Flyin' High Charters · Sugarloaf Key, FL
Fly fish the Florida Keys with Capt. Jesse Register
Tarpon, permit, and bonefish on the flats and in the backcountry from Big Pine to Key West, and everything in between.
- Rated 5.0 by anglers
5.0- Trips from
- $600 half day
- Anglers
- 1 to 2 per boat, all skill levels
Fishing out of a 2023 Maverick HPX-V II with G. Loomis rods and Tibor reels
Your guide
Capt. Jess Register
Traded a corporate job for the poling platform.
I grew up fishing Florida's east coast in New Smyrna Beach. Once I picked up a fly rod, it stopped being a hobby. I left a corporate job to chase a life on the water, and I've guided full time in the Keys for seven seasons now.
The best part of my day is the moment an angler connects with a fish they've been chasing for years. First trip or fiftieth, I build every day around what you want out of it.
- Home water
- Sugarloaf & Big Pine Key
- Skiff
- 2023 Maverick HPX-V II, 70 HP Yamaha
- Tackle
- G. Loomis rods, Tibor reels
- Trips
- Half, three-quarter, and full days
Target species
The Keys grand slam
Tarpon, permit, and bonefish in a single day is the trip anglers talk about for years. Each fish asks for something different: power for tarpon, precision for permit, stealth for bonefish.
-
The Silver King
Tarpon
Year-round, migration peaks Apr to Jun
Resident fish all year and migrating giants over 100 pounds each spring, sight cast on oceanside flats. Raw power from the eat to the last jump.
Tarpon trips -
The Holy Grail
Permit
Year-round, best spring and Jul to Oct
Cautious, picky, and unforgettable once one finally eats. The fish that keeps fly anglers coming back.
Permit trips -
The Ghost of the Flats
Bonefish
Year-round, best spring to fall
Fast, technical, and spooky in skinny water. Bonefish reward a quiet approach and a clean presentation.
Bonefish trips
Lower Keys season chart
Plan your trip around the fish
What's running, month by month. Pick a month to see what we'd target and ask for those dates.
Trips
Built around the tide, not the clock
Every charter is planned around the tides and wind on your dates, and what you want out of the day. Chasing one trophy or keeping a rod bent, we fish the water that gives you the best shot.
Fly Fishing
Sight casting from the bow to tarpon, permit, and bonefish, with coaching on every shot. Built for your skill level and casting style.
Fly fishing trips
Backcountry
Protected mangrove water for baby tarpon, snook, and jacks. Steady action when the wind blows.
Backcountry tripsNot sure which trip fits?
Tell Capt. Jess your dates and what you want out of the day. He'll match the trip to the tides, the wind, and your experience.
Ask Capt. Jess
Rates
One or two anglers. Rods, reels, flies, tackle, ice, and water are on the boat.
- Half day 4 hours $600
- Three-quarter day 6 hours $700
- Full day 8 hours $900
From the boat
Anglers who keep coming back
I’ve been fishing with Jess for about 15 years now. I followed him down from Boca Grande to the FL keys and have had countless awesome days on his skiff!
Google review★★★★★He finds fish and big fish… Clear, concise and calm instructions that end in hookups. An absolute pro.
Google review★★★★★
14 reviews on Google
- ★★★★★
We have fished with Jesse 5 times, heading back next year for trip #6. I was a fishing guide in Alaska so I can spot a good guide when I see one, and Jesse is one of the best! My wife and I love going with him because he doesn’t have the typical attitude that has come to be expected from Salt Water guides. He is the only guide my wife enjoys going with because of his personality, attitude, and the dude finds fish! I highly recommend going with Jesse if you want to catch big fish and have a great time.
Eric SumpterGoogle review · Dec 2025 - ★★★★★
Capt Jess puts you on the fish. His tackle is top notch and his vessel is pristine. Highly recommend him. I recommend booking at least 2-3 days because one is never enough!
Harrison LloydGoogle review · Dec 2025 - ★★★★★
Jesse is a great guy- my husband has been fishing with him for years and always enjoys the experience. Jesse is great at bringing you to where the fish are and is just enjoyable to be around. Would definitely recommend booking a charter with Flyin High Charters!
Kira KriegerGoogle review · Dec 2025 - ★★★★★
If you’re in the Florida Keys and want an incredible charter experience, book with Captain Jesse! Super knowledgeable and stress free experience. Can’t wait to book again
Ry TheFlyGoogle review · Dec 2025 - ★★★★★
Jess was a wonderful and knowledgeable captain. We enjoyed our charter with Flyin High Charters. I highly recommend them to anyone wanting to fish off the Florida Keys. Thank you Jess for a memorable experience.
Jamie RobbinsGoogle review · Dec 2025 - ★★★★★
Have had many great days with Captain Jesse he is great and puts you on the fish. Super great experience fishing with him definitely can’t wait to fish again!!
Colton RegiGoogle review · Dec 2025 - ★★★★★
Jesse is awesome and I have great pics/videos of the memories to prove it!! Looking forward to fishing with you again this spring!!
Alvin BellGoogle review · Dec 2025 - ★★★★★
Highly recommend Capt Jesse! Go fish with him you won’t regret it!
Andy BowenGoogle review · Dec 2025
Book a trip
Pick your dates. Jess plans the rest.
Send your dates and a few details. Jess will call or text to talk through the tides, the target species, and where to meet. Spring tarpon dates fill first.
- $200 deposit holds your date
- Weather calls rescheduled or refunded
- First-timers and kids welcome