Da Porto a Porto

The waters encircling the Monte Argentario promontory were not always this continuous expanse of Tyrrhenian blue. Once an isolated island, the landscape shifted over centuries as complex interactions between sea currents and the Albegna River deposited vast amounts of sediment, creating the dual sandbars known as the tomboli of Giannella and Feniglia. This geological evolution effectively anchored the massif to the mainland, defining the coastal profile that swimmers navigate today. The water here is part of the Pelagos Sanctuary, a protected marine environment where sightings of dolphins or turtles are not mere folklore but documented occurrences managed by local conservationists.

A path through history

As you round the promontory on the 22km course, the shoreline serves as a silent chronicle of the Mediterranean’s turbulent past. Shortly after departing from Porto Ercole, the imposing silhouette of the Forte Filippo appears. Built in 1558 by the Spanish, the complex’s double curtain walls and deep moats were engineered to render the bay impenetrable to hostile naval forces. This strategic importance was tested violently on 14 June 1646, during the Battle of Orbetello. In a display of tactical improvisation, French and Spanish fleets engaged in a chaotic fight where sailing ships were physically towed by galleys to maneuver through the light summer breezes. Further along the route, the maritime history takes a more somber turn near the coves where the painter Caravaggio spent his final, fevered days in 1610, leaving behind an artistic legacy that haunts these waters.

Navigating toward the finish at Porto Santo Stefano, the architecture shifts from military to defensive observation. You will pass beneath the Torre di Lividonia, a mid-16th-century watchtower originally commissioned to alert the coast of approaching Barbary pirate raids, a threat that remained active even into the early 19th century. The Da Porto a Porto event, now in its 9th edition, transforms this historical geography into a 22km journey of solidarity. Organized by the Polisportiva Amatori Prato, the race is a significant annual fixture held on August 10th. The logistical complexity of managing such a lengthy coastal crossing, including the coordination of escort boats to ensure safety along the exposed headlands, is supported by local maritime volunteers, ensuring that every stroke contributes to the ongoing fundraising efforts for the Associazione Tumori Toscana.