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Florida

Signature City St. Augustine

Program No. 6642RJ
Explore culturally vibrant St. Augustine with historians and experts to learn the story of the nation’s oldest city through its architecture, art, monuments, Gilded Age works, and more.

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At a Glance

Bright and bold living history awaits you in beautiful St. Augustine, Florida — the oldest city in America. What began as a Spanish fortress has transformed over the centuries into a charming seaside town brimming with Spanish, British, and Venetian Renaissance architecture. Local experts spin gripping tales and present a dramatic overview of the city's remarkable history. Walk the sacred grounds of the Timucuan Indians with an archaeologist, understand the importance of the Civil Rights movement at the Lincolnville Museum, and immerse yourself in the city's unique Old World charm. Viva San Augustin!
Activity Level
On Your Feet
Walking up to 2 miles each day over varied terrain including stairs, narrow sidewalks and cobblestone streets; standing while on field trips.

What You'll Learn

  • Discover a unique tapestry of history through the shared passions of park rangers, scholars, authors, storytellers, and historians.
  • Learn about the Timucuan Indians who had a thriving civilization centuries before the Spanish and enjoy expert-led explorations of Spanish and British architecture.
  • See the Victorian era come alive at the Lightner Museum and understand the legacy of Henry Flagler and his grand hotels, admiring Gilded Age works of Tiffany glass in historic buildings.
Featured Expert
All trip experts
Profile Image
Roger Smith
Dr. Roger Smith, an expert in Early American history, has received numerous awards for his work on the American Revolution in the South. An adjunct professor of American history, he also represents Colonial Research Associates and speaks nationally on the Revolutionary War. He consulted for the AMC series “Turn” and was in the PBS documentary “Secrets of the Dead: The Secrets of Spanish Florida.” He has worked with Florida Humanities Council, University of West Florida, University of Florida, and the City of St. Augustine.

Please note: This expert may not be available for every date of this program.

Profile Image of Kenneth Barrett
Kenneth Barrett View biography
A native Floridian, Ken Barrett graduated from St. Joseph Academy and received degrees from Santa Fe Community College and the University of Florida. While associated with the National Park Service, Ken photographed parks in this region and organized their archives. A freelance photographer, Ken's work has appeared in a variety of publications, including, "The Houses of St. Augustine" and "Florida's Colonial Architectural Heritage." Ken is also a frequent exhibitor at Florida art shows.
Profile Image of Margaret Kaler
Margaret Kaler View biography
Margaret Kaler, from St. Augustine, studied theater at Florida State University and worked with the Asolo Theater in Sarasota. She specializes in re-enacting historical St. Augustine figures from Maria Malendez, a Timucuan woman, to Marjorie Kinnan Rawlings, author of “The Yearling.” She also acts and directs with local theater companies. A storyteller, Margaret serves on the board of the Florida Storytelling Association which produces the annual Florida Storytelling Festival. Audiences love her tales about growing up in St. Augustine, ghost stories, and history.
Profile Image of Marsha Chance
Marsha Chance View biography
Marsha Chance, a St. Augustine native, is an archaeologist, museum educator, and preservation consultant with 47 years of experience. With a master’s degree in Anthropology, she has served as an exhibit text author, graphics researcher, history camp director, and is presently the Curatorial Chair at the historic Pena-Peck House in St. Augustine. Marsha has also served on the Florida Historical Commission, the St. Augustine Lighthouse and Museum Board of Trustees, and the St. Johns County Historic Resource Review Board.
Profile Image of Ann Masters
Ann Masters View biography
Dr. Ann Browning Masters is a poet and 12th-generation Floridian. Her book “Floridanos, Menorcans, Cattle-Whip Crackers: Poetry of St. Augustine” features stories about mullet-netting, pilau-eating, and rum-running times in northeast Florida. Her writing has been recognized and recorded for the Florida State Historical Archives. In 2015, Masters was knighted by the St. Augustine Easter Festival for her dedication in promoting St. Augustine’s Spanish heritage. She enjoys sharing the beauty and drama found in St. Augustine from the Civil War through the Civil Rights Movement.
Profile Image of Charles Tingley
Charles Tingley View biography
Charles Tingley, a native Floridian, relocated to St. Augustine in 1978. He founded the Friends of St. Augustine Architecture, Inc., served on the city’s Historic Architectural Review Board, and is the Senior Research Librarian at the St. Augustine Historical Society. An award-winning writer, Charles has contributed to documentaries for the BBC, French National Television, PBS, NPR, and more, and had architectural photographs published in a work on the city’s historical architecture. In 2019, the St. Augustine City Commission gave him the de Aviles Award.
Profile Image of Roger Smith
Roger Smith View biography
Dr. Roger Smith, an expert in Early American history, has received numerous awards for his work on the American Revolution in the South. An adjunct professor of American history, he also represents Colonial Research Associates and speaks nationally on the Revolutionary War. He consulted for the AMC series “Turn” and was in the PBS documentary “Secrets of the Dead: The Secrets of Spanish Florida.” He has worked with Florida Humanities Council, University of West Florida, University of Florida, and the City of St. Augustine.
Profile Image of Charles Meide
Charles Meide View biography
Chuck Meide is a maritime archaeologist and director of the lighthouse archaeological maritime program of the St. Augustine Lighthouse & Museum in Florida. In addition to overseeing daily operations of the maritime archaeology program for the museum, Meide conducts field work (diving and searching wrecks), analysis, data work in the laboratory, and stabilization of the artifacts excavated. He discusses shipwreck archaeology in the United States' oldest port, showcasing a British Revolutionary War vessel he discovered.
Visit the Road Scholar Bookshop
You can find many of the books we recommend at the Road Scholar store on bookshop.org, a website that supports local bookstores.
Year
2025
  • 2024
  • 2025
Date
Apr 06 - Apr 11
  • Jan 05 - Jan 10
  • Feb 02 - Feb 07
  • Feb 23 - Feb 28
  • Mar 02 - Mar 07
  • Apr 06 - Apr 11
Please Note: The program differs on certain dates.
Please Note: The program differs on certain dates.
Select trip year and date
2025
  • 2024
  • 2025
Apr 06 - Apr 11
  • Jan 05 - Jan 10
  • Feb 02 - Feb 07
  • Feb 23 - Feb 28
  • Mar 02 - Mar 07
  • Apr 06 - Apr 11
While we make every effort to ensure the accuracy of our published materials, programs are typically advertised more than a year prior to their start date. As a result, some program activities, schedules, accommodations, personnel, and other logistics occasionally change due to local conditions or circumstances. Should a major change occur, we will make every effort to alert you. For less significant changes, we will update you during orientation. Thank you for your understanding.
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6 days
5 nights
12 meals
5 B 3 L 4 D
DAY
1
Check-in, Registration, Welcome Dinner, Orientation
St. Augustine, Florida
D
Casa Monica Resort & Spa

Activity note: Program registration from 3:00 p.m.-5:00 p.m. in the meeting room. Hotel check-in is 4:00 p.m. or later.

Afternoon: Program Registration: After checking in to your room, come to the Meeting Room located on the second floor to register and check in with the program staff and get your welcome packet containing an up-to-date schedule that reflects any last-minute changes. Orientation is at 5:00 p.m. sharp. If your arrival is delayed, please let your Group Leader know as soon as possible.

Dinner: Dinner will be served at the hotel in our private room.

Evening: Introductions and Orientation: Our Group Leader will kick off the program with introductions and a game or two so we get to know one another. Then we will review the program schedule in depth, discuss any changes, roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer any questions you may have. Free time has been reserved during the week for your personal independent exploration. Evenings at leisure offer opportunities to make the program more meaningful and memorable through engaging in available activities on your own, or simply relaxing and making new friends among fellow participants. The Group Leader will always be happy to offer suggestions of additional activities or best places to shop. Please note that program activities, schedules, and personnel may need to change due to local circumstances. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding. Continue getting to know your fellow Road Scholars, settle in, and get a good night’s rest for the full day ahead.

DAY
2
Before the Europeans, Historic District, Architecture
St. Augustine, Florida
B,L,D
Casa Monica Resort & Spa

Activity note: Boarding/disembarking trolley; walking up to 2 miles, sometimes on uneven terrain; stairs (no elevator) at the Oldest House.

Breakfast: Breakfast at the hotel.

Morning: Following breakfast, we'll walk to the St. Augustine Art Association for our first presentation and discussion of the early native Americans, the Timucuas, who called Northeast and North Central Florida and Southeast Georgia their home. It is believed that the Timucuas may have been the first Native Americans to see the Spanish explorers when they landed in Florida. At the time of the European contact it is believed this was home to a thriving community of 200,000+ Timucuas. From 1649-1656, the population began to diminish. War with the English and other Indians decreased their numbers and a series of epidemics further diminished their population, the major one being smallpox. In fewer than 250 years the Timucuas completely disappeared. Following this lecture by renowned anthropologist and archaeologist, we will take a guided archaeology walk through the historic district, an exclusive experience led by our expert.

Lunch: Our archeology walk ends at a local restaurant where we will have lunch.

Afternoon: After lunch, an open-sided trolley will take us for a non-stop narrated exploration of the Historic District. In this city occupied since the 1600s, we’ll see evidence of the Spanish, British and American occupations of St. Augustine and gain insight as to how people from each period may have lived. The guided trolley ride ends at the González–Alvarez House, also known as The Oldest House, where a docent will lead a guided tour. The González–Alvarez House, is now an historic museum. With a construction history dating to about 1723, it is believed to be the oldest surviving home in St. Augustine. It is also an important example of St. Augustine's Spanish colonial architectural style, with later modifications by English owners. It was designated a U.S. National Historic Landmark in 1970 and is now owned by the St. Augustine Historical Society. Following the tour, we will be joined by the founding president of the Friends of St. Augustine Architecture Society for a presentation on St. Augustine's “vernacular” architecture: design based on local needs, materials, and traditions that span the city’s history, adapted to meet changing times.

Dinner: Meet in the hotel lobby and we will walk to a nearby restaurant.

Evening: At your leisure.

DAY
3
The Europeans, Castillo de San Marcos, Minorcans
St. Augustine, Florida
B,L,D
Casa Monica Resort & Spa

Activity note: Walking up to 2 miles; some stairs, uneven terrain, especially at the Fort.

Breakfast: Breakfast at the hotel.

Morning: Begin the morning in our meeting room for an historical overview of St. Augustine's European era and the Castillo (Fort). Our presenter, a former National Park ranger, author, college professor and noted photographer, will also be our guide at the Fort. At the conclusion of the lecture, we’ll walk to the Historic District and Castillo de San Marcos. The Castillo is a monument not only of stone and mortar but of human determination and endurance. It symbolizes the clash of cultures which ultimately resulted in our uniquely unified nation. Still resonant with the struggle of an earlier time, these walls provide tangible evidence of America’s remarkable history.

Lunch: Take a short walk from the Fort to a local restaurant.

Afternoon: After lunch, we'll have a lecture on the British Period by a noted historian and scholar. Next, meet a fabulous author, retired college professor and historical interpreter. Through her engaging recollections and poetry "in the vernacular," she weaves together the history of Floridanos, Minorcans, and Crackers.

Dinner: We will meet in the hotel lobby and ride to a local restaurant.

Evening: At leisure.

DAY
4
Maritime Museum, Lincolnville Museum, Free Time
St. Augustine, Florida
B
Casa Monica Resort & Spa

Activity note: Boarding/disembarking an enclosed bus multiple times during field trips; walking up to 2 miles; some stairs, uneven terrain.

Breakfast: Breakfast will be at the hotel.

Morning: We'll ride to the historic St. Augustine Lighthouse and Maritime Museum. Here we will enjoy a lecture by a nationally- renowned maritime archeologist and explore the museum. Next, we’ll take a short ride to the Lincolnville Museum, which tells the story of the area's African American slaves and settlers, and the important role played during the Civil Rights era.Then we will head back to the hotel.

Lunch: This meal has been excluded from the program cost and is on your own to enjoy what you like. The Group Leader is happy to offer suggestions.

Afternoon: Free Afternoon: Take this opportunity for personal independent exploration to see and do what interests you most. The Group Leader is happy to offer suggestions and give directions.

Dinner: On your own.

Evening: At leisure.

DAY
5
The Age of Flagler: Meet Mrs. Flagler & See Flagler's Legacy
St. Augustine, Florida
B,L,D
Casa Monica Resort & Spa

Activity note: Walking up to 2 miles; some stairs (elevator may not be available at all sites), uneven terrain.

Breakfast: Breakfast at the hotel.

Morning: Henry M. Flagler's legacy as railroad tycoon, hotelier, and "Father of Tourism" is deeply appreciated and acknowledged in St. Augustine and the State of Florida. We will meet in the lobby and walk to the grounds of the Lightner Museum and be joined in the historic chapel by one of the first individuals to realize the potential of this titan of industry, the love of his life and first wife, Mary Harkness, in the person of our noted professional actor. Following that presentation, we will transition to the Lightner Museum, where our docent guides will share with you the museum's rich past and lead you through select galleries. The Lightner Museum is housed in the former Alcazar Hotel built in 1888 by Henry Flagler. Today it is home to one of the best collections of fine and decorative 19th century art in the country.

Lunch: We will walk a few blocks to lunch at a local restaurant.

Afternoon: After lunch we'll walk (approximately 3 blocks) to Memorial Presbyterian Church. Built in 1889 as a memorial to Flagler's daughter and infant granddaughter who died that year, this church is an elegant example of Venetian Renaissance architecture. Following our tour, we’ll move on to Flagler’s magnificent Ponce de Leon Hotel that set the standard for luxury in 1888, and became the centerpiece of Flagler College in 1968. We’ll hear from an expert student leader who will share information about the first of the luxury hotels Flagler built on the east coast of Florida. Learn how the building featured innovations such as a steam heating system and electricity as well as interior stained glass designed by Louis Tiffany. We then make our way back to the hotel.

Dinner: Enjoy our farewell dinner at a local restaurant.

Evening: At leisure.

DAY
6
Wrap-Up, Program Concludes
St. Augustine, Florida
B

Activity note: Hotel check-out is by 11:00 a.m.

Breakfast: Breakfast at the hotel.

Morning: In the hotel meeting room, our closing session will feature a recap of the week's highlights and sharing of our most memorable experiences. This concludes our program. We hope you enjoy Road Scholar learning adventures and look forward to having you on rewarding programs in the future.






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