This high profile project evaluated alignment alternatives for extending the popular Friendship/Gandy Bridge Trail to link with the community and neighborhoods on the east side of Tampa Bay. The project also addressed: the difficult crossing of Gandy Boulevard in South Tampa; a new drainage system for the trail; and designs for safer motorist and pathway user interactions. After environmental impact and permit requirements were assessed, focused roadway crossing adjustments and trail drainage designs were evaluated for improved function and safety. Roadway crossings analyzed include: a pedestrian/bicycle overpass, an at-grade crossing, boardwalks over the bay, and an under-crossing of the existing roadway bridge. The under-crossing was selected as the preferred alignment, functioning with a special baffled drainage system to keep bay and rain water off the surface of the trail. Cost estimates and reviews of development options were conducted by Landis Evans + Partners, formerly Sprinkle Consulting, to ensure construction efficiency. The completed concept layout allows for more convenient and efficient use of the Friendship Trail. New roadway crossings have been designed to direct pedestrian and vehicle traffic in a mutually beneficial and safe way for many years to come.