5. Naples and Fort Myers: Luxury Hospitality, Golf Operations, and Consulting

Naples and Fort Myers represent the crown jewels of Southwest Florida’s Gulf Coast. Collier County boasts one of the highest concentrations of golf courses per capita in the world. As a result, private country clubs, golf resorts, and residential community associations continuously hire retirees for pro shop staffing, tournament management, starter and ranger roles, and dining room coordination.

The exceptional concentration of wealth in Naples creates unique consulting and professional opportunities. Retired corporate executives, attorneys, and financial planners frequently establish independent advisory services or seasonal concierge businesses catering to high-net-worth part-time residents (“snowbirds”). The region’s slower summer pace also allows you to work intensely for six months and take the remainder of the year off.