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Jonathan Kaplan is a professional Jack Sparrow impersonator and pirate entertainer based in historic St. Augustine, Florida. For over 19 years he's brought the character to life with a movie-accurate costume, spot-on voice, and that signature swagger.
Perfect for birthdays, weddings, bachelor and bachelorette parties, corporate events, and festivals. Jack mixes and mingles in character, poses for photos, and makes it feel like the real thing just crashed the party in pirate style!
Add-ons include:
Giveaway treasures,
Pirate Story Time,
Personalized videos.
Additional Pirate Crew
He can even officiate weddings!
Serving St. Augustine, Jacksonville, Orlando, and statewide travel. Savvy?
6 reviews
Chelsea U.
July 31, 2026He brought the fun
Hired as: Pirate Entertainment
Nancy M.
July 7, 2026It was perfect!!! The renewal went wonderfully perfect. He was so in character during the ceremony and on the Fury cruise. Everyone loved him! Definitely use him again!
Hired as: Pirate Entertainment, Wedding Officiant
Lisa S.
July 6, 2026🏴☠️ Jonathan Kaplan absolutely nailed Jack Sparrow! From the voice and mannerisms to the hilarious wit and pirate swagger, he had everyone laughing and completely entertained. It truly felt like Captain Jack had stepped right out of the movies! Thank you for making the event so much fun and unforgettable. Highly recommend if you’re looking for an incredible Jack Sparrow experience! ⚓️🏴☠️
Hired as: Pirate Entertainment
Megan S.
May 31, 2026Very authentic and added some spice to our pirate party!!
Hired as: Pirate Entertainment
Zack W.
March 23, 2026Thank you Captain Jack!
Awesome guy and he’s the real deal!
Hung out with my party and totally made the entire weekend. We will be talking about this forever! Thank you so much. We will see you in the future for sure!
Hired as: Johnny Depp Impersonator, Look-Alike
Price range: Starts at $175 per hour
Languages: English
Gig length: 30 - 240 minutes
From planning through the party, you'll get a partner who wants the details that make the night land. Before the date, we'll talk through guest mix, vibe, timing, and any moments you want Jack woven into, like a grand entrance, cake, gifts, or photos with the guest of honor. Once that's set, he shows up ready and stays fully in character for the whole booking.
Picture this: guests are chatting, then Jack Sparrow walks in like he owns the place. Within minutes he's working the room, posing for photos, tossing out one-liners, and making people forget it's a regular party. Movie-accurate look and voice, warm with every age, and flexible enough to play along with your plan without turning it into a stiff stage act.
It's the real swagger, up close, authentic, always leaving smiles and legendary memories.
Jonathan Kaplan is a Jack Sparrow impersonator based in historic St. Augustine, Florida. He has been bringing Captain Jack to life at events across the country since 2005.
What began as a love of Pirates of the Caribbean turned into more than 18 years of work on the look, the voice, and the swagger.
His dedication to the character earned him a feature on the At World’s End DVD, a stage with original cast members, and a meeting with Pirates of the Caribbean composer Hans Zimmer.
Jonathan Kaplan is an independent tribute performer and is not affiliated with, endorsed by, or sponsored by Disney, Jerry Bruckheimer, Johnny Depp, or any related entities.
Needs vary by event. Specific requirements will be confirmed for your booking. The following are general requirements to keep in mind.
Arrival: Usually arrives already in full costume. For longer travel, he may request a private changing room. For select events he may bring along a character handler / assistant (Confirmed during booking process)
On site: Please provide water and a shaded or indoor break area. Plan for short breaks of about 5 to 10 minutes each hour, especially outdoors. For large outdoor events, shade is required.
Photos: Happy to be photographed during the event. Images may be used for Kaplan Sparrow promotional purposes unless you request otherwise.
Thursday
Cocktail Party
5:30pm - 6:30pm
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St Augustine, FL
Monday
Wedding Ceremony
11:00am - 11:30am
•
St Augustine, FL
Saturday
Retirement Party
6:00pm - 8:00pm
•
Jacksonville, FL
Saturday
Children’s Birthday Party
2:00pm - 3:30pm
•
Ponte Vedra Beach, FL
Saturday
House Party
11:00pm - 12:30am (Sun)
•
St Augustine, FL
Saturday
Halloween Party
8:00pm - 10:00pm
•
Jacksonville, FL
Saturday
Birthday Party
7:00pm - 7:15pm
•
St Augustine, FL
Pirate Entertainment