Damn Good Sheepshead Fishing Charters In The Florida Keys

Check real-time availability and compare rates on Florida Keys sheepshead fishing trips. Confidently book your next day on the water.

Choose a Date
4.98/5 Average Rating

Damn Good Guides

Experts Available 24/7

100% Weather Guarantee

Recently Booked Sheepshead Fishing Charters In The Florida Keys

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 Islamorada

Epic Islamorada Inshore

100% (34)
25 ft 1 - 4 People From $650
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Key Largo

Key Largo Adventure

100% (77)
24 ft 1 - 6 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Islamorada

Islamorada Fishing Experience

100% (3)
25 ft 1 - 4 People From $675
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 Islamorada

Everglades Inshore Trip

100% (28)
24 ft 1 - 6 People From $650

“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

Other Captain Experiences Trips in the Florida Keys

Bucket List
The Captain Experiences team chose this trip as one for the bucket list.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Tavernier

Tavernier Backcountry Fishing

100% (24)
18 ft 1 - 3 People From $450
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Key West

Shark Fishing Key West

100% (1)
34 ft 1 - 2 People From $900
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 Fishing in Key West

Key West Fishing Adventure

100% (46)
24 ft 1 - 8 People From $800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea Fishing in Key West

Laid Back Key West

100% (12)
33 ft 1 - 6 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Key Largo

Key Largo Silver Kings

100% (77)
24 ft 1 - 6 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Everglades City

Everglades Action

NEW
23 ft 1 - 4 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Key Largo

Key Largo Bays And Backcountry

100% (18)
25 ft 1 - 8 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Key Largo

Key Largo Backcountry

100% (77)
24 ft 1 - 6 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Key West

Beautiful Backcountry Fishing

100% (2)
24 ft 1 - 4 People From $800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key Largo

Key Largo Offshore Fishing

100% (17)
35 ft 1 - 6 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key Largo

Key Largo Offshore Fishing Trip

100% (77)
24 ft 1 - 6 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Key West

Targeting Tarpon In Key West

100% (13)
24 ft 1 - 4 People From $800

Need a Place to Stay?

Want to Stay Put?

Everything to Know About Booking a Florida Keys sheepshead fishing charter

Why should I book a sheepshead fishing charter in the Florida Keys with Captain Experiences?

Our Damn Good Guides currently offer 4 sheepshead trips in the Florida Keys, and the most popular trips in the area are Epic Islamorada Inshore guided by Ron, Islamorada Fishing Experience guided by Alex, and Key Largo Adventure guided by Andrew.

Our guides in the Florida Keys are rated a 4.98 out of 5 based on 5098 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 sheepshead guides / fishing lessons in the Florida Keys? Check out our beginner and family friendly sheepshead guides in the Florida Keys.

What types of sheepshead fishing charters are common in the Florida Keys?

Deep Sea fishing is the most popular type of fishing for sheepshead in the Florida Keys as well as inshore fishing, nearshore fishing, and flats fishing.

The most common fishing techniques in the Florida Keys are light tackle fishing, live bait fishing, and bottom fishing but artificial lure fishing and heavy tackle fishing are popular as well.

How much do Florida Keys sheepshead fishing charters cost?

Prices for sheepshead in the Florida Keys can range anywhere from about $700 to $1,138, but the average price for a half day trip for sheepshead in the Florida Keys is $760. The average price for a full day trip for sheepshead in the Florida Keys is $1,012.

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 sheepshead fishing in the Florida Keys?

The most popular season for sheepshead fishing in the Florida Keys is summer, and most anglers book their trips 20 days in advance.

Do I need a the Florida Keys fishing license for sheepshead and what are the bag limits for sheepshead in the Florida Keys?

See here for more information on sheepshead fishing licenses in the Florida Keys, sheepshead bag limits, and fishing season regulations for sheepshead in the Florida Keys. When in doubt, your fishing guide will always know the right sheepshead rules and regulations in the Florida Keys.

Recent Reviews

  • ★★★★★
    He was a great captain. We had an awesome time. Would absolutely recommend him to everyone. If we make it down again we would book with him again.

    Melanie R. | June 16, 2025

    Trip: Everglades Inshore Trip

  • ★★★★★
    We had a great time. Mark went above and beyond to put us on fish (which he did). lots of fish and lots of laughs. more importantly than Mark being the best guide I ever had, hes a great person. Top notch human being. He gets just as excited when you hook up as you do. Geat sportsman and you can tell he truly loves what he does.

    Bill W. | June 14, 2025

    Trip: Everglades Inshore Trip

  • ★★★★★
    Capt. Mark did an awesome job finding the fish today! He was willing to go wherever it was needed to find Tarpon, which we definitely able to do. Even when the wind came up, he worked to make the ride back comfortable. My grandson and I both appreciated all of Capt. Marks expertise and hard work to make for an excellent fishing trip!

    Louis F. | May 26, 2025

    Trip: Everglades Inshore Trip

  • ★★★★★
    Believe all the good reviews Andrew has. We had such a great time in the Everglades catching sea trout, jacks, snapper, snook, a bull shark and a nurse shark. Couldn’t have been more pleased with this captain and deckhand. Very polite and prompt on getting you baited up and back in the water. If you are reading this review and wondering who to book a trip with, do not hesitate to book with Andrew.

    Kevin W. | May 6, 2025

    Trip: Key Largo Adventure

  • ★★★★★
    Had a great time with Mark! Had a lot of fun and he put us on fish. Caught Cobia, Jack Crevalle, a bunch of trout and a 150 lb Shark!! Hooked up 3 Tarpon!! He is your guy if you want to have fun and catch fish.

    Dave S. | May 5, 2025

    Trip: Everglades Inshore Trip

Featured Cities

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 Sheepshead Trips in the Florida Keys