There is a series of open water swims in Sicily near or in the Strait of Messina held annually in August and September. The Strait of Messina is a narrow channel between the eastern tip of Sicily and the southern tip of Calabria (see map below) which is on the Italian mainland.
The first race is the 5.2K 45th annual Traversata dello Stretto with the longest history and a difficult course across the Strait of Messina. First crossed in 1930, the Strait has strong currents and natural whirlpools that make for a challenging and enjoyable event to do and watch, especially on a clear day. The Traversata dello Stretto starts at Torre Faro, crosses the Strait of Messina to a turn in Cannitello in Calabria on the Italian mainland, then traverses along the Italian coast and finished in Villa San Giovanni.
The second race is the 10th annual Trofeo Baia di Grotta (see finish point on left). The third race is the 1.8K II Trofeo Onda Azzurra along the Calabria coast. The fourth race is 36th annual 3.7K Favazzina-Scilla swim in late August. The fifth race is the 5.1K XI Memoria Nino Sofi. The sixth race is the 3K Città di Reggio Calabria II in September.
Photo of the Traversata dello Stretto race courtesy of Nino Fazio