In order to extend the “eating window”, the optimum ripening phase suitable for eating, the combination of treatment with propylene (an ethylene analog) and 1-methylcyclopropene (1-MCP; an ethylene inhibitor) was assessed in three kiwifruit cultivars: ‘Rainbow Red’ Actinidia chinensis, ‘Sanuki Gold’ A. chinensis, and ‘Hayward’ A. deliciosa. Propylene treatment initiated the ripening process by inducing fruit softening, increasing soluble solid content (SSC), and decreasing titratable acids (TA), with or without endogenous ethylene production, depending on the duration of exposure. Once endogenous ethylene was induced, it accelerated fruit ripening, resulting in an over-ripening phase and shortening of the “eating window”. ‘Rainbow Red’ and ‘Sanuki Gold’ fruit treated with propylene continuously or for 48 h initiated endogenous ethylene production that led to an “eating window” lasting only 2 days (range of 3–5 days after the start of treatment), whereas it lasted for 7 days (range 3–10 days) in ‘Hayward’ fruit. Limited propylene treatment of the three cultivars for 24 h induced ripening without the detection of ethylene production, suggesting that the optimum ripening phase suitable for eating can be attained without endogenous ethylene production, resulting in a longer “eating window”. ‘Rainbow Red’ and ‘Sanuki Gold’ fruit treated with propylene for 48 h followed by 1-MCP treatment had extended “eating window” and shelf-life, with the suppression of endogenous ethylene. These results illustrate the practicability of different durations of propylene treatment in facilitating kiwifruit ripening and the additional benefit of 1-MCP treatment to the extend shelf-life of new high-quality kiwifruit cultivars, ‘Rainbow Red’ and ‘Sanuki Gold’.