UPDATE: Check out our new 2023 Best Cities to Live in the U.S. list.

#2. Sarasota

Before it became one of the most popular places to retire, Sarasota, Fla., served as the winter quarters of the Greatest Show on Earth, the Ringling Brothers Circus. Today retirees enjoy a lion’s share of activities and things to do along with plenty of sunshine and comfortable temperatures. What makes Sarasota one of the greatest cities to retire in are the low costs of living, especially when it comes to health care, the high volume of golf courses and parks, and the large segment of people age 60 and older.


Find out where Sarasota ranks on our 2016 list of the 100 Best Places to Live


Retirement communities and assisted living centers can be found throughout Sarasota, as well as a variety of homes which range from beachfront mansions on the city’s keys to quaint bungalows near downtown. The Ringlings contributed greatly to the development and culture of Sarasota, and the city contains several memorials to the famous circus family, including John and Mable Ringling Museum of Art, the Ringling College of Art and Design and The Ringling International Arts Festival. A relatively flat terrain and tropical environment provide countless opportunities for retirees to engage in outdoor activities, and while there are numerous golf courses, there are plenty of other things to do in Sarasota. Fishing is a popular activity as well as kayaking, hiking and just enjoying the beach. In addition, the Baltimore Orioles hold spring training in Sarasota. Cultural opportunities include the Sarasota Ballet, Sarasota Opera and the Asolo Repertory Theatre.


Sarasota: One of the Top 10 Spring Break Cities for Families


Events like the Sarasota Film Festival draw celebrities and art lovers to the city. One of Sarasota’s top attractions is St. Armands Circle, which is located at the end of a bridge from the downtown harbor. The circle is surrounded by restaurants, shops and high-end homes.

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