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 HFM 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.

The reliving of Sir Francis Drake’s Raid on old San Agustín begins  on Saturday  at the Colonial Quarter Living History Museum, located at 43 St. George St. with a 16th century-style military encampment.

During the day on Saturday,  our local historians, play host to drills, demonstrations and living history interpretation from 10:00 AM to 5:00 PM. The reenactment of the sacking and burning of the town will commence Saturday evening at 7:00 PM in the old city, beginning at the Old City Gates ( including the Santa Domingo Redoubt on Orange St.) As Drake’s men come ashore, a skirmish breaks out with the Spanish Saldados.  The Spanish saldados  and the St. Augustine citizens flee with Drake’s men in pursuit. Skirmishes continue south on St. George Street  towards the Plaza de la Constitucion. The final battle takes place in front of the Governor’s 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! This event is brought to you by the Men of Menendez and Drake’s Men with the assistance of the St. John’s County Tourist Development Council.

The Historic Florida Militia would like to thank the Colonial Quarter Living History Museum for hosting this St. Augustine historical event.

Participation Rules & Information

Online Registration takes place in the month prior to the event.

If you are planning to tent, we must know the footprint of your tent and/or fly prior to the event. All tents and arrival date must be registered by May 25th.  (Space is limitied). Any tent not preregistered will not be permitted to set up until all registered tents are set up.

Three Ways to preregister your tent:                                                    

  1. Online registration form.                                                                            
  2. Call Jeff Johnson at 904-534-6168                                                              
  3. PM Sharon De Jorge on Drake’s Men/Men of Menendez FB page

You can also be able to register on site when you arrive. You must be a member of an HFM unit and pay annual membership dues , your participation fee will be $10 per person. There will be a $20 fee per person if you are not a current member of Historic Florida Militia. These will be collected when you arrive. This is extremely important as only members of the company are covered for insurance purposes. Please ensure that we at least have a good e-mail address and phone number for you on the registration form.

Encampment Rules:
Drake’s Raid/Men of Menéndez Rules will be posted at the Registrar tent
• All vehicles must be removed from the encampment immediately after unloading.
• Appropriate 16th century period tentage is required.
• Tents/flys must be PRE-REGISTERED before May 25.

Encampment Setup

The setup and arrival time for the event will be after 3:00pm Thursday  and all day Friday at the Colonial Quarter. If you arrive before 5pm on Thursday or Friday, please use the Trolley pull off across from the Castillo. The gate will be open for you to enter the encampment area temporarily to unload your equipment. Vehicles are not permitted to remain in the encampment site during Visitor’s hours at the Colonial Quarter. (Parking is located at Historic Downtown Parking Facility, 1 Cordova St., St. Augustine Fl. 32084)

If you arrive After 5:00pm on Thursday or Friday, you many enter into the encampment site via the gate located in the Trolley pull off, across from the Castillo. Participants are asked to move your vehicles asap after unloading.

No vehicles will be allowed in camp on Saturday. After the battle on Saturday night, if you need to break down your camp and leave before Sunday, you must see an event organizer for help with this. The purpose behind these rules are to keep the camping area as “period” as possible. We feel that this enhances everyone’s enjoyment while at the event. Cars will be allowed into camp Sunday morning after 6 am.

Camp Regulations

Property Etiquette:
• When attending an event, please remember: YOU ARE A GUEST ON PRIVATE PROPERTY.
• Respect the property and their guests.
• Any problem and/or question regarding a property issue, guest or customer needs to be reported to the event’s chain of command first.

Behavior in Camp:
• The inappropriate public display of alcoholic consumption is not allowed.
• Please refrain from drinking alcoholic beverages during Colonial Quarter operating hours.
• Do not carry around with any alcoholic beverages in the encampment during the Colonial Quarter operating hours.
• No open container alcohol beverages allowed on St. George Street.
• No underage consumption of alcohol is allowed.
• Unlawful use of drugs is STRICTLY prohibited.
• Violation of the above specified rules can be cause for immediate ejection from the event.
• No lewd behavior– grounds for possible immediate ejection
• No smoking in designated black powder areas.
• Only period correct pipes, cigars, or other smoking forms are allowed.

Proper Period Dress:
• All members must be dressed in proper period encampment clothing.
• No polyester clothing, striped stockings, wristwatches, etc., will be allowed.
• No modern eyeglasses will be allowed. Please try to obtain contacts, “period” eyeglass
frames, or go without if possible. Most optometrists or eyeglass frame shops can fit lenses of your prescription in “period” frames.
• Women portraying men can use the 10 foot rule. No make-up allowed.
• No make-up, nail polish and/or non period-correct jewelry is allowed.
• No modern tennis shoes or modern sunglasses are allowed.
• Anyone not dressed in proper period encampment clothing will not be allowed to participate in any camp activities or be in the camp proper. This is a public event…. “When in doubt, don’t.”

Overnight Camping:
• Overnight camping is available for participants 18 years of age and older WHO DISPLAY PROPER AND APPROPRIATE CONDUCT.
• Anyone under 18 years of age must stay with his or her parent or guardian.

Drake’s Raid Battle RULES:
You MUST BE REGISTERED to participate in the battle. No one will be allowed to participate in the battle if not registered prior to the battle.
• Appropriate period correct 16th century weapons will be required.
• No black powder weapons may be discharged in St. Augustine’s downtown area before or after the “Drake’s Raid” event.
• Please refrain from any overt visible cell phone use in front of the public both in camp and during Drake’s Raid on St. George Street.
• Do not touch tourists without their permission.
• Swords and knives must be sheathed in public, (unless you have permission from an event officer to have it unsheathed.)
• Anyone under 14-17 years of age must have a signed waiver or written consent from a parent or guardian to participate in the battle. See the registrar when registering for the event about the waiver.

Please do not use profanity or indulge in lewd behavior during business hours at the Colonial Quarter, the battle reenactment and/or when we are on the streets of downtown St Augustine,especially when there are visitors and children present. If you are unsure if a phrase or action is profane or lewd: don’t say or do it.

Food Schedule:                                                                                        
Thursday & Friday: Meals on your own
Saturday: Light breakfast will be available. Noon lunch will be provided. The Evening meal will be leftovers or meals on your own.
The Final Jollification of the Season will commence after the battle.

Due to the location of the Colonial Quarter, there is access to a variety of restaurants within walking distance of our encampment.

General Appearance, Guidelines and Suggestions

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.

Native Americans (e.9., Timucuan, Apalachee, Guale, etc.) in the town would dress the same as the Spaniards; rural, pagan natives would be in traditional garb – loincloths, tattooed, painted, etc. The apparel of slaves would be like poor Spaniards.

We are always looking for new recruits to portray townspeople, garrison soldiers and Native Americans. You need not be an historian, actor or military enthusiast to participate in our events. We do focus on accurate historical impression, using correct materials, styles and equipment. Members of Historic Florida Militia (as well as clothing and accessories) , are available to assist  you to participate in our events.

Registration Form

Please check back in May for Our Registration Form to Be Online

After Action Review

We will use both our Facebook page and direct email to solicit your impression and comments about all aspects of the event. We try to make it better every year. Half of grant from the TDC must go towards advertising.