Shane Hale and his pup Harley set sail on Saturday, but the weather soon turned nasty and a storm set in.
In the waters off Sarasota County, Florida, in the US, the pair were headed for Florida Keys and across the Caribbean, until the storm became too powerful and Harley fell overboard.
“It was throwing me off the boat, slamming me back on the boat, throwing me off the boat, slamming me back on the boat,” Mr Hale told WFLA news.
“I could see his head bobbing behind the boat, the swells, I don’t want to seem like an exaggerating kind of guy, but I think they were nearly [three metre] swells.”
Footage from before the storm shared to Facebook shows both Mr Hale and his pet were wearing a tether and life jacket onboard.
“I got to his tether and when I pulled the tether, I realised there wasn’t enough weight on the end of that tether for a dog to be on there. Sure enough I pull it out and I just see his life jacket,” he said.
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“I laid there for the rest of the storm and I prayed for Harley, and I prayed for me,” he said.
Mr Hale didn’t expect to see his best mate alive again.
“When he went off the boat and I see the way he went, I never in a million years expected to see my dog again.”
When Mr Hale arrived at shore, he shared a plea for help to find Harley.
The following morning, the sailor received a phone call, with news he described as a “miracle”.
Harley had somehow battled the choppy waters and swam almost five kilometres to a nearby beach, where he was found.
Vets reportedly said the sea dog had a slight case of pneumonia, but is expected to make a full recovery.
Meanwhile Mr Hale has vowed to put his sailing days behind him and embrace a land-locked life with his clever mate.