Damn Good Fly Fishing Charters In Stock Island

Check real-time availability and compare rates on Stock Island fly fishing fishing trips. Confidently book your next day on the water.

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Recently Booked Fly Fishing Charters In Stock Island, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Stock Island

Key West Offshore Experience

100% (4) Guided by Chris
42 ft 1 - 6 People From $1,200
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Cudjoe Key

Lower Keys Flats Fishing

100% (2) Guided by Dale
17 ft 1 - 2 People From $600
Bucket List
The Captain Experiences team chose this trip as one for the bucket list.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Dry Tortugas Fishing Trip

100% (11) Guided by Rob
36 ft 1 - 6 People From $2,800
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Summerland Key

Summerland Key Flats Action

100% (19) Guided by Brandon
17 ft 1 - 3 People From $400
Damn Good
Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Big Pine Key

Florida Keys Destination Fishing

100% (4) Managed by Alex
28 ft 1 - 8 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Key West

Key West On Light Tackle & Flies

100% (11) Guided by Jamie
17 ft 1 - 2 People From $600
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Top Types of Fly Fishing Trips in Stock Island

Top Species for Fly Fishing in Stock Island

“Our Damn Good Guides go above and beyond, and we’ve handpicked every single one. We’re passionate about the outdoors and look forward to getting you out on the trip of a lifetime, every time.”

Jonathan and Attison   |   Co-founders   |   Austin, Texas

All Target Species in Stock Island

View Full Species Seasonality Chart »
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

More Fly Fishing Charters In Stock Island, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Summerland Key

Florida Keys Bonefish & Permit

100% (6) Guided by Bob
18 ft 1 - 2 People From $500
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Full Day Private Fishing Charter

94% (17) Guided by John
25 ft 1 - 4 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Summerland Key

Summerland Key Tarpon Fishing

100% (6) Guided by Bob
18 ft 1 - 2 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Key West

Keys Flats & Backcountry Fishing

100% (1) Guided by Karl
16 ft 1 - 2 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Morning 1/2 Day Fishing Charter

94% (17) Guided by John
25 ft 1 - 4 People From $800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Key West

Second Generation Bay Boat

100% (11) Guided by Rob
25 ft 1 - 8 People From $700
See All Fly Fishing Trips in Stock Island

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Everything to Know About Booking a Stock Island fly fishing charter

Why should I book a fly fishing charter in Stock Island with Captain Experiences?

Our Damn Good Guides currently offer 19 fly fishing trips in Stock Island, and the most popular trips in the area are Key West Offshore Experience guided by Chris, Lower Keys Flats Fishing guided by Dale, and Dry Tortugas Fishing Trip guided by Rob.

Our guides in Stock Island are rated a 4.92 out of 5 based on 5945 verified reviews on Captain Experiences.

All guides on Captain Experiences are vetted by our team. You can access their reviews, click through trip photos, read bios to get to know them, and preview trip details like species, techniques, group sizes, boat specs and more.

Looking for kid friendly fly fishing guides / fishing lessons in Stock Island? Check out our beginner and family friendly fly fishing guides in Stock Island.

What types of fly fishing charters are common in Stock Island?

Deep Sea fishing is the most popular type of fishing for fly fishing in Stock Island as well as inshore fishing, flats fishing, and deep sea fishing.

The most commonly sought after species for fly fishing in Stock Island are: 1. bonefish, 2. permit, 3. tarpon, 4. gag grouper, and 5. goliath grouper.

How much do Stock Island fly fishing charters cost?

Prices for fly fishing in Stock Island can range anywhere from about $550 to $2,400, but the average price for a half day trip for fly fishing in Stock Island is $913. The average price for a full day trip for fly fishing in Stock Island is $1,409.

Is booking a fishing guide worth the money?

Hiring a guide provides a number of benefits and many choose to book a fishing guide for a combination of experience, local knowledge, convenience, and cost-effectiveness.

Working with experienced fishing guides who know the best local spots and techniques can dramatically increase your odds of a great day. Having someone who is on the water every day and knows the area like the back of their hand is going to give you the best chances of success.

Booking a guide is also more cost effective, especially if you only get out a handful of times per year. When you consider all of the costs you would incur on your own such as the price of a boat, maintenance, insurance, gas, high-quality gear and tackle, repairs, and more, you’ll find that DIY is sometimes not worth the expense.

Even if you’ve got a great setup already in your home waters, booking a guide also provides a great opportunity to experience new techniques, new locations, or even a chance at a new target species to knock off the bucket list.

What month is best for on a fly fishing charter in Stock Island?

The most popular season to go on a fly fishing charter in Stock Island is spring, and most anglers book their trips 20 days in advance.

Do I need a Stock Island fishing license and what are the bag limits in Stock Island?

See here for more information on fishing licenses in Stock Island, bag limits for target species, and fishing season regulations in Stock Island. When in doubt, your fishing guide will always know the right rules and regulations in Stock Island.

Recent Reviews

  • ★★★★★
    Captain Jamie took us out in the early afternoon, and even though we knew the bite was a little slow at this time, we just wanted to get out and enjoy the water around beautiful Key West. He made the most of our four hours; we hit around four spots and even cruised over to the ocean side to try and find the bite that way. In this 4-hour trip, I got a crash course in fly fishing from one of the best. Jamie’s super laid-back, easy to talk to, and knows the area like the back of his hand. We wrapped up the trip with a gorgeous sunset; it was a 10/10 day all around. Even with the slow bite, it was one of the most scenic, educational, and unforgettable trips I’ve ever been on!

    Jonathan N. | November 6, 2025

    Trip: Key West On Light Tackle & Flies

  • ★★★★★
    Sean is the man!! We hopped out for an afternoon half day right on the tail end of some weird weather patterns and didn't have high hopes, but Sean relentlessly tried new techniques and locations to get us on some fish. I don't know that I've ever been out with a guide who has moved more or tried more techniques in a 4 hour fishing trip. He knew exactly when to say "this isn't working the fish aren't here, lets move on" which is an underrated skill in a guide. We found the flats empty of the usual suspects (tarpon permit bonefish), but we pivoted and hooked into cero mackerel, mutton snapper, and some barracuda. Sean has been fishing in Key West for 30+ years and won't steer you wrong!

    Jonathan N. | November 5, 2025

    Trip: Keys Flats And Back Country Trip

  • ★★★★★
    The best

    Jodie R. | October 9, 2025

    Trip: Dry Tortugas Fishing Trip

  • ★★★★★
    We had an absolutely unforgettable day on the water with Captain Mason! Our family of six—ranging from more "seasoned" to children—was treated to a private fishing excursion that truly exceeded all expectations. From the moment we stepped on the boat, the Mason made us feel completely at ease. He was incredibly accommodating, making sure each of us was comfortable, engaged, and having a great time. Whether it was adjusting for the kids' needs, helping with baiting hooks, or offering fishing tips to the beginners among us, his patience and positive energy never wavered. What stood out the most was how safe and inclusive he made the entire experience. Every member of the family felt like part of the crew. He kept a watchful eye on everything while still creating a laid-back, fun atmosphere. We never once felt rushed or out of place—just fully present and enjoying every moment. He also went above and beyond in every possible way—from extending our time a bit when the fish were biting to showing us local wildlife and secret spots only a seasoned pro would know. It truly felt like a one-of-a-kind adventure curated just for us. Highly recommend this charter to anyone looking for a fun, family-friendly, and expertly guided day on the water. Can’t wait to book again next time we’re in town!

    Lee D. | July 10, 2025

    Trip: Dry Tortugas Fishing Trip

  • ★★★★★
    Rainy,captain put his best foot forward..,.,appreciate the effort but still disappointed..so be it

    John R. | June 24, 2025

    Trip: Lower Keys Flats Fishing

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Didn't Find What You Were Looking For?

Our guides are Damn Good Guides, which means they’re vetted by our team of outdoor experts who know them on a first-name basis. We hand pick each and every one of them, and our network spans all across the US and beyond.

The proof is in the pudding, and we’re incredibly proud of our 4.9 / 5 average review score. Hit the button below to see more trip options:

See All Fly Fishing Trips in Stock Island