Introduction of a triisopropylsilyl group into allyl and allenyl carbinols greatly enhances the efficiency of gold(I)‐catalyzed cyclodehydration, which can provide rapid access to a library of various compounds including 1H‐indenes (Table 2 and Scheme 5), benzofulvenes (Table 3), indan‐2‐ones (Scheme 2), fulvenes (Table 4), cyclopentadienes (Table 4), 5H‐dibenzo[a,c][7]annulenes (Scheme 6) and dibenzosuberones (Scheme 6). The developed method enables unprecedented product generality for several classes of cyclodehydration reactions, which is particularly notable for the preparation of 1H‐indenes. The first synthesis of non‐benzo‐fused fulvenes via cyclodehydration of allenyl vinyl carbinols could be accomplished. The protocol is remarkable for mild conditions, operational convenience, and easy access to starting materials.