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St. Augustine, A City Under Siege - Historical Re-enactments And Festivals Visitors Love

Castillo de San Marcos

Castillo de San Marcos bell tower. Credit: Alberto Fernandez Fernandez

About the Author

Robb Zerr

Writer

Robb Zerr has been an award-winning writer for the last 22 years. He has lived life among the palm trees in Florida for the last six years, crisscrossing the state as a travel writer, tourist and bon vivant. He lives beachside on the Treasure Coast.

Founded in 1565, St. Augustine is the oldest city in the country.

If you're looking for the oldest city in America, you have to go farther south than Virginia. A lot farther south. Founded in 1565, St. Augustine was established by the Spanish 41 years before Jamestown, making it the oldest city in the country.

Located on the East Coast of Florida just south of Jacksonville, this town still features many of the early buildings, including the massive Castillo de San Marcos, which still guards the seaside approaches of the city from invaders.

For those who love history, St. Augustine will not disappoint you. The main street of the town, St. George, retains a lot of its original character, thanks to ongoing preservation efforts. You can even visit the nation's oldest schoolhouse along this picturesque lane where old and new mixes with ease.

Small wonder why the city has been under siege for much of its history, right up until today. But if you see soldiers taking positions and pirates coming down the street, don't be too alarmed. Historical re-enactments of key battles are part of the city's charm and celebration of its history.

The two major re-enactments, Searle's Raid and Drake's Raid, are well worth attending, especially if you have children. The battles are very realistic, with cannon and rifle fire and swordfights from one end of town to the other.

Searle's Raid of 1668 - Early March

The biggest re-enactment happens in early March. It marks the successful attack by buccaneers on the city in 1668. Led by Capt. Robert Searle, the buccaneers sailed into Matanzas Bay aboard two captured vessels on the evening of May 28. The ships were expected, but the pirates weren't. As the city slept 100 buccaneers poured ashore, seizing the residents as they emerged half dressed from their homes. Within 20 hours the buccaneers had sacked the town and killed 60 of its townsfolk.

Re-enactors recreate this famous Sack of St. Augustine, retracing the steps of the battle as it entered the city's plaza and made its way back down the streets of St. Augustine. Supported by men with pikes, the buccaneers had the Spanish outgunned with their modern flintlocks, which could outshoot the Spanish matchlocks three to one.

If you come to town to see the raid, head to the Fountain of Youth Park first. This is where the buccaneers are mustering before the battle. Here, you can see what life was like in the 1660s. The encampment offers a fairly accurate re-creation of the times, complete with period cooking techniques, medical equipment, food and drink, attire, and of course, weapons. The re-enactors in camp will be happy to teach you all about the times and show their displays of period ware.

Later in the day, the battle begins. You'll want to head into town before the battle. You can't follow the buccaneers on the march - they ride into town in very unauthentic trams. Even re-enactors get tired feet.

It's not hard to follow the battle itself. Just listen for the gunfire in town. Be sure your camera has lots of fresh batteries, as there are plenty of photo opportunities, both in the camp and in the streets.

Drake's Raid of 1586 - Early June

While history books of yore portrayed Sir Francis Drake as a brave explorer, the people of St. Augustine thought him a pirate of the worst sort. On June 8, 1586. Drake attacked the city with 23 ships and 2,000 English soldiers. He drove the Spanish from the town, then sacked and burned it to the ground.

The re-enactment of the battle begins in Fountain of Youth Park where soldiers perform drills in preparation of protecting the city from Drake's men. Visitors to the park can also enjoy historic encampments, displays of period weapons and interpretive presentations about the life and times of the middle of the 16th Century.

As evening approaches, the battle begins in the city and in the plaza. Soldiers in period garb and using weapons appropriate to the era battle for supremacy. Cannon blaze in the night, as do matchlock muskets. It is a very exciting time to visit St. Augustine, as the 400 year-old buildings and the re-enactors combine to send you back in time. You'll feel as if you're right there, watching Drake sack and burn St. Augustine.

The best vantage points are at the beginning of the battle, which starts at the Santa Domingo redoubt on Orange Street. It then continues to the City Gate, then south on St. George to the Plaza de la Constitucion.

As with Searle's Raid, the battle on the streets is free to watch. The Fountain of Youth Park has a small admission fee, which includes the encampments and a chance to drink from the fabled Fountain of Youth and perhaps gain eternal life. At least that's the legend.

Don't miss...

While you're waiting for the battles to begin be sure to visit the Castillo de San Marcos. The raids on St. Augustine by Drake and Searle are the reason the fort was built. It was constructed out of a material called "coquina", which translates literally as little shells and is composed of hardened, ancient shells. The coquina was quarried on Anastasia Island and brought to the construction site. The fort took 23 years to construct and was finished in 1695. It is said to be quite haunted, having been featured on several ghost-hunting shows. So if you feel is if someone is looking over your shoulder, you may be right. Especially in the prison.

For more information on the re-enactments, contact the St. Augustine, Ponte Vedra & The Beaches Visitors and Convention Bureau at (800) 653-2489 or visit their website at www.getaway4florida.com.

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