Sailing San Diego to Cabo San Lucas. The event begins every year at the end of October. Nearly 2,500 boats have done the event so far, with roughly 9,000 participants aboard. The distance is Approximately 750 miles with two stops along the way. The goals of the Ha-Ha are simple: for everyone to get to Cabo safely while enjoying some great sailing and making countless new friends. The event is open to all boats over 27 feet that were designed, built and have been maintained for open ocean sailing.

Regata del Sol al Sol is an open ocean sailboat race regatta in the Gulf of Mexico from St. Petersburg, Florida to Isla Mujeres, Mexico.