Historical Walking Tour of Downtown Sarasota

This two-mile walking tour highlights the fascinating architecture and history downtown Sarasota, beginning on the west side of North Tamiami Trail at the Municipal Auditorium, and extending to the east end of Main Street at Washington Boulevard.

The Historical Walking Tour of Downtown Sarasota can be broken into two one-mile segments, with the Sarasota Opera House at 57 N Pineapple Avenue serving as the tour midpoint.

1. Municipal Auditorium — 801 N Tamiami Trail: The Sarasota Municipal Auditorium, designed by Chicago architect Thomas Reed Martin, is one of the few surviving examples of the Art Deco and Moderne movements in Sarasota. Its architecture features glass block work that optimizes natural light and a barrel-vaulted roof. Construction began on the WPA-funded project in the summer of 1937, and the auditorium was officially opened in February 1938. During World War II, the auditorium housed the Army Navy Club, and through the 1950s and 60s served as the Florida West Coast Symphony performance hall.
2. Art Center Sarasota — 707 N Tamiami Trail:

   

   The Sarasota Art Association began in 1926 and went 20 years without an official home before the construction of the Art Center in 1948. It was designed by Frank Martin, son of Municipal Auditorium architect Thomas Reed Martin, in the Sarasota School of Architecture (Sarasota Modern) style. The younger Martin designed the building's galleries around a patio of tropical plants and a sunken pool. Though some design features have since changed, an outdoor sculpture garden in front of Art Center Sarasota celebrates a balance of art and the natural world, as Martin intended.
3. Sarasota Garden Club — 1131 Blvd of the Arts: Established in 1927, the Sarasota Garden Club maintained the landscaping at the Municipal Auditorium and the Sarasota Art Center long before they opened their own building in 1960, accompanied by a Japanese garden house for tool storage, built in 1962. The garden club building was designed in the Sarasota Modern style by architect John Cromwell, and contained a Japanese shoji enclosed garden. Bert Brosmith designed the garden house. Next door to the Garden Club, catch a glimpse of the eye-catching 1956 "Blue Pagoda" building by famous architect Victor Lundy.
4. J.B. Turner House — 1225 Fruitville Rd: The J.B. Turner House is one of the few remaining buildings in downtown Sarasota built prior to 1924. It is also one of the only rusticated stone block buildings, and a rare local example of the Colonial Revival style. J.B. Turner, who moved into the house in 1913, was a prominent local merchant and one of Sarasota's first automobile owners. He is also remembered for building the first parking lot in Sarasota — a 100’ x 35’ covered lot behind his store on Main Street.
5. Frances Carlton Apartments — 1221-27 N Pineapple Ave:

   

   The Frances-Carlton Apartments were built in 1924 by Tampa architects, Francis James and Alex Browning, the latter of whom arrived in Sarasota in 1885 as a settler of the Scottish 'Ormiston Colony' and designed the home of colony leader, John Hamilton Gillespie—Sarasota’s first town mayor, elected in 1902. These Mediterranean Revival-style dwellings were originally advertised as furnished apartments, and in 1952 the Frances-Carlton became Florida’s first cooperative apartment building. At the time, a 700 square-foot apartment could be purchased for $8,000.
6. Florida Studio Theatre — 1241 N Palm Ave:

   

   Florida Studio Theatre (FST) is the cornerstone for contemporary American theatre in Sarasota. Built in 1915 to house the Sarasota Woman’s Club, the Keating Theatre at the corner of Cocoanut and Palm is the oldest building in the FST complex. The Hegner Wing at the corner of Cocoanut Ave and 1st St features FST's historic Gompertz Theatre, where during renovations in the 2010s, workers found receipts and playbills dating back to the 1920s. Over the course of a century, the Gompertz stage has hosted nearly every local performing arts group.
7. The Warren Building — 1269 1st St: Constructed in 1926, this Mediterranean Revival-style building served as the office of prominent Florida Land Boom era realtor, Clark Warren. It stood along what was then known as ‘Realtor’s Row.’ Warren’s advertising catchphrase, “He knows where the money grows” reflected the intrepid attitude of 1920s Florida realty tycoons. The real estate bubble burst in 1929, but the Clark building remains in use as commercial space.
8. Bijou Cafe — 1287 1st St:

   

   Believe it or not, this charming, upscale cafe was originally a filling station. Today, the structure that was built in the 1920s to fill the tanks of Ford Model T’s is one of the most longstanding, popular restaurants in downtown Sarasota. The Bijou Cafe opened in 1986 and is known for its award-winning wine list and continental cuisine.
9. I.R. Burns Building — 1296 1st St: This recognizable vine-covered landmark has lived a storied century. It was constructed by local businessman I.R. Burns in 1925 to anchor the area then known as 'Realtor's Row' during the height of the Land Boom -- but following the real estate bubble bust, the building has changed identities over the decades. The I.R. Burns Building has housed an antiques shop, commercial offices, City operations, and since the 1980s, has primarily housed high-end restaurants serving the Theatre District. 
10. Sarasota Opera House — 57 N Pineapple Ave:

    

    The Mediterranean Revival-style Edwards Theatre (later called the Florida Theatre) was built in 1926 to showcase top entertainment of the era. Live vaudeville acts and silent film showings evolved into big band performances and "talkies" through the 1930s and 40s, and in early 1956: a 21-year-old Elvis Presley performed four shows at the Florida Theatre just months before his skyrocket to hip-gyrating fame on "The Ed Sullivan Show." The Florida Theatre served as a movie theatre until the 1970s. Renovations starting in the 1980s returned the site to its former glory—its design celebrating 1920s elegance, combined with state-of-the-art acoustics, in the Sarasota Opera House.
11. Orange Blossom Hotel Building / American National Bank — 1330 Main St: Constructed in 1926, this building by renowned Atlanta architect Francis P. Smith was one of the first skyscrapers in Sarasota. Notably, it represents Neo-Classical design—a departure from local contemporaries' Mediterranean Revival style. The building first housed the American National Bank, which failed after just two years when the Florida real estate bubble burst in 1928. The site was revived in 1934 as the Orange Blossom Hotel, until 1965, when it became a retirement residence. Today, it houses the luxury Orange Blossom Tower Condominiums.
12. Five Points Plaza — Pineapple, Main and Central Intersection: The intersection at Five Points has anchored downtown Sarasota since before there was a downtown. Sarasota's first developer and town mayor J.H. Gillespie built a boarding house at Five Points in 1886, shortly after his arrival to what was then a modest pioneer settlement. The First Bank and Trust skyscraper replaced the boarding house in the 1920s, and later housed the Palmer Bank through the 1970s. The skyscraper was demolished in the 1990s, and the Plaza at Five Points (50 Central Ave) sits on its former site. Selby Five Points Park (1 Central Ave) remains the heart of downtown as a green space that connects the Sarasota Opera House, Selby Library, and other downtown entertainment, shopping and dining.
13. Kress Building — 1422 Main St.: When the Great Depression hit the nation shortly after the Florida real estate bubble popped, Sarasota entered a more austere period of development represented in the Kress Building, which was built in 1932. S.E. Kress & Co. was a national chain of “five-and-dime” style retail department stores, and the corporation’s arrival in Sarasota was hailed by the local press as a much-needed economic boost. The Kress Building is one of the few remaining examples of Art Deco architecture in Sarasota.
14. Worth’s Block (The Gator Club) — 1490 Main St:

    

    Constructed in 1912 when Main Street was a dirt road, Worth’s Block is among downtown Sarasota's oldest original structures. Indeed, it is one of the few survivors of a 1915 fire that devastated Main Street. Its ground floor was originally a grocery store, and there were second-level dwellings and a gas pump out front — which most early townsfolk used to fuel their kitchen stoves rather than cars. Worth's Block became a cigar store in the late 1920s, installed a soda fountain, and tracked baseball scores on a ticker tape scoreboard in the years before radios were a household item. During Prohibition, the building's second floor was a rumored speakeasy. In the 1930s, the cigar shop was renamed Gator Cigar Store, and the soda shoppe eventually became the Gator Bar. The building underwent extensive renovations in the 1980s and took its current name, The Gator Club. Today, it boasts over 70 consecutive years of cocktail service—probably a few more if the speakeasy rumors are true!
15. First National Trust — 1586 Main St: This rare surviving example of Neoclassical Revival architecture in Sarasota was originally the headquarters of the First National Trust Company of Sarasota, which specialized in insurance, bonds and mortgage loans — millions of dollars of which contributed to the development of Sarasota during the 1920s Land Boom. In the 1930s, the 1586 Main building became a hardware store, contributing in a different way — provision of raw building materials — to a later phase of local development. Today, the building once again specializes in banking as the Canandaigua National Trust.
16. The Federal Building — 111 S Orange Ave:

    

    The Federal Building is a significant example of the Neoclassical Revival style and WPA-funded architecture in Depression-era Sarasota. Constructed in 1932, the Federal Building, like the Municipal Auditorium, was a WPA project that represents a fourth phase in local development: the post-Boom growth heralded by the arrival of the S.E. Kress Company in 1931. The Federal Building was originally constructed as a U.S. Post Office using what was then a new and innovative material—aluminum—paired with classic marble. At the time of construction it was lauded by the press for its state-of-the-art modern plumbing, heating and ventilation.
17. Murray Homes — 25 S Osprey Ave: The eye-catching midcentury Murray Homes office space on the corner of Osprey and Main exemplifies the Sarasota Modern style, which emerged following World War II and was prevalent through the early 1960s. Notably, buildings in this iconic regional style blur the line between indoors and outdoors. The building was designed by the celebrated American Modernist architect Victor Lundy in 1957 for Joe Barth Insurance, and prioritizes natural light and airflow in its design. The building’s glass facade maximizes sunlight and street exposure for the business, and is joined by Sarasota Modern design elements: breezy, ventilated spaces with shady overhangs and tropical landscaping.
18. The Crisp Building — 1970 Main St: The Crisp Building is located in the east Main Street Courthouse Subdivision, which was platted by circus magnate and Sarasota developer, Charles Ringling. It was built in 1925 by the T.H. Crisp Company, providing a valuable space for retail as well as fraternal activity: the Crisp Building was the home for the Royal Order of the Moose, Sarasota Chapter, until 1938. It is one of the best surviving examples of the Boom-era Mediterranean Revival style, and is historically relevant as a catalyst for the growth of downtown Sarasota's east end.
19. Sarasota County Courthouse — 2000 Main St: After Sarasota separated from Manatee to become its own county in 1921, its judicial seat initially operated from the same building that housed City Hall before the Sarasota County Courthouse was designed by architect Dwight James Baum and built by Stevenson and Cameron, Inc. at the east end of Main Street. It was completed in 1927. The Courthouse's H-shaped structure and Spanish-Mediterranean Revival style courthouse design trends common in Florida in the 1920s. The judicial wing on the east side of the building contained the courtrooms and jail, while the west wing provided office space for Sarasota County commissioners and the tax collector, as well as teaching space for farm and kitchen demonstrations, public health, and other instruction.
20. Visitors Information Center — 1945 Fruitville Rd:

    

    The Visitors Information Center is your one-stop shop for info about what to do and where to go during your visit to Sarasota County. Its physical location provides walkable access to all of downtown Sarasota, in addition to the neighboring historic Gillespie Park neighborhood and historic Rosemary District. Scan the QR Code visible on entrance to the the Downtown Sarasota Visitor Center and Visitor Information Vehicle (VIV) for instant digital resources, or reach the Visitor Center by phone Monday-Friday at 941-706-1253, or by email at [email protected].