Flagler's Legacy and Legacy Tours were created by a campus group called SIFE (Students in Free Enterprise). Donna Webb, Executive Director of College Relations, and her campus organization of Students in Free Enterprise saw the potential for a thriving retail business in 1999. SIFE students opened a small shop in the Rotunda during the summer and started selling a few collegiate souvenirs and began charging for guided tours of the College. Their success was so great that the idea for a store in the historic pedestrian shopping district was born. Flagler's Legacy was created with a three-fold objective: to market the College globally, to teach students how to start and run a business and to produce revenue for the College.

Flagler's Legacy opened its door in April 2000, at the north end of St. George Street in a charming 2-story historic building of coquina, stone and aged wooden beams. What started out as a small selection of t-shirts and souvenirs has expanded into a collection of over 300 custom gifts and souvenirs. Over the years, the business has grown to incorporate an online store located on the College's website and another store in the Rotunda, where historical tours of Flagler College are given to over 30,000 guests annually.