The modern leisure cruise industry is one of the most dynamic and profitable sectors of the global tourism industry. However, the cruise industry has entered a maturity stage in North America, the largest cruise market in the world, as growth of the new-to-cruise segment diminishes. Industry analysts emphasize that cruise lines need to not only attract new customers, but also to motivate existing ones to repurchase. Achieving these dual goals demands a better understanding of the differences between these market segments. This study used proprietary reservation data containing more than one million individual records of cruisers’ demographic and behavioral information. Analysis showed that compared with new cruisers, repeat cruisers to a cruise brand are less price sensitive, live closer to embarking ports, are more likely to choose longer cruises and better cabin types, and to book cruises further out from the sailing date; in addition, there are notable behavioral differences between first-time and multi-time repeat cruisers.