The Barcolana Regatta is the largest sailing race in the world, attracting over 2,000 boats from all over the globe. This event takes place every October in Trieste, Italy and is free for all to attend. The race starts in the Gulf of Trieste and continues across the Adriatic Sea. The event also includes a variety of cultural and entertainment activities, making it a great choice for budget-conscious travellers looking for a thrilling experience.