The Ruff Riders Sailboat Race is another fun filled South Padre Island Labor Day Weekend icon. The race usually begins at the windsurfing area just north of the SPI Convention Center, follows the bay under the causeway, turns east out the jetties & then north in The Gulf of Mexico to the Port Mansfield cut, through the cut and then back to the origination point. The race, although fun filled, is a serious sailing enthusiast race. It's a long journey to go all the way around South Padre Island so the race is divided into 2 days with a predetermined over night stop over point up the beautiful South Padre Island beach. Come & compete or just enjoy watching the colorful sailboats vie for position.