Orlando, Miami and Tampa retained the top three positions in WalletHub’s 2026 Best and Worst Places to Retire report, keeping Florida at the forefront of the city rankings. Orlando placed first for a second consecutive year, supported by Florida’s lack of state income, estate and inheritance taxes, access to health care and extensive recreational options. WalletHub assessed more than 180 U.S. cities across 45 measures covering affordability, taxes, health care, recreation and other retiree concerns. Orlando ranked second nationally for recreation, 21st for gerontologists, eighth-highest for home-healthcare facilities per capita, fourth for geriatric hospitals and 20th-cheapest for adult day-healthcare. Housing costs, property taxes and hurricane risks remained drawbacks. Stockton ranked last, while six of the 10 lowest-ranked cities were in California. With about 18% of the U.S. population now 65 or older and retirement potentially lasting decades, experts recommend weighing expenses, medical access, activities, work opportunities and lifestyle before moving. WalletHub analyst Chip Lupo suggested renting in a prospective destination for a year, including across peak and off-season periods, before buying or relocating permanently.