The old city’s main buildings were constructed around Plaza de la Constitucion, now recognized as the oldest public park in the U.S. St. Augustine’s streets fan out from the plaza in a grid with St. George Street serving as the historic epicentre of town today. Its cobblestone path is lined with architectural curiosities from various historic eras. The Oldest Wooden Schoolhouse in the U.S. is one such point of interest, and this unimposing, 200-year-old cedar home is open for tours today.

Downtown, St Augustine | Florida

Downtown St Augustine is popular with walkers looking to take in the local scenery © Antoine Gady

St. George Street is restricted to pedestrians only, so it’s one of the best paths in town for a stroll. During the day, souvenir shops attract tourists and it’s a great place to grab a bite to eat. At night, tapas joints and wine bars fill up quickly with revellers. 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 conquistador from colonial times.

Castillo de San Marcos | St Augustine

Construction on the Castillo de San Marcos began in 1672, more than 100 years after St. Augustine’s official founding © Doug Kerr

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 was completed in 1696 on this fort, with its thick coquina walls and protective moat. Possession of the fort has changed peacefully six times throughout its history which now finds its place as part of the National Park system.

St. Augustine Alligator Farm | Florida

The St. Augustine Alligator Farm Zoological Park is the best place to see Florida’s native reptiles © Rachel Kramer

St. Augustine’s claim to fame is its historic ties (the oldest city in the US tagline), but there are some touristy attractions that are still worth seeing. It’s said that Ponce de Leon discovered the Fountain of Youth here, and those who can stomach the sulphurous smell are welcome to take a drink. Across the ornate Bridge of Lions is the St. Augustine Alligator Farm, home to hundreds of Florida’s reptiles and Crocodile Crossing, a zipline obstacle course that winds through the park and zips directly over the animals’ habitats. And there’s no better place in the U.S. to take those old-fashioned costume photos than St. Augustine.

Historic hotels and quaint B&Bs are the jewels in the Old City’s crown, so make time to visit one of the oldest hotels in the U.S., the Casa Monica, built in 1888 in St Augustine’s historic quarter. Dignitaries like Archbishop Desmond Tutu and the King and Queen of Spain have stayed here in the Moorish Revival and Spanish Baroque Revival-style hotel, which complements the colonial vibe.

St. Augustine Lighthouse | Florida

The St. Augustine Lighthouse is a local landmark © Doug Kerr

The St. Francis Inn is another historic place to rest your head, located on the corner of St. George Street and St. Francis Street. The property was built sometime around 1791, making it one of the oldest standing structures in the city. It’s filled with antiques and offers a shady courtyard for lolling about on a warm afternoon. The inn is on the National Register of Historic Places, and many guests have reported having encounters with friendly ghosts in some of the rooms.

Header photo: The St. Augustine Lighthouse © Doug Kerr

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Have you visited any of these historic St. Augustine spots? Where’s your favourite place to stay in the oldest city in the US? Share your thoughts with us below.

Written by Angie Orth


Angie Orth

Angie wears many hats; social media consultant, project-based publicist, travel blogger at, freelance journalist, big sister and adventurer. A Gator grad born and raised in Jacksonville, Fla., Angie spent the past two years traveling the world solo and writing about it in magazines and on her blog.

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