Bob quickly became a force in the rapidly growing market for Hawai‘i travel, opening offices on the mainland and marketing Hawaiʻi with a variety of innovative promotional programs. Bob created partnerships that helped build his business. The relationship between MacGregor’s Trade-Wind Tours and the Kelley’s Outrigger Hotels was especially strong and grew stronger as Outrigger built hotels and Bob helped fill them with Trade-Wind customers. At its peak, Trade-Wind Tours became Hawai‘i’s largest wholesaler, accounting for more than 250,000 annual visitors to the islands. In 1959, Trade-Wind Tours merged with Inter-Island Resorts and expanded its operations to include ground transportation and other visitor services.
Bob was a fixture in Honolulu business and social communities. He was one of the founders of the Skål Club of Hawaiʻi and served on many professional organization boards, including the Hawaiʻi Visitors Bureau. When not at work, Bob could often be found playing polo in Mokulēʻia, introducing this sport to residents and visitors alike.
Bob MacGregor and Trade-Wind Tours were a dynamic force that helped Hawaiʻi become a major American travel destination.