There's always the over-engineered approach.
If the mast is bare, you could roll it back until it tips toward the rear, then walk if back from the ground until it reaches the roller, at which point you have to get back on the boat to lift the top off the roller and pass it over the side. Or put the base on a dolly (might need to fix it so it stays on the dolly) so you can walk it back on pavement from up on the boat.
I hang mine off the garage ceiling on the diagonal when I travel without it.
I added a hole in the bridge (connector) section of my Dowsar full enclosure so I can carry the mast on the boat with the canvas up.
The bridge clearance in that position is around 11 ft or so, as I can sneak under the Fairport (NY) Erie Canal lift bridge in the normal* down position, which is 6 ft at the low end, and with a 4% grade over 139 span, it's another 5-1/2 ft higher at the south end. The photo above was taken with that bridge just off the bow, in fact.
https://en.wikipedia.org/wiki/Fairport_Lift_Bridge
*Fun fact - when it was built, the normal position was UP. There was a ton of barge traffic, and very little pedestrian traffic and even less horse and/or carriage traffic, so it was built with elevated stairways that allowed folks to cross the bridge on foot with it up. And you still can. They just shoo you off before they lower it. I believe most or all of the old lift bridges on the canal were made that way.