This paper investigates how Social Shopping and Customization interplay to affect Digital Millennials’ online shopping experience. We test whether the social richness of online shopping in pairs can overcome the leanness of the online shopping experience. Can the interactivity of Online Customization accomplish the same purpose? Is there a synergistic, interaction effect? Our 2x2 experimental design with 182 subjects examines this question with customizable versus packaged vacation travel. Analyses of Perceived Effectiveness, Perceived Ease of Use, Perceived Enjoyment and Intent to Purchase suggest that a user’s Intention to Purchase is linked to the suitability of the site’s user interface as well as the perceived social / technological richness of the website. The results shed light on Digital Millennials’ online shopping preferences and provide guidance to web site designers incorporating Social Shopping or Customization into online shopping applications. Future research will extend the results to other populations, task domains and devices.