Road Scholar : Home
When Florida Was A Wild Frontier: Pirates, Smugglers, and Slavers in Amelia Island's Chaos Period

Program Number: 20196RJ
Start and End Dates:
1/5/2014 - 1/10/2014;
Duration: 5 nights
Location: Amelia Island, Florida
Price starting at: $645.00 - Price may vary based on date, departure city
Program Type: History & Culture
Meals: 13; 5 Breakfasts, 4 Lunches, 4 Dinners    
Meal Options: Vegetarian; Kosher; Gluten Free; Low Salt    

Behind the pleasant Victorian facade for which it is known, Fernandina Beach conceals a shadowy past. Smugglers, slavers, pirates, prostitutes, and audacious entrepreneurs hoping to get rich off illicit activities were the denizens of Fernandina Beach during its wild frontier days. Plumb the depths of this golden isle’s dark history with a cast of characters more colorful than anything Hollywood could create.


• At Kingsley Plantation, hear about Anna Kingsley, an African slave who became one of the most influential people in the region.
• Discover pirates, smugglers, slavers and the various other ne’er-do-wells of the early New World.
• Learn about Luis Aury, Gregor MacGregor and the other adventurers who vied for control of Fernandina and Florida.

Activity Particulars

Walking up to two miles.

Date Specific Information


Enjoy the latest in hearing technology — listening devices — on this date.

Coordinated by the Amelia Island Museum of History.

Amelia Island

Amelia Island is a picturesque resort community rich in history. It was the playground of the affluent, and today, visitors – as well as seasonal and year-round residents – enjoy its sandy beaches, colorful seaside villages and popular dining spots.

Comfortable hotel in historic downtown Fernandina Beach.
Meals and Lodgings
   Hampton Inn & Suites
  Fernandina Beach Florida 5 nights
 Hampton Inn & Suites
Type: Hotel
  Description: The Hampton Inn & Suites is located within walking distance to a variety of 50 eclectic shops and over 25 restaurants. At the Hampton Inn & suites Amelia Island Hotel you will experience the true taste of island life at its best in Florida.
  Contact info: 19 South 2nd Street
Fernandina Beach, FL 32034 USA
phone: 904-491-4911
  Room amenities: A coffee maker, iron and ironing board, and complimentary in-room movie channel is available in all rooms.
  Facility amenities: Amenities include a state-of-the-art fitness center, and complimentary deluxe continental breakfast, high speed Internet access in every room, wireless Internet access in the lobby, meeting rooms and public areas, coffee and tea in the café 24 hours a day, and USA Today copies (Monday-Friday). Hampton also offers a 24 hour front desk, message and fax service.
  Smoking allowed: Yes
  Elevators available: Yes
  Additional nights prior: $190 Guests must make additional night accommodations directly with the hotel.
  Check in time: 3:00 PM
  Additional nights after: $190 Guests must make additional night accommodations directly with the hotel.
  Check out time: 11:00 AM

Travel Details
  Start of Program:
3-5pm Hotel check-in & Road Scholar registration in lobby You will be staying at Hampton Inn & Suites that night.
  End of Program:
11am. Check out of hotel before leaving for first lecture You will be staying at Hampton Inn & Suites the night before.
  Required documents:
The Road Scholar Health & Safety Form is required. N/A
  Parking availability:
Plenty of parking available at the hotel and around town.
To Start of Program
  Location:  Fernandina Beach Florida
  Nearest city or town:  Jacksonville Florida
  Nearest highway: I-95
  Nearest airport:  JAX International Airport
  From End of Program
  Location: Fernandina Beach Florida
    (Additional transportation information same as above)
Travel Details



From Airport




VIP Taxi
phone: 904-753-6480
Advanced Reservations Required


Per Person/One Way:


Prices are subject to change.


Travel Time:






~25 miles


Ask for Vic and mention that you are with the museum's Road Scholar group. Call 24 hours before arrival time to confirm.

Driving Directions
  From Airport After exiting airport, follow airport road to I-95 North. Drive ~ 6 miles to exit 373. Follow directions from north/south
  From North(Savannah or Brunswick, GA) or South (Jacksonville, FL) on I-95 From Interstate 95, take exit 373 (Yulee, Fernandina Beach - SR 200/A1A) and turn east toward Amelia Island - about a 15 minute drive to the Thomas Shave Bridge. After crossing the bridge, continue on 8th Street (A1A) to Ash Street (1 block north of 6th stoplight). Turn left on Ash and drive 6 blocks to South 2nd Street. Turn right and you will see the hotel on your left.
  From West (Tallahassee) I-10 to I-95 - and follow directions from north/south
The prices listed for commercial services and facilities that are not included in the program cost, such as airport shuttles or extra nights lodging, are subject to change without notice. Since Road Scholar cannot guarantee the accuracy of these prices, we strongly suggest contacting the companies directly for the most up-to-date information.

Daily Schedule

Day 1: Hotel Check in & program orientation.
(Sunday, January 5)
 Arrive To: Participants will check in to hotel and meet the program hostess, Brenda. The group will then walk to a nearby restaurant and have dinner as a group. After dinner, the group will walk to the museum for the orientation presentation.
Accommodations: Hampton Inn & Suites

Day 2: Amelia Island's Back-story: The 8 Flags. Field Trips to Kingsley Plantation and American Beach
(Monday, January 6)
 Breakfast: Breakfast at the hotel
 Morning: Presentation: The Natives of Northeast Florida, presented. Discover the original natives of Amelia Island, the Timucua. The Timucua had a thriving civilization in the area until they were decimated by European war, slavery, and disease. Delve into the lives of these interesting people and their sad fate.
 Morning: Presentation: 8 Flags Over Amelia Part I (French, Spanish, and British). Explore the bloody beginnings of Florida history as 3 major European superpowers vie for control of Northeast Florida.
 Lunch: Lunch at one of Fernandina's many fine restaurants
 Afternoon: Presentation: 8 Flags Over Amelia Part II (Patriot, Green Cross, and Mexican Rebel). During the early 18th century, Florida became a chaotic hotbed of shadowy activity. Locally known as the Chaos Period, this era of Florida history is riddled with colorful characters and dubious activities. This program will be a brief overview of the period that will be discussed in far more detail throughout the week.
 Afternoon: Trip to Kingsley Plantation National Park The plantation's owner, Zebadiah Kingsley, married his young African slave, Anna Kingsley. After Zebadiah's death, Anna inherited her freedom and Zebadiah's substantial estate. She would go on to expand the plantation's operations and become of the area's most powerful women.
 Afternoon: Excursion to American Beach. Located on the south end of Amelia Island, American Beach was one of the few African American resort areas in the United States. Purchased by Abraham Lincoln Lewis (Florida's first African American millionaire) in 1935, American Beach became a thriving beach-side resort community during the age of segregation. Music greats, such as Cab Calloway and Louis Armstrong, frequented the beach's many clubs and many of America's most influential African Americans owned homes on the beach. Today American Beach is but a shadow of its former glory. Still boasting a strong African American community, American Beach is squeezed by modern development.
 Dinner: Dinner at one of Fernandina's many fine restaurants.
 Evening: Getting to know the art of Amelia. Take a break from the dark side of Amelia to enjoy a warm reception by the Amelia Island Art Association. Have a glass of wine as you get to better know your fellow participants and the thriving local art community.
Accommodations: Hampton Inn & Suites
Meals Included: Breakfast, Lunch, Dinner

Day 3: Amelia's Chaos Period: The Illegal Slave Trade, Black Pirates, and Secret Invasions
(Tuesday, January 7)
 Breakfast: Breakfast at the hotel
 Morning: Presentation: Fort Mose: Florida's Bastion of Black Freedom. The Spanish governor of Florida, fearing invasion from the British colonies to the north, takes drastic action. To bolster his forces, he offers freedom and land to any slaves that can make it to Florida and pledge their allegiance to Spain. Escaped slaves from Georgia and the Carolina comes by the thousands, and true to his word, the governor establishes Fort Mose for his new black soldiers. But how long would this exodus go unnoticed by the British plantation owners?
 Morning: Pirates: Fact or Fiction presented by Joe Anderson in AIMH's Baker Hall
 Lunch: Lunch at one of Fernandina's many fine restaurants.
 Afternoon: Guided excursion through downtown Fernandina Beach. The birthplace of the modern shrimping industry, Florida's oldest saloon, and plenty of Victorian architecture await as you explore one of Florida's best-kept secrets.
 Afternoon: Trip to Old Town, the Original Fernandina. Only a shadow of its former glory, Old Town boasted a fort, Spanish plaza, slave warehouses, and more. Currently a sleepy residential area, many of Old Town's landmarks have disappeared since Fernandina was moved in the 1850's.
 Afternoon: Presentation: Gregor MacGregor: The Greatest Huckster in History. In 1817, Amelia Island was invaded by a motley crew of mercenaries led by Gregor MacGregor. MacGregor, fresh from helping Simon Bolivar establish a free Argentina, sought to "liberate" Florida and establish another democratic state. Discover on of history's most colorful character as his exploits bring him to Amelia Island.
 Afternoon: Presentation: The Patriot Invasion of Northeast Florida: Under the Surface. During the chaos brought about by the War of 1812, a secret plot was hatched to steal Florida from Spain. With secret presidential approval, a group of rag-tag militia from the southern U.S. invaded northeast Florida. This small band of ruffians almost succeeded in securing Florida for the United States, but failed in what is locally called the Other War of 1812.
 Dinner: Dinner at one of Fernandina's fine restaurants.
Accommodations: Hampton Inn & Suites
Meals Included: Breakfast, Lunch, Dinner

Day 4: Amelia's Chaos Period: Pirates and Smugglers Galore!
(Wednesday, January 8)
 Breakfast: Breakfast at the hotel.
 Morning: Presentation: Smuggling: A Beginner’s Guide. Smuggling put Fernandina on the map (at least early on), but why was it so lucrative and what kind of goods were being smuggled? This lecture will discuss the economics of local smuggling throughout various eras and why it was such a big deal.
 Morning: Presentation: Luis Aury: Pirate, Privateer, Revolutionary. Amelia Island's 5th flag was strangely that of the Mexican Rebels. Hoisted by French-born pirate, Luis Aury, this short-lived flag came on the heels of MacGregor's occupation of the island. Fresh from Galveston, Texas and Mexico, Aury fancied himself a revolutionary, though most of the world would call him a pirate. This presentation will delve into the story of one of Fernandina's colorful conquers, Luis Aury.
 Lunch: Lunch at one of Fernandina's fine restaurants.
 Afternoon: Amelia's Victorian Tea in AIMH's Baker Hall
 Afternoon: Field trip to Fort Clinch. Situated on the northern tip of Amelia Island, Fort Clinch was built to defend Amelia Island and the mouth of the St. Marys River. It was largely built with slave labor, but would later become an icon for freedom when Union forces occupied the island during the American Civil War. It played an important role in curbing Confederate smuggling and training the escaped Confederate slaves that flocked to the island to be free.
 Dinner: Dinner at one of Fernandina's many fine restaurants.
 Evening: Conversations with History. The Amelia Island Museum of History boasts a cast of "1st person presenters". These costumed reenactors portray some of the area's more colorful historical characters. Part theater, part history, our first person presenters help bring history alive in a fun and engaging way.
Accommodations: Hampton Inn & Suites
Meals Included: Breakfast, Lunch, Dinner

Day 5: Field Trip down the Amelia River with lecture on historical sights
(Thursday, January 9)
 Breakfast: Breakfast at the hotel.
 Morning: Trip down the Amelia and St. Marys Rivers. Much of Fernandina's history revolves around her harbor. Boarding a boat and venturing out onto these historic waters gives us a unique vantage point to explore the island's turbulent past. The trip will feature points of historical interest and bountiful natural beauty as we explore the natural boundary between Florida and Georgia.
 Lunch: Lunch at one of Fernandina's many fine restaurants.
 Afternoon: Field Trip- From Smuggler’s Den to Victorian Seaport: A Trip through Fernandina’s Victorian District. After the end of the Civil War, union soldiers would return north with tales of Fernandina's warm weather and beautiful scenery. Northern steamers would establish routes to Fernandina and the area would quickly evolve from a shadowy backwater harbor to a Victorian hot-spot. This new influx of tourism and the development of the area's natural resources would catapult Fernandina into a golden age. This trip through Fernandina will highlight the remnants of Fernandina's dark past, juxtaposed to Fernandina's celebrated Victorian mansions and churches.
 Afternoon: Presentation: Amelia Island in the Civil War: Secession, Occupation, and Black Recruiting Grounds. Shortly after becoming part of the United States, America was gripped by civil war. Florida sided with the newly formed Confederacy and seceded from the union. As part of its Anaconda Strategy, the Union forces blockaded or occupied many southern harbors to starve the confederates of much needed supplies and trade. In 1862, union forces landed on Amelia Island as confederate forces withdrew to areas deemed more important to the war. Occupied by the union, Fernandina became a symbol for freedom in the deep south and thousands of slaves would flee their plantations in hopes of reaching Amelia Island and their freedom. Many of these newly freed slaves would be formed into the 1st South Carolina Volunteers, the first African American fighting unit in U.S. history.
 Afternoon: Presentation: The Seminole Wars: Florida’s Turbulent Entrance Into the U.S. As the United States pushed westward, many displaced Native Americans were forced onto reservations or into lands not yet owned by the U.S. Remnants of the once great Creek, Choctaw, and Miccosukee tribes defied the U.S. and fled to Spanish Florida. Knowing that America would be reluctant to invade Spanish Florida, this newly created Seminole tribe use Florida to stage attacks into Georgia and Alabama. Known as the Seminole Wars, a number of conflicts were fought to counter the Seminoles' activities in Florida which would bring the U.S. and Spain to the brink of war. Involving familiar characters like future president Andrew Jackson and Chief Osceola, the Seminole Wars would eventually lead to Florida joining the U.S.
 Dinner: Dinner at one of Fernandina's many fine restaurants.
 Evening: Haunted History: Explore Fernandina's shadowy and unexplained happenings. Any old town has its share of ghost stories. A town with Fernandina's turbulent past has more than its share of restless souls. discover some of her dubious happenings and legends that surround them.
Accommodations: Hampton Inn & Suites
Meals Included: Breakfast, Lunch, Dinner

Day 6: Hotel Check-out & Program Wrap-up
(Friday, January 10)
 Depart From: Program wrap-up: Collect name tags, do evaluations, stamp passports and receive boxed lunches. Program concludes.
 Breakfast: Breakfast at hotel. Check out of hotel.
 Morning: 1st Person Presentation by John Broadbent. Enjoy a costumed reenactor portraying John Broadbent, one of Fernandina's more colorful and reclusive residents.
Meals Included: Breakfast
Important information about your itinerary: Every effort has been made to ensure the accuracy and completeness of the information featured on this website. Itineraries are based on our best information at this time. Circumstances beyond our control may require us to adjust itineraries or other details. We regret any inconvenience this may cause and appreciate your understanding. Information will be sent to you from your Program Provider approximately three weeks prior to the program start date. The prices listed for commercial services and facilities that are not included in the program cost, such as airport shuttles or extra nights lodging, are subject to change without notice. Since Road Scholar cannot guarantee the accuracy of these prices, we strongly suggest contacting the companies directly for the most up-to-date information.

You can't find a better value than Road Scholar.

As a not-for-profit organization, we are dedicated to providing all-inclusive educational programs at great value. From lectures to gratuities to field trips to accommodations - the tuition you pay up front is all that you pay.

Specifically, this program includes:

Plus these special experiences...

View the Daily Schedule to see more

And included with all Road Scholar programs:

© Road Scholar 2015 | Call toll-free: 1-800-454-5768