It’s a long way from Kenya, East Africa to Key West, but it’s a journey businesswoman and local actress Vanessa McCaffrey made … with a few detours.

“I grew up in Kenya, where my mother was an actress,” McCaffrey said from her home in Key West. “She met my father while on the stage in England.”

Jump ahead a few years and a few countries later, McCaffrey is working in the hotel business in Annapolis, Maryland and is involved with the local theater.

“In January 1991, I met the GM of the Reach Hotel in Key West, while working in Annapolis,” she recalled. “I interviewed for the sales manager job and started work in March of that year.”

She credits Shelia Sands, the Reach’s public relations person for showing her around Key West and getting her established in the community.

“I got involved in the local theater quickly,” she said. “And quite by accident.”

That year the Waterfront Playhouse sponsored a summer theater festival called “The New Play Festival and was holding auditions when McCaffrey walked by.

“I was taking my son to Mallory Square for the sunset celebration,” she said. “A woman stood outside the playhouse smoking and out of the blue told me I looked like an actress. I told her she was right and she led me inside to read for the play.”


She got the part in “Author’s Voice” alongside George Gugleotti.

“Here it is all these years later and I’m starring with George again, this time in ‘Moment of Grace’ which opens at the Red Barn Nov. 5,” McCaffrey said, “full circle.”

Since that time in 1991, McCaffrey has been on the stages of the Red Barn, Waterfront Playhouse and the Tennessee Williams Theater. In 1995, she joined the board of the Key West Theater Festival.

“I was on that board for 10 years,” she said. “I stayed until the end.”

Not one able to waste time, McCaffrey turned her hand to writing plays.

“I’ve been working with Tony Konrath and we wrote ‘Easy Come’ together.’”

The duo also wrote the Fringe Theater’s “Bum Farto Play” that was recently performed at the Key West Fire House Museum.

When asked about the differences between theater in Annapolis and Key West, McCaffrey laughed.

“Not as much as you think,” she said. “There are more similarities, really. Both theater communities have talented, dedicated people. The main difference is that in Key West actors are paid. I think the payment makes the actor feel he or she is a professional and it shows in the work. It’s only a stipend, but it’s a big deal.”

McCaffrey has seen changes in local theater since moving to Key West.

“Oh yes! There have been changes,” she said. “The season for theater used to be December to May. Now, the Key West theater only slows down in the summer, but Theater XP, Bob Bowersox’s creation, keeps live theater active all summer.”

Bowersox is also a writer, director and actor in local theater and McCaffrey worked with him last season. The running time of summer plays is only a few performances.

“Summer theater features more edgy plays, ‘Who’s Afraid of Virginia Wolf,’ ‘Stones in His Pocket,’ plays like that,” she said. “They only run for a couple of weekends.”

The reason, McCaffrey said, is the audience in the summer has thinned, even if the talent hasn’t. In season, some of the snowbirds that have homes in Key West are also involved in the theater.

“People that have retire in Key West bring with them skills that theater can use,” she said. “Not just acting, but set design and building.”

In KeyWest, costume design is not the challenge you would think.

“We are fortunate to have some of the best costume designers around in the local drag queens,” McCaffrey said. “Whether it’s an outfit to designing from scratch, or a suit to adjust, we have a talent pool that is fantastic.”

What is her day like now, before the busy season? Busy, she said.

“Bob wrote ‘A Moment of Grace’ that I’m in,” McCaffrey said. “And I’m preparing for rehearsals.”

McCaffrey spends time these days reading and rereading the script for the play.

“What I do, is I read the play over and over,” she said. “When I know the play, I begin to memorize the lines. At first, it’s frightening, seeing all the lines, but in time, especially come rehearsal, I feel comfortable with the other actors. I think everyone has the same concern, ‘Will I remember my lines?’”

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