Gold(I)-catalyzed tandem cyclization reactions of 2-hydroxyalkyl-3-propargylindoles enable rapid access to indole-fused cyclic ethers via vinylogous reactivity of α,β-unsaturated gold-carbene intermediates. Selective intramolecular Michael attack of O-nucleophile, supported by DFT studies, affords six-, seven-, and eight-membered O-heterocycles under mild conditions. One-pot hydrogen transfer further delivers reduced pyranoindoles, highlighting the versatility and synthetic potential of this method.