Several alternative seismic retrofit and strengthening solutions have been studied in the past and adopted in practical applications ranging from conventional techniques, utilizing braces, jacketing or infills, to more recent approaches such as supplemental damping devices or advanced materials (e.g. Fibre Reinforced Polymers, FRP, or Shape Memory Alloys, SMA). A series of controversial issues are implicit in the complex decision-making process of seismic retrofit, where both rational and counter-intuitive solutions can satisfy some of the most critical aspects of multi-level performance-based seismic retrofit criteria. Interesting and fascinating suggestions and lessons can be obtained by reviewing the current trends in new design (i.e. innovative solutions for the future generation of buildings systems) as well as the architectural solutions used by the ancients. While walking this “bridge of knowledge” of our cultural heritage with the critical eyes of a curious and passionate observer, we can observe surprising commonality in engineering problems and their successful (and recently attempted) solutions. Understanding and implementing this heritage could lead to a uniquely stable platform for major breakthroughs in the development of “new solutions” in seismic design and retrofit.