With a goal of simplifying the yacht experience and making leisure time carefree, Superyacht owner Michael Saylor founded Fleet Miami in 2014. According to Saylor, "After owning and chartering my own boats, I saw a way to advance the cause of yachting. Fleet Miami is a manifestation of my desire to not see empty boats. Unused boats are not cost effective, and there is something very sad about them. I feel I have come up with a practical, equitable solution for a certain type of yacht owner and yacht enthusiast that will enhance the joy of yachting.”

147 HarleMembership in Fleet Miami allows members to buy into a fleet of yachts without the cost of ownership, but with more flexibility than charter memberships. Cancellations and rain dates are allowed. As Saylor states, "Fleet Miami operate as a cooperative and do not have a conventional charter contract. Let’s say you book a charter in the Bahamas and it rains for four of your seven days. We would be sympathetic to that and give you a rebate or a rain check to take those days. Or what if your son breaks his leg the day before a charter and you can’t make it? We are forgiving. We understand stuff happens, and you’ll be able to take that charter another time."

Three level of memberships are available, ranging in cost from $250,000 to $1 million. Membership does not expire, and is refundable at any time. The differentiating factor in the memberships is the amount of credits offered.

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Fleet Miami boats are all crewed by Fleet Miami staff, and the crew is included in the membership. Itineraries are all custom developed for the member. The current fleet includes the following, although it is consistantly growing.

Miami. Florida

  • 87’ Warren M/Y Mystique,
  • 54’ Eastbay M/Y Shredder
  • 36’ Custom Water Shuttle Washington, DC
  • 87’ Warren M/Y Moksha
  • 68’ Azimut M/Y Firefly Stamford, Connecticut
  • 87’ Warren M/Y Andiamo


New England / Miami / Bahamas

  • 154’ Delta M/Y Usher with her chase boat 68’ Hampton M/Y Splinter

Mediterranean / Caribbean

  • 147’ Feadship M/Y Harle

Members can reserve a yacht months in advance, or call the day before for an unplanned escape, or sudden great day for cruising.