Southwest Florida's snowbird crowd tends to assume Bologna is reachable only via some grinding multi-stop slog, but the reality is more elegant than that: there is no nonstop, of course, but a well-routed itinerary in business class from Fort Myers to Bologna can be done with a single, well-chosen connection and total travel time hovering around ten to twelve hours in the air. Delta typically routes travelers through Atlanta or JFK before handing off across the Atlantic, often in partnership with Air France-KLM metal, while Lufthansa's preferred path runs through Frankfurt or Munich, and Alitalia's successor ITA Airways (still ticketed under the AZ code) connects efficiently through Rome Fiumicino, which happens to be a genuinely pleasant gateway into Emilia-Romagna. I've flown all three configurations, and my strong recommendation is the Munich or Frankfurt connection on Lufthansa: their long-haul business class seats, especially where Allegris has been rolled out on select aircraft, offer far more privacy than the older staggered layout, and the shorter regional hop down to Bologna afterward is refreshingly low-stress.
The insider move that most travelers miss is booking the RSW–Atlanta or RSW–JFK domestic leg on Delta as a mileage upgrade candidate rather than paying full freight for the whole itinerary in business — domestic upgrades clear more easily than people expect out of Fort Myers, freeing budget for the transatlantic cabin where comfort actually matters. Arrive at RSW at least ninety minutes early even for connections; the airport's TSA lines swell dramatically during peak snowbird season from January through March, which conveniently is also when fares to Italy run highest, so it's worth avoiding that window entirely if flexibility allows.
The sweet spot for this route is April, May, September, and October, when Bologna's shoulder-season weather is glorious for exploring the Emilia-Romagna countryside and transatlantic business fares soften noticeably as leisure demand from the U.S. dips before summer or after it. Given how much these fares fluctuate week to week depending on which carrier is discounting inventory, setting up automated fare alerts for this specific Fort Myers–Bologna corridor is the smartest way to catch a premium seat before the window closes.
