Archaeological museums play a vital role in regions with ancient roots, holding a millennial image as the cradle of civilization. In the South of Italy (former “Magna Graecia”) and particularly in Puglia—a melting pot of cultures where ancient Messapian, Byzantine, Roman, and Greek civilizations followed one another in ages, bequeathing a wealth of testimonies—institutions are disseminated across the region, and almost every small municipality has its own archaeological museum hosting a wealth of valuable objects and remains. The gradual structural changes in the role of museums over the last decades and the recent COVID-19 pandemic outbreak, with the sudden closing and subsequent re-opening of facilities, forced institutions to re-think and re-develop their communication practices everywhere. Museums across the world have since been conceiving original and effective strategies based on social media and ICTs. After framing the problem background, the article introduces an overview of good practice and virtuous examples in the museum field and a questionnaire-based focus survey on a sample of archaeological museums in Puglia in order to assess the status of local communication strategies’ implementation against the potential of modern technologies. The survey results allowed identifying a peculiar mix of “emergency” and evolutional approaches in the sample analyzed, main concerns and barriers to the adoption of digital strategies, but also specific strategic drivers for innovation in the very nature of local small institutions. The study’s outcomes offer a potential contribution to the alignment of institutions to current standards through informed policies that can be usefully shared in other similar contexts across Europe.