Trump’s Envoy at Sea: Yacht Diplomacy Amid Italy Crisis
VENICE — As diplomatic tensions between U.S. President Donald Trump and Italian Prime Minister Giorgia Meloni reach a boiling point, America’s ambassador to Italy is spending the summer cruising the Mediterranean aboard his personal $450 million superyacht — a floating symbol of the unconventional, and increasingly awkward, state of U.S.-Italy relations.
Tilman J. Fertitta, the billionaire hospitality mogul and Trump donor who serves as U.S. ambassador to Italy and San Marino, arrived in Venice on Friday aboard his 117-meter (384-foot) yacht “Boardwalk” to face hundreds of protesters who clashed with riot police. The scene unfolded as Trump and Meloni traded public insults, and Meloni conspicuously skipped the 250th anniversary celebrations at the U.S. Embassy in Rome.
Protests in the Lagoon
Approximately 300 demonstrators gathered in Venice on Friday to protest Fertitta’s arrival, carrying signs reading “Make America Go Away” and “Venezia non si USA” — a bilingual pun meaning “Venice is not to be used.” According to AP News, protesters briefly clashed with riot police who blocked access to the yacht, with demonstrators yelling “Shame!” at the ambassador, the mayor, and police.
“It’s arrogant to think he can do what he wants in a city that is ever more sold to the single culture of tourism,” organizer Stella Morion told the AP. She said protesters are also opposed to Trump’s international policies, including U.S. strikes on Iran, which she said have caused energy price spikes in Italy.
Italian opposition politicians have also criticized the security operation. Luana Zanella, leader of the Left Alliance in parliament, and Green Party co-spokesperson Angelo Bonelli said in a joint statement that “hundreds of officers across the country — from Palermo to Ravenna, from Catania to Ancona — have been turned into his bodyguards, diverted from their duties to serve as a free escort for the U.S. ambassador’s private vessel.”
The ‘Freedom 250’ Tour
Fertitta’s visit is part of what he calls the “Freedom 250 Coastal Diplomacy” tour, a journey across 13 Italian coastal regions to celebrate the 250th anniversary of American independence. The tour began June 13 from Civitavecchia and is scheduled to continue through mid-August, concluding in Sardinia.
As Deutsche Welle reported, Fertitta has described the initiative as a celebration of “our shared history, our economic partnership, and the cultural bonds that make the U.S.-Italy relationship so special.” He is expected to attend Venice’s Festa del Redentore on Saturday, a centuries-old festival commemorating the end of the plague in 1576.
The yacht itself — a six-story vessel featuring two helipads, two swimming pools, and a fully equipped spa and gym — has drawn particular ire. Protesters noted that at 117 meters, it towered over neighboring historic buildings. On July 4, activists unfurled a banner as long as the yacht to illustrate what they called “the dimensions of his arrogance.”
A Billionaire Ambassador
Fertitta, with a net worth of $11.3 billion according to Forbes, is a longtime Republican donor who built his fortune through Landry’s restaurants, hotels, and casinos. He also owns the NBA’s Houston Rockets and holds a significant stake in Wynn Resorts. In late May, Fertitta Entertainment announced it would acquire Caesars Entertainment in a deal valued at approximately $17.6 billion, as Fortune reported.
Nominated by President-elect Trump on December 21, 2024, and confirmed by the Senate on April 29, 2025, in an 83-14 vote, Fertitta is part of a broader pattern of Trump appointing billionaire donors to key diplomatic posts in Europe. Political analyst Giovanni Orsina of Rome’s Luiss University told the AP that an ambassador using his own yacht for “traveling diplomacy” is “pretty unusual” — one that “can be perceived negatively, on the one hand, but it also can be taken as a sign of attention toward the country.”
Trump vs. Meloni: A Fractured Alliance
The yacht tour comes at a particularly delicate moment for U.S.-Italy relations. The once-warm relationship between Trump and Meloni — two right-wing populist leaders who shared views on immigration and national sovereignty — has deteriorated sharply in recent months.
As The Guardian reported, Trump claimed during an interview with Italian television that Meloni “begged” him for a photo at the G7 summit in France. Meloni responded in a video statement, saying Trump “totally invented” the story and that “Italy and I never beg.” Trump has continued attacking Meloni on social media, at one point suggesting a “restraining order” was needed against the Italian leader.
A major source of tension is the U.S. war with Iran. Italy denied U.S. aircraft permission to land at Italian bases, a decision Meloni defended as a matter of protecting national sovereignty. Trump accused her of lacking courage. Meloni did not attend the 250th anniversary celebrations at the U.S. Embassy, and Secretary of State Marco Rubio reportedly visited Rome in May to try to “thaw” relations.
What It Means
The image of a billionaire ambassador literally at sea — both physically and metaphorically — while the two leaders trade insults is deeply embarrassing for U.S.-Italy relations. Italy is a key NATO ally hosting several U.S. military bases, and the rift could have lasting effects on defense, trade, and migration cooperation.
For Venice, the protests tap into broader Italian frustration with overtourism and the commercialization of historic cities. Many of the same activist networks that protested Jeff Bezos’s wedding in Venice last year mobilized against Fertitta’s arrival.
Fertitta, for his part, has declined interview requests but issued a statement supporting the right to peaceful protest. “Coastal Diplomacy celebrates our nation’s founding and these fundamental rights,” he said.
Whether his unconventional approach to diplomacy ultimately strengthens or further strains the U.S.-Italy relationship remains an open question — one that, for now, finds America’s man in Italy drifting somewhere between the two.