Jamie Simmons Travel & Adventure

An avid pilot and sailor, Jamie Simmons has a taste for adventure! He’s also well on his way to having visited all 50 of the United States.

Throughout his life, Jamie Simmons has lived in numerous states.  His career has certainly taken him across the country.  He’s lived in New Hampshire, Alaska and Georgia — just to name a few!  Now, he’s interested in marking off his map of the United States by visiting all 50 states.  An avid sailor and licensed pilot, Simmons looks forward to sailing through and flying over the country.  In his view, there’s no better way to admire an area than from in the water or up above in the air!  Simmons looks forward to mapping out an adventure around the US in the near future.

Sailingmonohull sailboat

For nearly two decades, Jamie Simmons has sailed monohull sailboats.  He’s dabbled in a variety of options, having navigated waters on everything from Pearson 29s to Swan 45s.  For Simmons, manning a sailboat is equal parts adventure and relaxation.  He thoroughly enjoys the opportunity to appreciate some of the most gorgeous bodies of water the US has to offer.  But sailing isn’t always a leisurely glide down the lazy river.  An entrepreneur at heart, Simmons loves taking on a challenge — and his pursuits in sailing are no exception!  Navigating the tough terrain of stormy waters is as exciting for Simmons as it is challenging.


At 40 years old, Jamie Simmons geared up for his pilot’s license.  This would spark what would prove to be one of his life’s greatest passions.  To this day, he finds fulfillment in the incredible adventure of flying his own plane.  A born leader, taking on the role of a navigator certainly isn’t a challenge Simmons would ever shy away from.  A unique hobby, flying is no small feat.  The process certainly fits right in with Simmons’s lean towards unique and exciting challenges.  His goal as a pilot is to one day fly seaplanes down to the Caribbean, just like acclaimed country music star and revered businessman, Jimmy Buffet.