Searle’s Raid for Participants

Searle’s Raid is an annual event that re-creates the famous bloody pirate raid on St. Augustine in 1668, takes place on the first Friday and Saturday of March. Join us in the reenactment of the “1668 Sack of St. Augustine” in St. Augustine Florida, our nations’ oldest city. During the day a 17th century-style military encampment will be open to the public at the Gonzalez-Alvarez House (The Oldest House Museum) located at 14 St. Francis St. and will play host to military drills, demonstrations and living history interpretation from 10:00 AM to 4:00 PM. The actual sacking and burning of the town will commence Saturday evening at 4:30 PM in the old city’ The actual route may vary depending upon city permits.

We are always looking for new recruits to portray townspeople, garrison soldiers, Native Americans, and buccaneers! Our focus is on an accurate historical impression, using correct materials, styles, and equipment. You need not be a historian, actor, or military enthusiast to participate. The “Sack of St. Augustine: Capt. Robert Searle’s Raid of 1668” is a historical reenactment sponsored by Searle’s Buccaneers and the Men of Menendez (members of the Florida Historic Militia), with the assistance of the St. John’s County Tourist Development Council and the St. Augustine Historical Society.

In 1655, Oliver Cromwell’s “Western Design” resulted in the capture of Spanish Jamaica, thus providing English freebooters with a safe base from which to plunder the Spanish Main. The “Golden Age of Piracy” had begun! In 1668, Captain Robert Searle and his privateers sailed from Jamaica to loot the silver ingots held in the royal coffers at St. Augustine. Under the cover of night, they slipped into the harbor and attacked the sleeping town, killing sixty people and pillaging government buildings, churches and homes. The devastation wrought by these bloodthirsty pirates prompted Spain’s Council of the Indies to issue money to build a massive stone fortress on Matanzas Bay to protect the city. The Castillo de San Marcos still stands as an enduring reminder of Florida’s exciting heritage!

The procession that commemorates the arrival of the raiding pirates and introduces this annual event will begin at the The Oldest House Museum at 4:30 p.m. on the first Friday of March and will proceed north on St. George Street to the Santo Domingo Redoubt on Orange Street. The Searle’s Sack encampment will take place on the first Saturday from 10 a.m. to 4 p.m. at the Oldest House Museum. The reenactment of the battle between the freebooters and the city’s Spanish defenders will take place in St. Augustine’s historic district at 4:30 p.m. on Saturday. The English brigade will head up St. George Street from the Plaza toward the city gates, and the battle will commence when the English try to invade the Spanish defenders who will be stationed at the Santo Domingo Redoubt off Orange Street across from Potter’s Wax Museum. Living history gets real when our living historians demonstrate how the Spanish settlers had to fight off Searle and his pirates.

Participation Rules

Online Registration takes place in the month prior to the event. You can also register onsite when you arrive. Searle’s Buccaneers annual membership dues of $20 dollars per person 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. Additionally, the Oldest House Museum requires a liability waiver be signed if you are camping on site. We appreciate your understanding in this matter. You will get this form when you arrive.

Encampment Setup

For those of you that can this year there is additional information for you. The setup and arrival time for the event will be after 5pm Thursday at the Oldest House Musuem. You can unload in the Oldest House Museum parking lot. To enter encampment parking use the driveway at 76 Marine St.  Drive  to parking lot directly behind the Oldest House Museum . Remember that you are on your own for food on Thursday.

If you arrive on Friday during the day or Saturday morning, please unload as quickly as possible then move your car to the parking area. Exceptions will be made for those with handicap access tags issued by a state DMV.

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 between 9 and noon.

Camp Regulations

As a condition of our grant, the encampment will be free to the public.

General Appearance, Guidelines and Suggestions

Behavior in Camp:
• The inappropriate public display of alcoholic consumption is not allowed.
• Please refrain from drinking alcoholic beverages during Oldest House Museum operating hours.
• Do not carry around with any alcoholic beverages in the encampment during the Oldest House Museum 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.”

There was little difference in the general appearance of St. Augustine’s Spaniards and the buccaneers 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. We know that Spanish artillery crews were issued blue uniforms faced with red in the early 1660s, before a similar uniform dress was applied to the infantry, though it is currently unknown whether these were in use in St. Augustine.

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. Buccaneers would look much like Spaniards, only more sea-faring garb – caps/head scarves, petticoat breeches, jerkins, earrings, etc. Their garb would be more eclectic and probably more worn – patched, stained with tar/rum/grease/wine/sweat/blood, ragged, etc. They wore what they could plunder, mostly, and wore it until it rotted away, or they could steal replacements. The most distinctive difference in the buccaneers’ appearance is that they would be MUCH better armed than the Spaniards. As professional raiders they carried

Registration Form

2023 searle’s Registration form PDF Download

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. If you think you know of a good advertising venue for our event, please let us know! (

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