An US Navy warship and helicopters are trailing the boat that is believed to be hijacked.
Macay had taken a sabbatical from the Hillsborough based furniture consulting company -- where she worked for more than 30 years -- three years ago to make her journey around the world.
"Adventurous, loved to sail, loved to compete and just one day called me and said, 'John, I'm going to go on sabbatical,'" friend and owner of Profitability Consulting Group John Egger said. "I'm worried sick. I haven't been sleeping well, anybody would be she is such a wonderful person, but she's also very strong, so that gives me hope that somehow she'll come out of this."
Macay said she would be gone a year, but kept extending her trip - living her dream sailing with her friend Robert Riggle. The two had met and joined another couple Scott and Jean Adam on their yacht -The Quest - when they were captured.
"It was great to see she had found a soul mate and it was working," Egger said. "Phyllis was very positive, very excited and according to her route, her flotilla, it didn't look like they were going to anyplace that was real dangerous every place has got the potential but where they're at now, I had no idea they were going there."
Egger says Macay took every safety precaution when she sailed. The yacht was hijacked between Yemen and Somalia -- a haven for pirates. Despite international warships working to protect vessels in the region, pirates have increased in recent years with multimillion dollar ransoms only fueling the trade.
"If anybody has a chance of making it through this, I think Phyllis is that type of person, she's great," Egger said.
Officials say pirates are now holding 30 ships and more than 660 hostages - including the latest kidnapping of the quest.
Macay was keeping an online blog of her trip around the world. To view it, click here