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Outriggers Charter Fishing
Captain Ryan Rolland

Ryan Rolland

Founder/Captain

About Captain Ryan

Ohio-born and bred, Ryan’s childhood declaration of becoming a Florida fisherman excited his mom. He practically grew up with a rod in hand, perfecting his angling in local ponds and lakes. At 18, he bolted to Florida, hustling odd jobs until he snagged a role on the Flying Fish, rocketing to captain status in ’98.

Since then, Ryan’s leveled up to a 100 Ton Masters Captain. In 2004, he seized the opportunity to start Outriggers Sports Fishing Charters, and it’s been full throttle ever since. He’s poured everything into the business, turning dreams into reel-life adventures.

Testimonials

Eric Betts
Eric Betts
June 2, 2024
**Outstanding Review of Outriggers Sports Fishing Charter** I recently had the pleasure of experiencing a fishing trip with Outriggers Sports Fishing Charter for a bachelor party, and it was an adventure to remember! From start to finish, Captain Ryan and his first mate, Tom, provided an exceptional experience that exceeded all our expectations. Captain Ryan and Tom were not only super friendly but also incredibly knowledgeable and experienced. They made everyone feel welcome and comfortable, and their passion for fishing was infectious. They went above and beyond to accommodate the bachelor, making sure he had an unforgettable time. The highlight of our trip was the incredible fishing. We primarily caught grouper and snapper, both of which provided exciting challenges and delicious rewards. The ultimate thrill came when we reeled in - and released - a massive 300-lb Goliath Grouper! It was a breathtaking experience and a story we'll be sharing for years. The boat was well-equipped, clean, and perfectly suited for our group. Captain Ryan's expertise in navigating the waters and Tom's assistance ensured that we had the best possible chance of catching fish. Their teamwork and dedication to our enjoyment were evident throughout the trip. Overall, Outriggers Sports Fishing Charter delivered an outstanding fishing adventure. If you're looking for a top-notch charter with a fantastic crew, look no further than Captain Ryan and Tom. They will make your fishing trip an unforgettable experience. Highly recommended!
kyle gerst
kyle gerst
June 2, 2024
Awesome day! Very successful trip and the guys took great care of us.
Sean Betts
Sean Betts
June 2, 2024
1st class fishing with 1st class crew. Thanks again for the amazing memories.
Justin Jasper
Justin Jasper
June 2, 2024
Ryan and Tom were super friendly and knowledgeable. We caught fish at every location and caught more than we anticipated. Cannot wait to come back!
Dan Wiggins
Dan Wiggins
June 1, 2024
Had an awesome trip with Outriggers Charters out of Marina Jacks in Sarasota today. Captain Ryan and Tom were awesome and we will definitely be back. “Hook Em Danno”
Erin Tipton
Erin Tipton
May 31, 2024
Awesome experience with Ryan and Tom! They had us on fish immediately and took care of us every second of the day. 10/10 recommend fishing with them!
Brian Sewell
Brian Sewell
May 28, 2024
When everyone else is just fishing, with Captain Ryan you will catch and bring home the most precious proteins on the planet. Whether you go for Ajs, Red snapper, or Groupers no one works harder for you then this company and various mates. The professionalism shines through with passion for the sea. I want to fish with Outriggers every time I'm in Florida.
Wayne Bersch
Wayne Bersch
May 20, 2024
Capt. Ryan and First Mate Tom showed us how to have fun in the Gulf! Lots of snapper and a grouper for that night’s dinner. They filleted our catch and bagged them for us. These are good old boys who know what they’re doing and know how to laugh. We here in expert hands and ended the trip with memories and smiles. They also have an excellent online booking system. Find a time slot, book it and you’re gold.
lori ann blau
lori ann blau
May 8, 2024
Great boat, awesome crew, caught 34 fish, loved the music. What can I say?

Book Your Adventure

Wanna catch fish and have a great time doing it? Book your deep-sea fishing trip today!