Damn Good Fly Fishing Charters In Big Pine Key

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

Choose a Date
4.91/5 Average Rating

Recently Booked Fly Fishing Charters In Big Pine Key, Fl

Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Big Pine Key

Florida Keys Destination Fishing

100% (4)
28 ft 1 - 8 People From $1,000
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Big Pine Key

Summerland Key Flats Fishing

100% (6)
17 ft 1 - 2 People From $600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Big Pine Key

Big Pine Key Fly Or Light Tackle

100% (1)
18 ft 1 - 2 People From $750
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)
17 ft 1 - 3 People From $400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Summerland Key

Florida Keys Bonefish & Permit

100% (9)
18 ft 1 - 2 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Summerland Key

Summerland Key Tarpon Fishing

100% (9)
18 ft 1 - 2 People From $500

Top Types of Fly Fishing Trips in Big Pine Key

What makes Captain Experiences Damn Good?

Damn Good Guides

You will only find quality, vetted guides on Captain Experiences, and we know them all on a first-name basis.

Damn Good Guides

Experts Available 24/7

Our US-based team is available 24/7 to help you with any questions or concerns.

Experts Available 24/7

100% Weather Guarantee

We want to keep everyone safe, so if the weather is bad we'll work with you to reschedule at no cost.

100% Weather Guarantee

4.9 / 5 Average Rating

We hand pick our Damn Good Guides, and our network spans across North America and beyond.

4.9 / 5 Average Rating

“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

Top Species for Fly Fishing in Big Pine Key

All Target Species in Big Pine Key

  • 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 Big Pine Key, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Cudjoe Key

Big Pine Key Action

100% (5)
18 ft 1 - 2 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Cudjoe Key

Lower Keys Flats Fishing

100% (3)
17 ft 1 - 2 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Cudjoe Key

Nighttime Tarpon Adventure

100% (5)
18 ft 1 - 2 People From $600
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

Inshore, Nearshore, Flats in Marathon

Everglades

100% (25)
24 ft 1 - 4 People From $1,600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Key West

Second Generation Bay Boat

100% (15)
24 ft 1 - 8 People From $700
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

Inshore, Flats Fishing in Key West

Keys Flats And Back Country Trip

100% (10)
18 ft 1 - 2 People From $500

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:

Everything to Know About Booking a Big Pine Key fly fishing charter

What are the best fly fishing charters in Big Pine Key?

The best fly fishing charters in Big Pine Key are:

Why should I book a fly fishing charter in Big Pine Key with Captain Experiences?

Our Damn Good Guides currently offer 22 fly fishing trips in Big Pine Key, and the most popular trips in the area are Florida Keys Destination Fishing guided by Alex, Summerland Key Flats Fishing guided by Ben, and Big Pine Key Fly Or Light Tackle guided by Zach.

Our guides in Big Pine Key are rated a 4.91 out of 5 based on 8350 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 Big Pine Key? Check out our beginner and family friendly fly fishing guides in Big Pine Key.

What types of fly fishing charters are common in Big Pine Key?

Deep Sea fishing is the most popular type of fishing for fly fishing in Big Pine Key as well as inshore fishing, flats fishing, and nearshore fishing.

The most commonly sought after species for fly fishing in Big Pine Key are: 1. bonefish, 2. jack crevalle, 3. permit, 4. redfish, and 5. snook.

How much do Big Pine Key fly fishing charters cost?

Prices for fly fishing in Big Pine Key can range anywhere from about $600 to $2,000, but the average price for a half day trip for fly fishing in Big Pine Key is $825. The average price for a full day trip for fly fishing in Big Pine Key is $1,291.

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 Big Pine Key?

The most popular season to go on a fly fishing charter in Big Pine Key is spring, and most anglers book their trips 17 days in advance.

Do I need a Big Pine Key fishing license and what are the bag limits in Big Pine Key?

See here for more information on fishing licenses in Big Pine Key, bag limits for target species, and fishing season regulations in Big Pine Key. When in doubt, your guide will always know all the relevant rules and regulations in Big Pine Key.

Recent Reviews

  • ★★★★★
    Great birthday trip!

    Kate H. | July 14, 2026

    Trip: Key West Light Tackle Fishing

  • ★★★★★
    Jamie was fantastic and very knowledgeable. He knew of all the places where the tarpon bonefish and barracudas would be. My wife and I had an amazing time and would definitely book with him again. Thanks for a great day!

    Bryan K. | July 13, 2026

    Trip: Key West On Light Tackle & Flies

  • ★★★★★
    Bob is the real deal. He put me on the fish right away. Super patient and knowledgeable of the area. Strongly recommend a trip with Bob!

    Milton T. | June 28, 2026

    Trip: Summerland Key Tarpon Fishing

  • ★★★★★
    He Knows where fish are and will get you opportunities to catch em. Very knowledgeable about his craft and puts in the time to get you shots at your target species!

    Michael S. | June 17, 2026

    Trip: Summerland Key Tarpon Fishing

  • ★★★★★
    As an avid fisherman, I can say that Capt. K is a very respectable fishing guide. He has put the time in and knows the local waters very well and which fish to target. We hooked into my first tarpon and got a photo of a lifetime while on my trip. Great guy and very likable. Highly recommend a trip with him.

    Caleb M. | May 23, 2026

    Trip: Key West Light Tackle Fishing

Narrow Down Your Search

Last updated: July 17, 2026

Enter to Win a

$500 DAMN GOOD GIFT CARD

Gift Card

Sign up to win $500 towards ANY trip. Winners drawn monthly.

By subscribing, you agree to receive marketing communications from Captain Experiences. To opt-out, click the unsubscribe button at the bottom of our emails. Privacy Policy and Terms & Conditions

See All Fly Fishing Trips in Big Pine Key