The Bijou Cafe. Photo by Gus Pederson
The Bijou Cafe. Photo by Gus Pederson
Federal building. Photo by Gus Pederson
Federal building. Photo by Gus Pederson

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: Designed by Chicago architect Thomas Reed Martin, the Municipal Auditorium is one of the few surviving examples of the Art Deco/Moderne movement in Sarasota, featuring an arched roof and Art Deco-style glass blocks to optimize natural light. Construction began on the WPA-funded project in the summer of 1937, and the auditorium was officially opened in February 1938. The original structure included shuffleboard and tennis courts at the north side, which is now the auditorium parking lot. 
  2. Art Center Sarasota — 707 N Tamiami Trail:
    Art Center Sarasota
    Art Center Sarasota
    The Sarasota Art Association began in 1926, and went 20 years without an official home before the construction of the Art Center in 1948. The Art Center was designed by Frank Martin, son of Municipal Auditorium architect Thomas Reed Martin, in the Sarasota School of Architecture style, also known as Sarasota Modern. The original galleries, also designed by Frank Martin, were built around a patio of tropical plants and a sunken pool. Though the outdoor elements have since changed, today, an outdoor sculpture garden in front of the Art Center recalls the breezy nature of the Art Center’s original design.
  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. The Sarasota Garden Club building was designed in the Sarasota Modern style by architect John Cromwell, and contained a Japanese shoji enclosed garden. Three sides of the building were constructed of glass and shaded by wide roof overhangs. In 1962, architect Bert Brosmith designed a Japanese garden house to store the club’s gardening tools.
  4. J.B. Turner House — 1225 Fruitville Rd: The J.B. Turner House is one of the few remaining buildings in downtown Sarasota that were built prior to 1924. It is also one of the only rusticated stone block buildings—once a popular building method—that remains standing, and one of the rare examples of Colonial Revival style architecture in Sarasota. J.B. Turner, who moved into the house in 1913, is remembered as one of Sarasota’s most prominent merchants and one of its 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. Florida Studio Theatre — 1241 N Palm Ave:
    FST Performs "Hairspray"
    FST Performs "Hairspray"
    The Florida Studio Theatre (FST) is the cornerstone of contemporary American theatre in Sarasota. Originally built as a home for the Sarasota Woman’s Club in 1915, the Keating Theatre at the corner of Cocoanut and Palm is FST’s most historic building. FST’s Hegner Wing at the corner of Cocoanut Ave and 1st St includes the Goldstein Cabaret and historic Gompertz Theatre, where during renovations, workers found receipts and playbills dating back to the 1920s. The Gompertz space has been home to almost every performing arts group in Sarasota throughout its history.
  6. The Warren Building — 1269 1st St: Constructed in 1926, this Mediterranean Revival-style building was originally the office of prominent Florida Land Boom era realtor, Clark Warren, in the area then known as ‘Realtor’s Row’. Warren’s family home was directly behind the office. Warren’s dominant ad, “He knows where the money grows” reflected the intrepid attitudes of land developers and realtors in 1920s Florida. Though the real estate bubble burst in 1929, the Clark building remained. In the early 90s it was saved from demolition and renovated for use as a gallery. A hair salon called Salon First currently resides in the Warren Building.
  7. Bijou Cafe — 1287 1st St:
    Bijou Cafe
    Bijou Cafe
    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 and A’s is known as 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.
  8. Roast — 1296 1st St: This recognizable vine-covered building in downtown Sarasota’s Theatre Arts District has had several identities over the years. Today, the building is home to upscale American eatery, Roast. Constructed in 1925 by local businessman I.R. Burns in the area known as ‘Realtor’s Row’ during the Florida Land Boom, the building has primarily housed restaurants since the 1980s, including most recently the First Street Chop House and DJ’s. It’s also housed an antiques shop, The Conversation Piece, and several offices and city departments throughout its 90-year history in downtown Sarasota.
  9. Frances-Carlton Apartments — 1221-27 N Pineapple Ave: The Frances-Carlton Apartments were built in 1924 by Tampa architects, Francis James and Alex Browning. Browning came to Sarasota from Scotland as a young man in 1885 as one of the original settlers of what was then called the ‘Ormiston Colony’. Browning designed the home of Ormiston Colony leader, John Hamilton Gillespie, who became Sarasota’s first town mayor in 1902. The Frances-Carlton Apartments were named for the owner’s wife and son, Frances and Carlton. The Mediterranean Revival-style dwellings were originally advertised as furnished apartments. In 1952 the Frances-Carlton became Florida’s first cooperative apartment building. At the time, a 700 square-foot apartment could be purchased for $8000. The Frances-Carlton is currently managed as a condominium.
  10. Sarasota Opera House — 57 N Pineapple Ave:
    Sarasota Opera House
    Though J.H. Gillespie is recognized as the first mayor of the town of Sarasota, when the town grew, Arthur Britton (A.B.) Edwards became the first mayor of the City of Sarasota in 1914. Former mayor Edwards built the multi-use A.B. Edwards Theatre in 1926, designed in the popular Mediterranean Revival style of the era. At the time, the theatre hosted not only opera, but vaudeville and silent movies. In the 1930s, the Edwards Theatre became the Florida Theatre, and was used primarily as a movie theatre—but did in 1956 host Elvis Presley. Over the decades, the theatre underwent many changes and eventually fell into disrepair until renovation projects in the 1980s, 90s and early 2000s returned it to a state-of-the-art opera venue that retains a 1920s period elegance.
  11. Orange Blossom Hotel Building / American National Bank — 1330 Main St: This significant building was constructed in 1926 in the Neo-Classical style, a departure from the popular Land Boom-era Mediterranean Revival style, and is one of the first skyscrapers built in Sarasota. It is the work of architect Francis P. Smith, who designed some of the earliest skyscrapers in Atlanta. 1330 Main’s first incarnation was the American National Bank, which failed just two years after its construction, when the Land Boom bubble burst in 1928. 1330 Main was revived as the Orange Blossom Hotel in 1934 and remained a popular hotel until 1965, when it became a retirement residence. Today, the luxury Orange Blossom Tower Condominiums provide some of the most sought-after views of downtown and Sarasota Bay.
  12. Five Points Plaza — Pineapple, Main and Central Intersection: The bustling roundabout intersection known as ‘Five Points’ is, historically, the anchor of downtown Sarasota. The town’s first developer, J.H. Gillespie built Sarasota’s first boarding house at the Five Points location in 1886, shortly after his arrival to what was then called the fledgling ‘Ormiston Colony’. The boarding house was demolished in 1924, and in its place rose the First Bank and Trust Building, one of the first three skyscrapers built in Sarasota. Following the stock market crash of 1929, the First Bank and Trust dissolved and the more solvent Palmer Bank moved into the Five Points skyscraper. The building was eventually demolished in the 1990s and replaced by the current multi-story, multi-use condominium, retail, and restaurant space called Five Points Plaza.
  13. Kress Building — 1422 Main St.: Following the collapse of the Florida Land Boom and the beginning of the Great Depression across the nation, Sarasota entered a new period of development represented by the construction of the Kress Building 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 the Art Deco style in Sarasota. Though 1422 Main St. is no longer a five-and-dime, its facade maintains the iconic Kress logo seen on Main Streets across America.
  14. Worth’s Block (The Gator Club) — 1490 Main St:
    building in sarasota
    The Gator Club
    Constructed in 1912 at the corner of the dirt roads, Lemon and Main, Worth’s Block (today the Gator Club) is the oldest brick building on Main Street—and it has one of the most storied pasts. The ground floor of Worth’s Block originally contained a grocery store with dwellings on the second level, and a gas pump out front for cars and stoves. It was one of the only buildings to remain in operation after a fire in 1915 destroyed several businesses on Main Street. Worth’s Block became a cigar store in the late 1920s, and a second storefront was installed featuring a soda fountain that was popular with local teenagers. The cigar shop kept track of baseball scores on a ticker tape scoreboard, and Sarasotans gathered outside to keep tabs on sports standings—prior to the days of radios in every home. During the Prohibition Era, Worth’s Block’s second story was rumored to be a speakeasy, complete with gambling and other illicit activities. When Prohibition ended in the mid-1930s, the cigar shop was renamed the Gator Cigar Store, and the soda shoppe eventually became the Gator Bar. The building underwent extensive exterior and interior renovations in the late 1980s to return it to its original appearance, and was renamed The Gator Club—reflecting over 70 consecutive years of cocktail service in Main Street’s most spirited locale.
  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:
    Federal Building in Downtown Sarasota
    Federal Building in Downtown Sarasota
    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: post-Boom growth that was heralded by the arrival of the S.E. Kress Company in 1931. The Federal Building was originally constructed as a U.S. Post Office site, using the then-innovative material, aluminum, and 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 Murray Homes contractors building on the corner of Osprey and Main exemplifies the Sarasota Modern style of architecture that came into fashion in the Post-War era, from the late 1940s through early 1960s. The building was designed by celebrated American Modernist architect, Victor Lundy, in 1957 for Joe Barth Insurance. In the Sarasota Modern style, Lundy utilized natural elements of light and air: the building’s glass facade maximizes sunlight and street exposure for the business, and is joined by design elements such as breezy, ventilated spaces with shady overhangs and tropical landscaping. Most notably, buildings in the iconic Sarasota Modern style blur the line between indoors and outdoors.
  18. The Crisp Building — 1970 Main St: The Crisp Building is located in the east Main Street Courthouse Subdivision platted by circus magnate and Sarasota developer, Charles Ringling. It  was built in 1925 by the T.H. Crisp Company and provided 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.