Skift recently referenced Classic Vacations in an earnings story about its new owner. I somehow missed that the company had been acquired (again) in late 2025, and seeing the name sent me down memory lane.
One of the first acquisition projects I was ever involved in was Classic Vacations (then known as Classic Custom Vacations). It was the early days of online travel, when everyone was trying to figure out how to bring traditional travel companies into the digital world.
It was my first real exposure to acquisition due diligence. On day one, all the VPs, SVPs, and C-suite folks from the potential acquiring company I worked for were on site. After a couple of days, they disappeared. And there I was, a lowly manager, rolling up my sleeves to actually understand how the business operated.
The legendary Ron Letterman, founder and CEO of Classic Custom Vacations, spotted me in the office and invited me to lunch. He skipped the pleasantries. He questioned the deal, the strategy, and whether the folks circling the company really understood what they were buying. He unloaded. I was shell-shocked, but I never forgot that conversation.
We passed on the deal. Expedia didn’t.
In 2002, Expedia acquired Classic Custom Vacations for roughly $48 million. Years later, I heard some at Expedia referred to it as “their Vietnam” (the war, not the tourist destination). Running a high-touch wholesale business built on advisor relationships, faxes, and operational complexity was very different from scaling an online OTA.
Expedia eventually sold Classic in 2021 to The Najafi Companies. Now TBO has acquired the company for $125 million.
TBO is a Gurugram, India-based B2B travel distribution platform, publicly traded in India, focused on serving travel advisors and agents globally with air, hotel, and ancillary inventory. Not a household name in Hawaiʻi, but clearly a serious player in the global agency ecosystem.
The fact that TBO sees value in a nearly five-decade-old luxury wholesaler says something. Classic still works with more than 10,000 travel advisors and maintains deep supplier relationships across Hawaiʻi, Mexico, the Caribbean, and Europe.
Turns out Ron was right during that lunch so many years ago. It was never as plug-and-play as the acquirers thought. Maybe now it has found a more understanding home at TBO.
