Sarasota, Florida was recently ranked the number one place in America to retire by the TopRetirements.com website. Experience downtown sarasota Florida and It’s not hard to see why, with its pleasant weather and low cost of living. But what many might not realize is that Sarasota has a distinct cosmopolitan feel with a thriving arts and cultural community.

downtown sarasota florida

Visitors windows shop on Main Street in Downtown Sarasota Florida.

Sarasota’s downtown has a large number of high-rise office and residential buildings giving the area a distinct and impressive skyline. But unlike many other downtowns, Sarasota’s is not only very walkable but has a charming small town feel.

Development in Sarasota never really took off until the early twentieth century when Florida began to be seen as a playground for the rich and a way to avoid the harsh winters up north. Many wealthy people settled in Sarasota or built residences there. One such person was John Ringling, the circus magnate. Ringling was a patron of the arts and many of the works he owned can be found today in the John and Mable Ringling Museum of Art. Ringling’s influence helped make Sarasota the cultural capital it is and led the area around it to be known as the Cultural Coast. Much of this influence is still felt in the city today, especially with its numerous museums and performing arts venues.

The center of Downtown Sarasota is known as Five Points and it’s at the intersection of Main Street, Pineapple Avenue, and Central Avenue. Most shops, restaurants and other businesses can be found along Main Street, Palm Avenue, and First Street. There is a wide selection of restaurants and cafes. Many of the shops cater to the wealthy residents and snowbirds and sell high-end fashion, art, and home decor.

Palm Avenue, which intersects Main Street, is home to many art galleries and luxuriant antique stores. First Street, which runs parallel to Main Street just one block north, features a redeveloped block between Lemon and Central with new high rise condos and posh boutiques on the ground floor. Main Street itself actually continues east for a couple of miles, but the area with the most shops and restaurants is between Gulf Stream to the west and Orange Avenue to the east.

Originally, a lot of thought went into the planning of the town in the 1920s with roads running along Sarasota Bay before transitioning to a grid further east. Unfortunately, in the 1960s, a major highway, Tamiami Trail was rerouted along the Bay and became Bayfront Drive. This highway separates the waterfront from the more walkable downtown area and can be dangerous to cross. There have been some talk of redeveloping the area to make the highway less dangerous and more walkable, including adding roundabouts to help slow traffic.

downtown sarasota florida

High-rise condos overlook Main Street in Downtown Sarasota.

Also in the city of Sarasota is the St. Armands Circle area, which has its own listing on our site. The two areas each have a different feel. St. Armands Circle is closer to the beach and has more tourists. Meanwhile Downtown Sarasota’s atmosphere is reflected by the fact that it’s the area’s central business district. Also Downtown Sarasota tends to be quieter in the summer time when there are fewer vacationers and snowbirds.

There is a small rivalry between the two areas. One example is parking. Downtown Sarasota had parking meters for a short time while St. Armands Circle did not, which many business owners in downtown sarasota florida considered to be unfair since it gave St. Armands Circle an unfair advantage. Fortunately, the meters have since been removed. Either way, a full trip to Sarasota would not be complete without a visit to both areas.

Read more about downtown sarasota floridas condos at Downtown Sarasota Condo.