Michael Saylor returns to Miami from Bahamas, then heads to DC amid tax case

Michael Saylor flew from Normans Cay Airport in the Bahamas to Miami International Airport on May 11, a 37-minute hop aboard his Bombardier Global Express N3877. The short flight followed a series of island-hopping movements around the Exumas earlier that day, suggesting a brief getaway. The next morning, the same aircraft tracked from Miami to Washington Dulles, returning Saylor to the region at the center of his long-running tax dispute with the District of Columbia.

The return to Washington comes as the D.C. Attorney General’s lawsuit against Saylor — first filed in August 2022 and unsealed that same month — continues to move through Superior Court. The suit alleges Saylor evaded more than $25 million in D.C. income taxes by falsely claiming Florida residency while living primarily in a Georgetown penthouse, citing FAA flight logs of N3877 as evidence of his physical presence in the District [oag.dc.gov](https://oag.dc.gov/release/ag-racine-sues-dc-based-billionaire-michael-saylor). Saylor has maintained that his primary residence is Villa Vecchia in Miami Beach, purchased in 2012.

Saylor’s travel pattern — Bahamas to Miami to Washington in two days — mirrors a familiar rhythm for the billionaire: a quick escape to warmer waters followed by a return to the business and legal obligations that keep his Gulfstream warm. With Strategy Inc. holding over 600,000 Bitcoin and the D.C. case potentially carrying treble damages exceeding $75 million, the stakes for each landing remain high.