But in murky Camden, North Carolina waters beside the boat that was supposed to be his new beginning, the Lamb's Marina Dockmaster found Calabrese's lifeless body.
Authorities will only say they're treating it as a suspicious death.
Arnold Parkinson says Calabrese had been at the Marina less than a month.
Monday, they noticed he was missing when they found his cat wandering the marina.
Thursday morning, Parkinson saw something in the water.
“I thought at first it was a dead otter or something like that, but with another look it dawned on me that it was Michael,” says Parkinson.
The dockmaster says he found Calabrese's body at the front of the boat; he was floating vertically and he could see the top of his head."
We came to know Calabrese during Hurricane Irene.
He and his girlfriend set sail during the storm but got stuck on the beach in Ocean View.
Soon after, he landed in jail for trespassing at a city shelter.
It's where he talked to us for the first time.
Days later someone set his boat on fire.
Police still haven't figured out who or why.
In December after someone bought Calabrese a new boat, he told us he nearly ended it all after the storm.
Calabrese said he battled alcohol and depression.
But when NewsChannel 3 last spoke with him, he was excited about writing his new book, getting back on the water and setting sail for a better tomorrow.
For Calabrese, sadly, his silver lining didn't last very long.