Our story began years ago at college in Bloomington, Indiana, when Penny and Dave first met. She was beautiful, free spirited, and lit up every room she entered with her sparkle. Life carried us in different directions—but life and love brought us back together.
In 2025, we got married in Puerto Rico, with the sea as our witness and our hearts set on a "second half" together. Between us, we share three wonderful kids—Maeson, Andi, and Gavin—and two high energy dogs: a Boxer and a French Bulldog, who also happens to be the Boxer's loyal emotional support sidekick.
Dave’s sailing career started when his dad bought a Victoria 18 sailboat. The family story goes he was around the age of nine the day he first felt the play between wind and water. It happened just once but the memory was so vivid that it never left him. That spark grew brighter on the Mississippi River near Nauvoo, Illinois, at Camp Eastman, where he insisted on earning the same Small Boat Sailing merit badge three times before going on to teach hundreds of kids the joy of sailing over six summers. From those riverbanks, he chased the wind across the Texas Gulf Coast, Florida Keys, the Abacos in the Bahamas, St. Vincent & the Grenadines, and both the U.S. and British Virgin Islands. Along the way, he deepened his skills with ASA certifications and even completed the U.S. Coast Guard OUPV coursework “just for fun.” With Pretty Penny, Dave is committed sharing his lifelong love of sailing with every guest who steps aboard.
Penny has completed her ASA 101 (twice) and swears she could handle a man-overboard drill if needed. She’s a licensed nurse, an accomplished event planner, and an interior decorator. Her inner Boho spirit (I didn't say "gypsy") comes alive on Pretty Penny, making the yacht feel casual, comfortable, and full of character. Penny’s touch is what transforms a charter into something more—a place where guests can be fully present, relax into the moment, and create lasting memories.
Together, we created Pretty Penny as more than a charter yacht. It’s about being present, having the courage to chase bucket list items, learning, and making lifelong memories with family and friends.