Flagler's Legacy and Legacy Tours were created by a campus group called SIFE (Students in Free Enterprise). Donna Webb, Executiver Director of College Relations, and her campus organization of Students in Free Enterprise saw the potential for a thriving retail business in 1999 when SIFE students opened a small shop in the Rotunda during the summer and started selling a few collegiate souvenirs and also started 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 on-line 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 annual.