Hello world!
October 17, 2025
Flyin’ High Charters offers tailored fly and light tackle trips across the Lower Florida Keys. Whether you’re sight fishing the flats for tarpon, permit, and bonefish or exploring quiet backcountry waters, every trip is built around the tides, the weather, and your goals as an angler.
We offer multiple types of fishing charters to get you out on the water here in the Florida Keys and Key West. Most trips run throughout the Lower Keys — anywhere from Big Pine Key down to Key West.
Our most popular fishing charters are backcountry trips targeting the Big Three: bonefish, permit, and tarpon. Anglers travel from all over the world to experience the thrill of chasing these fish in the Florida Keys. This is a destination fishery for those looking to test their skills and pursue the catch of a lifetime.
These trips are designed for the hardcore angler. Whether you’re a fly fishing junkie or a sight-fishing expert with a spinning rod, Captain Jesse will work with you to target that bucket-list fish you’ve been dreaming about.
We also offer charters geared toward other species and skill levels. New to flats fishing? No problem. We’re here to help you learn techniques that will make you a stronger angler — both on the flats and in your home waters. Anglers can target less technical species like barracuda and big sharks. There’s nothing quite like throwing big lures to angry barracuda or chumming a flat for aggressive, frenzied sharks.
If you’re not that into fishing but love being on the water, we’ve still got you covered. We offer snorkeling trips and sunset cruises for those who want to experience the natural beauty of the Lower Keys without picking up a rod.
Every charter is built around the tides, weather, and what you want out of the day. We can spend hours sight-fishing the flats for technical shots, or mix in more action-oriented opportunities in the backcountry. Trips typically start early to take advantage of the light and tide windows that make this fishery so special.
Whether you’re a seasoned angler or brand new to saltwater fly fishing, I’ll walk you through everything you need to know — from spotting fish to reading tides to making confident shots in real-world conditions.
The Lower Keys offer two very different experiences, and a big part of the fun is matching the trip to your personality as an angler.
If you’re unsure which route is best, I’ll help you choose based on conditions and what you’re hoping to get out of the trip.
While many of our trips are geared toward serious anglers, we also love working with beginners and families. The backcountry is especially well suited for:
You don’t need experience — just a willingness to learn and have fun.
All charters include premium fly and light-tackle gear built for the Keys:
If you want to bring your own setup, I’m happy to rig it and help you dial it in for the day.
Peak seasons fill quickly — especially tarpon season (April–June) and fall permit season (July–October).
Aim to book:
Most charters launch from Big Pine Key, but depending on the tide and weather, we may fish anywhere throughout:
Booking is simple — tell me the kind of experience you’re looking for, and I’ll handle the rest.
Call/Text: (407) 448-2017
Email: Capt.JesseRegister@live.com
(407) 448-2017
Let’s get your trip on the books. Send over a few details and I’ll reach out personally to lock in your dates.