Pricing & Availability

To review Pricing and Availability, please select your Trip Date, Duration, Group Size, and Start Time.

Please fill out Trip Date, Duration, Group Size, and Start Time above before proceeding.

Fishing Info


Fly Fishing

Water Type

Inshore, Flats

Skill Level

Beginner, Intermediate, Advanced


Barracuda, Bonefish, Jack Crevalle, Permit, Snook, Tarpon

About Your Guide

Captain Dexter Simmons looks forward to chasing down the coveted Grand Slam of catching a Tarpon, Bonefish, and Permit in the same day with you on your next trip down to Key West Florida.

Captain Dexter of Key West Fly Fishing offers trips across the Florida Keys, Key West, Marquesas, Bahamas, the Caribbean, Belize, and Cuba and his happy to fish with fly or spinning tackle.

While one might assume these are expert-only trips, that couldn't be further from the truth. Captain Dexter loves hosting families as well, and will adjust his trips to cater to the needs of every group individually.

Check out his availability below to get in on the fantastic, world-class fishing these amazing destinations provide while fishing with Captain Dexter Simmons of Key West Fly Fishing!


Robert R.

October 16, 2018

Went fishing with Captain Dexter with my son last week. It was Christmas present trip and his bucket list to catch a bonefish. Capt. Dexter did everything he could to find the silver bullets of the flats with us landing five of the hardest fighting fish regardless of their size. Highly recommend Captain to anyone who wants to catch fish or a specific kind of fish.

Kelton K.

July 5, 2016

Capt. Dexter is a fantastic guide! Put me on tarpon had several hook ups, including an hour long battle. Very patient and clear with directions. Highly recommend.



All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.


Feel free to enjoy responsibly, but please no glass.


You will get a refund if the trip is canceled due to weather.

Boat Restroom

No, this boat does not have a bathroom on board.


No meal provided.

Gear & Packing


Rods, reels, tackle

At an Additional Rate

No added costs.

Recommended Packing

Polarized sunglasses (amber color is best), light weather gear (jacket), billed cap, whatever you want for lunch, sunscreen.

Required Items

A valid fishing license.

Things to Keep in Mind

Payment & Tipping

After paying the deposit, a QR Code will be emailed to you. On the day of the trip, your guide will scan your QR code to automatically transfer the remaining balance. The only cash needed is for a 10-20% customary tip.

Cancellation/Refund Policy

Yes, cancel for free up to 60 days before the trip.

Where to Buy a Fishing License

Find a license for your state here.


Start Location

Key West, Florida, USA

Start Time(s)

07:00 AM, 08:00 AM, 01:00 PM, 02:00 PM


4 hours, 6 hours, 8 hours,