ADVENTURE
RUNS DEEP
DeepEnd Charters was built on a simple idea: the best days in Key West happen offshore.
What started as a passion for fishing and life on the water has grown into a charter experience centered around authenticity, skill, and genuine connection.
Every trip reflects a deep respect for the ocean and a commitment to giving guests more than just a day out, it’s about the stories you’ll tell long after you’re back on shore. With local knowledge, experienced captains, and a laid-back Key West spirit, DeepEnd Charters invites you to experience the water the way we know and love it.
Every mile offshore is earned.
Every trip carries meaning.
Captain Jake
Captain Jake built his life around the ocean. After getting his start aboard the Tortuga in Key West, he developed a deep understanding of offshore fishing and the waters of the Keys. Eager to go farther, he began running his own trips on a 34’ SeaVee, chasing bigger fish and expanding beyond the reef.
Driven to reach the deep-water grounds few boats touch, Jake set his sights on a Freeman — built for long runs, comfort, and serious offshore fishing. Over more than a decade, he built a reputation for his skill, patience, and willingness to teach, sharing his passion with everyone who stepped aboard.
Respected by fellow captains and trusted by his clients, Jake’s legacy lives on through every trip we run, carrying forward the knowledge, dedication, and love for the ocean that defined him.
Captain David “Dave” Sivley
Captain David “Dave” Sivley has called the Florida Keys home for over 20 years, building his life around offshore fishing and the waters that define it.
His experience spans some of the world’s top big-game fisheries, including time in New Zealand and Australia targeting marlin, followed by a season in Costa Rica refining his billfish techniques and offshore strategy. After returning to the Keys, he ran a successful charter business, What’s Kraken, for four years, earning a strong reputation in a competitive market.
For the past several years, Dave has fished alongside Jake Harnett with DeepEnd, helping shape offshore programs built on preparation, precision, and passion for the ocean. Today, he brings that experience to the Gulf and South Atlantic, running trips focused on quality fishing, strong teamwork, and creating lasting memories on the water.
Rooted in the Community. Built on Family, Tradition & Giving Back.
Deep End Fishing Charters was built on more than a love for the water, it was built on community.
Captain Jake was known throughout the Keys for always showing up when someone needed help, supporting local businesses, and giving back whenever he could. From coaching and sponsoring Little League baseball teams to taking kids on unforgettable sandbar trips, Jake created experiences that many local families still talk about today.
In his honor, Deep End proudly sponsored two Little League teams this season, one for Tiffanies’s son and one for Captain Dave’s son, with Captain Dave continuing the tradition as an assistant coach. Every year, the team would pile onto the boats for a sandbar bonding trip, giving many kids their very first day out on the water, moments filled with excitement, laughter, and memories that last a lifetime.
Jake believed in supporting local whenever possible, whether it was buying rods from Esky Rods, grabbing hot sauce from Harpoon Harry’s, or recommending Dolphin Deli as his favorite place to eat. That same community-first spirit continues today with Captain Dave and the entire Deep End family.
