By Mike Miller Updated February 4, 2023
The oldest buildings in Florida are in St. Augustine reflecting the Spanish heritage dating back to 1565.
Many architectural masterpieces in the rest of the state were constructed during Florida’s Gilded Age of the late 1880s and early 1900s.
Some of the most impressive buildings were built during the real estate boom of the 1920s and are still functioning as hotels or other businesses.
Florida also has its share of historic mansions, many of which have been preserved and converted to museums.
Here are some of our favorite places to visit:
Ancient Spanish Monastery, North Miami Beach
Biltmore Hotel, Coral Gables
Bok Tower Gardens, Lake Wales
Breakers Hotel, Palm Beach
Ca'da'Zan (John Ringling Home), Sarasota
Cassadaga Spiritual Camp, Cassadaga
Coral Castle, Miami
DeFuniak Springs Historic District, DeFuniak Springs
Flagler Museum (Whitehall Mansion), Palm Beach
Ponce de Leon Hotel (Now Flagler College), St. Augustine
Florida Citrus Tower, Clermont
Florida State Capitol Buildings, Tallahassee
Frank Lloyd Wright Child of the Sun, Lakeland
Miami Marine Stadium, Miami
Ocean Drive Art Deco District, Miami Beach
Oldest House Museum Complex, St. Augustine
Pensacola Historic Village, Pensacola
Seaside Planned Community, Seaside
Tampa Bay Hotel (Now University of Tampa), Tampa
Vizcaya Museum and Gardens, Miami
Ybor City Historic District, Tampa
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DAY TRIP 1
Ancient Spanish Monastery
16711 West Dixie Highway,
North Miami Beach, Florida 33160
Don’t feel tricked, but although it truly is Florida’s oldest building, there is a catch.
The monastery was actually built in Spain in 1141. It was purchased by William Randolph Hearst, taken apart stone by stone and shipped to America.
It finally ended up here in North Miami Beach. The building is more than 400 years older than some of the national historic monuments in St. Augustine.
The buildings and grounds are beautiful and have become a popular place for weddings and other special ceremonies. Church services are held on Sundays and weekdays.
DAY TRIP 2
1200 Anastasia Ave, Coral Gables, FL 33134
The Biltmore is an operating luxury hotel and resort where you can spend some luxurious time in magnificent surroundings. The hotel was built in 1926 and when completed was the tallest building in Florida at 315 feet.
Its swimming pool is one of the largest in the world, and the hotel has been used as a setting for many movies and television programs.
The rich and famous stayed there, including the Duke and Duchess of Windsor, President Franklin D. Roosevelt, Bing Crosby, and even the infamous Al Capone.
You can play golf there, and even take a popular three-hour culinary class conducted by the Biltmore Culinary Academy.
DAY TRIP 3
Bok Tower Gardens
1151 Tower Blvd, Lake Wales, FL 33853
The quiet gardens and serenity of Bok Tower is a pleasant contrast to the busy activity of the theme parks in Orlando and elsewhere in Central Florida.
This attraction is only one hour from Orlando but it seems far away from the traffic.
Edward Bok was the editor of the Ladies Home Journal and transformed this sandy hill near Lake Wales into one of the most beautiful places in the country.
The tropical plantings give shade to visitors and home to more than 100 species of birds.
The singing tower with its carillon plays concerts every day at 1:00 pm and 3:00 pm, and shorter musical pieces at other times during the day.
Bok Tower Gardens has also become one of Florida’s most popular wedding venues.
DAY TRIP 4
One South County Rd, Palm Beach, FL 33480
The Breakers is a 538-room operating hotel and resort on the Atlantic Ocean that was opened in 1896 by Florida railroad tycoon Henry Flagler.
If you stay at this resort you will be surrounded by the opulent history of Palm Beach. Many large conferences and conventions are held here, and the hotel has 2,000 employees.
The architectural design of The Breakers is described as Italian Renaissance inspired by the Italian villas of the 1400s.
The hotel has 9 restaurants, 2 18-hole golf courses, 4 swimming pools, and a private beach on the Atlantic Ocean.
DAY TRIP 5
Ca’da’Zan, Ringling Home
5401 Bay Shore Blvd, Sarasota, FL 34243
John Ringling made his fortune in the circus business. He and his brothers operated the circus known as “The Greatest Show on Earth”.
Ca’d’Zan is a mansion constructed in the Venetian Gothic Style. The name in English means “House of John”. In addition to the mansion, the Ringling complex includes the Museum of Art and the Circus Museum.
A museum ticket gets you into both museums, but not into the mansion itself. You can buy a special ticket that includes admission to the museums and a tour of Ca’d’Zan led by a docent.
There are so many tour and admission options that it is highly recommended you go to the website before visiting so you can make the right decision about what you want to see and what time you want to see it.
DAY TRIP 6
Cassadaga Spiritualist Camp
1112 Stevens St, Cassadaga, FL 32744
This historic old town is on the National Register of Historic Places and has preserved its original roots as a spiritualist camp. Several psychics and mediums live in this town and ply their craft.
There are many Victorian era cottages and homes in the camp where the spiritualists live and work. There are 40 certified mediums in the village, and many self-proclaimed healers who pride themselves on teaching people to tap into their own ability to heal themselves.
A hotel on site is reportedly home to ghosts, and there is a gift shop with crystals, stones, jewelry, DVDs and CDs and a large collection of books on spiritualism and metaphysics.
DAY TRIP 7
28655 South Dixie Hwy, Miami, FL 33033
Temporarily closed (we hope not forever) as of 4/11/21.
Ed Leedskalnin was about to be married to his 16-year old sweetheart in Latvia. She backed out the day before the wedding. Ed was broken hearted and left for America, ending up in Florida in 1918.
He decided to create a monument to his sweetheart and started work on his castle. Ed was five feet tall and weighed 100 pounds. This fact will amaze you when you see the size of the giant rocks he used to build his monument.
He did it all by himself. He carved 1100 tons of coral rock and moved them into locations on his property. He had no large machinery, and he did most of his work after sunset using kerosene lanterns for light.
Each section of the wall at Coral Castle is 8 feet tall, 4 feet wide and 3 feet thick. Ed died without ever revealing the mystery of how he was able to manipulate these giant rocks.
He only said he understood the law of gravity and the use of leverage.
DAY TRIP 8
DeFuniak Springs Historic District
City of DeFuniak Springs
71 US 90 West, DeFuniak Springs, FL 32433
This small panhandle city has a large collection of Victorian homes and other buildings surrounding the circular Lake DeFuniak in the historic downtown area.
The town was the summer home from 1885 to 1928 of the Chautauqua Assembly.
There are about 200 historic buildings around the lake and 40 of them are listed on the U.S. National Register of Historic Places.
The town only has 8,000 people, so this possibly represents the most historic buildings per capita of any town or city in the State of Florida.
DAY TRIP 9
Flagler Museum (Whitehall)
One Whitehall Way, Palm Beach, FL 33480
Whitehall was the luxurious 73 room mansion of railroad tycoon Henry Flagler.
When was completed in 1902, the New York Herald proclaimed that it was "more wonderful than any palace in Europe, grander and more magnificent than any other private dwelling in the world."
Today, Whitehall is a National Historic Landmark and is open to the public as the Flagler Museum, featuring guided tours, changing exhibitions, and special programs.
Many of the original furnishings are still in the building, as well as a large art collection.
DAY TRIP 10
Flagler College (Ponce de Leon Hotel)
74 King Street, St. Augustine, FL 32084
Flagler College is in the former Hotel Ponce de Leon.
This building is a memory trip for me. I spent a New Year’s Eve as a guest in this hotel many years ago. The hotel was built by railroad tycoon Henry Flagler in 1888 and is a National Historic Landmark.
You can take a tour and explore the courtyard while learning of the hotel's Spanish Renaissance architecture and of the techniques used to construct it.
Your tour will include a visit to the grand lobby with its 68-foot domed ceiling supported by 8 ornate oak caryatids.
In the dining room you will see 79 Louis Comfort Tiffany Stained Glass windows streaming light onto the beautiful hand-painted murals on the walls and ceiling.
You will also see personal photos and mementos from Henry Flagler and his family.
DAY TRIP 11
Florida State Capitol
Florida’s Capitol Complex
400 South Monroe St.
Tallahassee, Florida 32399
Tallahassee became the capital of Florida territory back in 1824 and has held onto this distinction through Statehood and beyond.
The old capitol building has been preserved and restored and is immediately next door to the modern tower that serves as the headquarters for Florida’s state government.
You can take a self-guided tour. The highlight of a tour is the trip to the top of the 22-story office building for a breathtaking view of Tallahassee from the observation deck.
DAY TRIP 12
Frank Lloyd Wright Child of the Sun
Florida Southern College
111 Lake Hollingsworth Drive
Lakeland, FL 33801
Florida Southern College in Lakeland is home to several buildings designed by Frank Lloyd Wright from 1941 to 1958.
This collection is named Child of the Sun. All the structures are on the National Register of Historic Places and are working buildings used by students and faculty.
The Child of the Sun Visitor Center has photographs, furniture and working drawings related to Wright’s work on the campus.
The Center also has a gift shop, and seasonal tours are offered of the Wright designed buildings by appointment only.
You can also tour the campus on your own. Maps are available in the tourism center.
DAY TRIP 13
Ocean Drive Art Deco District
The Art Deco Welcome Center
1001 Ocean Drive, Miami Beach, Florida
The Miami Design Preservation League was established to protect and preserve the Art Deco buildings known as Streamline Moderne.
These buildings were built in Miami Beach during the Great Depression and up to the beginning of World War Two. They are complemented by a mix of other designs, some known as Tropical Deco.
This part of Miami Beach - known as South Beach - has an interesting mix of well preserved and functioning hotels, restaurants, and shops with Art Deco, Mediterranean Revival, and Miami Modern Styles.
Walking tours can be arranged, or you can explore the neighborhood on your own.
DAY TRIP 14
Oldest House Museum Complex
14 St. Francis St, St. Augustine, FL 32084
The Oldest House Museum Complex is located across from the historic National Guard building in downtown St. Augustine.
Admission to the Oldest House Museum Complex includes a guided tour of Florida's Oldest House, a museum, a changing exhibit gallery, an ornamental garden, and a museum store.
The Oldest House is open from 10:00 a.m. to 5:00 p.m. daily, and tours run every half hour.
DAY TRIP 15
Pensacola Historic Village
120 Church Street, Pensacola, FL 32502
Historic Pensacola is a neighborhood of 28 historic buildings and museums.
The village is managed by the University of West Florida Historic Trust and is in the historic district of downtown Pensacola. The entire historic district features charming homes, museums, art galleries, restaurants, and shops.
Pensacola’s history goes back more than 450 years.
Among the properties you will see are the T.T. Wentworth, Jr. Museum; Pensacola Children’s Museum; Museum of Commerce; Museum of Industry; Old Christ Church; Tivoli High House, Dorr House; Julee Cottage, Fountain Park; and Colonial Archaeological Trail.
Both guided and self-guided tours are available.
DAY TRIP 16
Scenic Highway 30A
Between Panama City Beach & Destin
Seaside is a planned community created in 1981 on what had been an 80-acre private family retreat near Seagrove Beach. The community is a pioneer of the concept now known as New Urbanism.
Seaside has spurred the development of several hundred similar communities in Florida and elsewhere. It was also the setting for the movie the “Truman Show”.
The town is designed for pedestrians. You can park your car and wander all over town on trails and sidewalks.
The houses and other buildings are modern versions typical of Old Florida architecture with wide overhanging roofs, porches, and wood frame construction.
DAY TRIP 17
University of Tampa
(Tampa Bay Hotel)
Henry B. Plant Museum
401 West Kennedy Blvd
Tampa, FL 33606
Plant Hall, the University of Tampa’s central building, once housed the Tampa Bay Hotel. This resort was built in 1891, and the Moorish minarets atop the distinctive structure have long been seen as an "iconic symbol" of Tampa.
It was built by railroad magnate Henry B. Plant as a luxury resort hotel with more than 500 rooms and hosted such famous guests as Teddy Roosevelt and Stephen Crane.
The Henry B. Plant Museum is in the hotel and contains the actual furnishings enjoyed by the first guests to visit here.
The Museum accurately reflects the opulence of turn-of-the-century America and the vision of Henry B. Plant.
DAY TRIP 18
Vizcaya Museum & Gardens
3251 S Miami Avenue, Miami, FL 33129
The Vizcaya Museum and Gardens is the former estate of James Deering of the Deering-McCormick International Harvester fortune. It is on Biscayne Bay in the Coconut Grove neighborhood of Miami.
The estate was built in the early twentieth century and the landscape and architecture was influenced by Veneto and Tuscan Italian Renaissance designs.
Deering used Vizcaya as his winter residence from 1916 until his death in 1925.
Recent hurricanes have damaged some of the open-air exhibits here, but it is in the process of restoration and is well worth a visit.
DAY TRIP 19
Ybor City Historic District
Ybor City Visitor Information Center
1600 East 8th Avenue, Tampa, FL 33605
Tel: 813-241-8838 http://ybor.org/
You will enjoy walking the narrow brick streets of Ybor City and feeling its old-world charm.
Known as Tampa’s Latin Quarter for over a century, Ybor City is an exotic blend of aromas, flavors, sights and sounds.
From the scent of roasting Cuban coffee early in the morning to the rhythms of Latin music late into the night, Ybor is a feast for the senses.
Ybor City is a National Historic Landmark District founded in 1886 by Vicente Martinez-Ybor when he moved his cigar factory from Key West to Tampa.
Historic buildings have been preserved or converted to stylish offices, homes, and boutique hotels without sacrificing their historic character.
DAY TRIPS 20-39
Florida Carpenter Gothic Churches
Located in Various Florida Towns
We discuss 39 Carpenter Gothic Churches on our website and also 4 other churches of special interest.
Carpenter Gothic is a style of architecture that involves architectural details on wooden structures that try to replicate features that were originally carved in stone.
Most Carpenter Gothic churches in Florida were built between 1870 and 1900. Some sources indicate there may have been as many as 80 of these churches across the state at one time.
Almost all of the remaining churches are still active and welcome visitors for Sunday service, and many have open doors during the week for the convenience of visitors.
See photos of all 39 Florida Carpenter Gothic Churches.
If you enjoyed seeing these historic buildings and architectural sites, you will also enjoy Florida Historic Homes.
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By Mike Miller, Copyright 2009-2023
Florida Back Roads Travel is not affiliated with or endorsed by Backroads, a California-based tour operator which arranges and conducts travel programs throughout the world.