The oldest Princess cruise ship is Grand Princess. Unveiled way back in 1998, it's the namesake vessel for the line's Grand class of vessels, which remain at the core of the Princess fleet. There are seven Grand-class vessels in the Princess fleet in all, making it the biggest grouping of ships at the line.

As of 2026, the Grand Princess holds the title of the oldest ship in the Princess Cruises fleet. Launched in 1998, it was once the largest and most expensive passenger ship in the world, debuting the revolutionary "Grand Class" design. While it has been surpassed in size and technology by newer vessels like the Sun Princess and Star Princess (launched in 2024 and 2025 respectively), it remains a beloved fixture of the fleet. Over the years, it has undergone several significant refurbishments to integrate modern amenities like the MedallionClass technology, ensuring that despite its age, it provides a contemporary guest experience. It is a "living legend" within the industry, representing the bridge between the traditional cruising era and the high-tech, mega-ship era of the 21st century.