Drake’s Raid on St. Augustine was a military event during the Anglo-Spanish War in which the Spanish settlement of St.
Augustine (Spanish: San Agustín) was captured in a small fight and burned by an English expedition fleet led by Francis Drake. This was part of Francis Drake’s Great Expedition and was his last engagement on the Spanish Main before Drake headed north to the Roanoke Colony. The expedition also forced the Spanish to abandon any settlements and forts in present-day South Carolina. You and your family are invited to join the living historians of the Men of Menendez and Drake’s Men on the first Saturday in June each year for this educational and entertaining day of history. Check our calendar for the specific date.
On June 6th, 1586 twenty-three ships approached the harbor of the Spanish colonial city of St. Augustine with 2000 Englishmen under the
command of Sir Francis Drake. A day after making sight of the harbor, 1000 of these men, led by Captain Christopher Carlile, would land on Anastasia Island to mount cannons opposite the Spanish wooden fort and begin to duel with the Spanish forces there. Three hundred Spanish would abandon the fort during the night and with daylight approaching on the morning on the 8th the English crossed Matanzas Bay, taking the fortification and proceeding to drive the Spanish rear guard from the city of St. Augustine. Click here to read an actual account of a witness to the original event.
Understanding the military “uniforms” of St. Augustine 1586
There was little difference in the general appearance of St. Augustine’s Spaniards and Drake’s men who sacked the city. The
town’s elite would favor military styles (St. Augustine was a presidio or garrison town). During this period, there were few uniform regulations for Spanish troops in the New World – dress was left to the individual unit commanders. Consequently, there was little uniformity and Spain’s American garrisons tended to wear whatever clothing was available. The apparel of any slaves would have been much like poor Spaniards. Native Americans (Timucuan, Apalachee, Guale, etc.) in the town would dress the same as the Spaniards; rural “pagan” natives (not following the Spanish Catholic teachings) would be in traditional garb – loincloths, tattooed, painted, etc.
The reliving of Sir Francis Drake’s Raid on old San Agustín begins on Friday, May 13th and 14th at the Oldest House Museum ( the Gonzalez-Alvarez House) located at 14 St. Francis St. In St. Augustine from 10am to 5pm.
During the day on Saturday please feel free to visit with our living history interpreters in their 16th century-style military encampment as you tour the our encampment as local historians, play host to drills, demonstrations and living history interpretation from 10:00 AM to 5:00 PM.
Saturday evening, the recreation of the sacking and burning of the town will commence at 7:00 PM in the old city beginning at the Old City Gates (including the Santa Domingo Redoubt on Orange Street.) A skirmish breaks out as the Spanish soldatos at the redoubt spot Drake’s men coming ashore. The Spanish soldados and the St. Augustine citizens flee with Drake’s soldiers in pursuit. Skirmishes continue as the Spanish move south on St. George Street towards the plaza continually trying to hold off the ever-advancing English soldiers. The final battle between the Spanish soldados and Drake’s men takes place at the Government House. This military display is intended to symbolically commemorate the temporary abandonment of the city of St. Augustine by Spanish colonial forces. After the town was looted and burned by Drake’s men, the Spanish returned to rebuild upon the same streets you walk on today!
Never been in a living history event before? We can fix that! Join us and watch, join us and learn or join us and enjoy a day reliving history at
Drake’s Raid.
Drake’s Raid is made possible in part by a grant from the St. Johns County Tourism and Development Council.
Other Local History to Visit While You Are Here
- Colonial Quarter Museum- Journey back in time through the history of St. Augustine. From our distinctive 35-foot watch tower and colonial buildings to shops and dining.
- Fountain of Youth- We invite you to visit us for a fascinating, informative, entertaining tour of Ponce de Leon’s Fountain of Youth Archaeological Park, the original site of the Nation’s oldest city. Located in the area first explored by Juan Ponce de Leon in 1513.
- Castillo de San Marcos National Monument, St. Augustine, FL- A monument not only of stone and mortar but of human determination and endurance, the Castillo de San Marcos symbolizes the clash between cultures which ultimately resulted in our uniquely unified nation.
- Ft. Matanzas National Monument, St. Augustine Beach, FL- Fort Matanzas guarded St. Augustine’s southern river approach. The colonial wars are over, but the monument is still protecting—not just the historic fort, but also the wild barrier island and wildlife.
- Ft. Mose State Historical Park, St. Augustine, FL- Historic site of a free-slave settlement, preserving history and natural beauty.
- St. Augustine Lighthouse and Maritime Museum- The Museum today serves 225,000 visitors each year. The Interpretive Division provides docent-led guided tours that are free with the cost of admission. This includes a tour of artifact conservation areas featuring artifacts from historic shipwrecks. Ship modeling, Heritage Boat Building and interactive exhibitions use visual, audio, tactile, and kinesthetic learning to share information with everyone
Things to Do
- Old Town Trolley- Trolley Routes & Stops with a lot of helpful information on St. Augustine's Points of Interest, Shopping & Entertainment, Restaurants & Bars and much more!
- Florida's Historic Coast- A Comprehensive Community Calendar
- The Spanish Bakery- A local baker's blog and home of many tasty treats. Right off St. George Street.
- ST. JOHNS CO. CULTURAL COUNCIL- HistoricCoastCulture.com is a one-stop source for information about all the performances, venues, exhibitions, and community events that are happening year-round in the St. Augustine area.
- visitstaugustine.com- Visitors will find an array of attractions in the nation's oldest city. From living history museums like the Castillo de San Marcos to Gilded-Age hotels, swashbuckling adventures and specialized tours in the air, on the sea, and in the heart of the historic district, Saint Augustine has it all!
- Lightner Museum- Lightner Museum is housed in the former Alcazar Hotel built in 1888 by Henry Flagler. Today it is home to one of the finest collections of fine and decorative 19th century art in the country. The Museum is open to the public seven days a week and features self-guided tours, tours by reservation for adults and children, and demonstrations of antique mechanical musical instruments.
- St. Augustine Pirate and Treasure Museum- The Museum offers an exciting and educational museum experience that transports you and your family back in time over 300 years to Port Royal, Jamaica, at the height of the Golden Age of Piracy.
- Classic Car Museum of St. Augustine- The Classic Car Museum of St Augustine was created to help bring memories back to life as only Classic Cars can do. Visitors are provided with the opportunity to experience cars from the 1800s to modern day sports cars.
