Michael Saylor's jet lands in Miami the week of his Bitcoin treasury milestone

Recent flight data shows the aircraft has been unusually active this month, with a September 13 leg from Ibiza to Washington Dulles, followed by a same-day hop to Teterboro, and then the September 14 shuttle to Miami. That pattern suggests a return from a European sojourn — the jet had also flown from Munich to Ibiza on September 11 — before settling into a DC-to-New York-to-Miami rhythm that matches Michael Saylor's known travel habits. The aircraft is registered to 821 393 LLC at Strategy's headquarters, a structure that has drawn scrutiny in the DC Attorney General's ongoing tax lawsuit, which alleges Saylor evaded more than $25 million in District income taxes from 2005 to 2020, citing FAA records of this very jet as evidence of physical presence.

For Michael Saylor, the Miami landing is less a departure than a return. He has long claimed Villa Vecchia, an 18,000-square-foot Miami Beach estate purchased in 2012, as his primary residence, even as the DC AG's office contends he actually lives at Trigate, a Georgetown penthouse assembled from three units. The aircraft's frequent shuttles between Dulles, Teterboro, and Miami — with occasional forays to Aspen, San Diego, and Farnborough — sketch a life split between the regulatory battleground of Washington and the crypto-friendly shores of Florida. If aboard, this flight would be another stitch in that pattern, a quiet repositioning ahead of a week of shareholder votes and policy chatter.

The jet's owner also tracks a 45-meter Feadship yacht, Harle, which as of a fix logged nine minutes ago was at rest in the Ligurian Sea, some 4,000 nautical miles from Miami. But with the vessel parked off the Italian coast, it offers no explanation for this particular crossing — just a reminder that Michael Saylor's movements, like his Bitcoin ledger, are never quite as simple as a single flight plan.