Photo courtesy Steve Robinson
Photo courtesy Steve Robinson


Welcome to Into the Skinny Charters!

Based in Islamorada, Florida, we are boasted as the Sport Fishing Capital of the World.  Whether we fish the crystal clear ocean-side flats or the shallow back country waters of Everglades National Park, our day with will be fun and filled with fish…  My ultimate goal is to share with you the natural beauty of this unique ecosystem and catch some amazing fish!


Winning Fishing Awards in Islamorada
Captain Jacob and Luca winning back to back years


Meet The Captain

I am Captain Jacob Hill, and I would love to take you fishing!  I love fishing!!  It is my greatest passion in life, and I want to share it with you!  I was born in Des Moines, Iowa in 1986 to two Iowa natives.  At the age of three, we moved from the Twin Cities area of Minnesota to Jacksonville, Florida.  From there is where my love of fishing began.  My earliest memories are fishing at the lake in our neighborhood in Jacksonville.  I learned how to catch Blue Gill and then use them as bait to catch big ole large mouths.  While the other kids wanted to play other games, I simply wanted to fish…  We later moved to the Tampa Bay area of Florida when I was a young teenager.  It was there that I was exposed to artificial bass fishing as well as the inshore fishing on the gulf coast.  I was forever changed.  Clear water and big fish – so much fun. There was nothing like sight casting to tailing Redfish, or hooking a big Snook.

Through college and my 20’s I began to explore fishing in the Keys.  I learned these waters through trial and error, and on my own accord.  The draw for me was the gin-like clear water, and the species of fish that they held, like Bonefish, Permit, and Tarpon.  Considered the big three and the most challenging sight fishing on the planet.  Nothing compares to the hunt or the blistering battles these fish put on.  So, in 2011 I quit my “office” job and moved to Islamorada to pursue my dreams of becoming a fishing guide.  The sight fishing opportunities that the Keys and Everglades National Park offer are world class.  Not to mention, it is one of the most beautiful and unique ecosystems on the planet.  I enjoy catching fish, however I truly enjoy sharing this experience with others.  While most guides avoid the water on their off days, I take to it as much as possible.   I look forward to our day on the water together.


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Please reach out to let me know any questions you have about fishing with me.

Contact Me, Captain Jacob