24 Small Town Escapes in America Perfect for a Relaxing Retirement

17. St. Augustine, Florida – History Meets Coastal Living

If you love Florida’s warm weather but want something less touristy and more historic, St. Augustine is an excellent choice. As the oldest city in the U.S., this town is packed with charming Spanish-style architecture, cobblestone streets, and beautiful beaches. It offers all the perks of Florida living—without the high prices of places like Naples or Sarasota. Retirees enjoy mild winters, a thriving arts scene, and plenty of festivals, outdoor markets, and historic sites to explore year-round.