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.

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Recently Booked Sheepshead Fishing Charters In The Florida Keys

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats Fishing Charter in Islamorada

Epic Islamorada Inshore

100% (8)
25 ft 1 - 4 People From $600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing Charter in Marathon

Marathon Backcountry Flats

NEW
20 ft 1 - 4 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, Nearshore, Flats Fishing Charter in Islamorada

Everglades Inshore Trip

100% (10)
24 ft 1 - 6 People From $650
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats Fishing Charter in Islamorada

Islamorada Fishing Experience

100% (1)
25 ft 1 - 4 People From $675
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing Charter in Key Largo

Key Largo Adventure

100% (25)
24 ft 1 - 6 People From $700

“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 Trips 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, Flats Fishing Charter in Tavernier

Tavernier Backcountry Fishing

100% (8)
18 ft 1 - 3 People From $450
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing Charter in Key West

Shark Fishing Trip

NEW
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 Charter in Key West

Key West Fishing Adventure

100% (7)
24 ft 1 - 8 People From $800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea Fishing Charter in Key West

Laid Back Key West

100% (3)
33 ft 1 - 6 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing Charter in Key Largo

Key Largo Silver Kings

100% (25)
24 ft 1 - 6 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing Charter in Key Largo

Everglades Action

NEW
23 ft 1 - 4 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing Charter in Key Largo

Key Largo Bays And Backcountry

100% (3)
25 ft 1 - 8 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing Charter in Key Largo

Key Largo Backcountry

100% (25)
24 ft 1 - 6 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats Fishing Charter in Key West

Beautiful Backcountry Fishing

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

Deep Sea Fishing Charter in Key Largo

Key Largo Offshore Fishing

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

Inshore, Deep Sea, Nearshore Fishing Charter in Key Largo

Key Largo Reef Trip

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

Nearshore Fishing Charter in Key Largo

Live Baiting And Bottomfishing

NEW
31 ft 1 - 6 People From $900

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Everything to Know About Booking a Florida Keys sheepshead fishing charter

What are the best sheepshead fishing charters in the Florida Keys?

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

Our Damn Good Guides currently offer 5 sheepshead trips in the Florida Keys, and the most popular trips in the area are Epic Islamorada Inshore guided by Ron, Marathon Backcountry Flats guided by Larry, and Islamorada Fishing Experience guided by Alex.

Our guides in the Florida Keys are rated a 4.91 out of 5 based on 3692 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?

Inshore fishing is the most popular type of fishing for sheepshead in the Florida Keys as well as flats fishing and nearshore fishing.

The most common fishing techniques in the Florida Keys are artificial lure fishing, light tackle fishing, and live bait fishing but jigging and cut bait 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 $693 to $1,123, but the average price for a half day trip for sheepshead in the Florida Keys is $745. The average price for a full day trip for sheepshead in the Florida Keys is $1,001.

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 23 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

  • ★★★★★
    Amazing trip! Lots of laughs and tons of fish! We even got our target fish which was tarpon. Captain mark is great and we will definitely use him again.

    Angela F. | September 6, 2024

    Trip: Everglades Inshore Trip

  • ★★★★★
    Captain Andrew, put us on fish right away! He knowledgeable about all things Key Largo. He is professional, organized, and enthusiastic about what he does. We highly recommend captain andrew to anyone, and when we come back we will book with him again. Highlight of the trip was landing the nurse shark!

    Jaime P. | June 5, 2024

    Trip: Key Largo Adventure

  • ★★★★★
    Some times you are fortunate to meet people that leave a deep impression an impregnation on you. Captain Mark is one of these rare persons. I was fortunate to go fishing with him today and we had a blast. He is so kind, so full of knowledge, that I do recommend going fishing with him. His repeated actions around the wounded warrior project are a tribute to his care about his peers and good people in general.

    Cornelissen M. | May 19, 2024

    Trip: Everglades Inshore Trip

  • ★★★★★
    Excellent guide. Worked hard to get us into the fish. Caught over 40 fish. Having snapper and trout for dinner!

    Unknown U. | May 18, 2024

    Trip: Epic Islamorada Inshore

  • ★★★★★
    If you want to be inspired to be a better person, laugh, and catch the most fish out of the Islamorada marina Captain Mark is the way to go. Thanks Mark for a great day. Also thank you for your service to our country and continued surrport of disabled veterans!

    Brian S. | April 6, 2024

    Trip: Everglades Inshore Trip

  • ★★★★★
    We had the best experience with Andrew. He’s a born and raised in Key Largo local and he put us on a bunch of spots where fish were biting. He was so patient when we got tangled or lost our bait and was just in general super friendly and helpful. You can tell he spends his days on the water because there’s no place he’d rather be. And he also cleaned our fish with an amazing alacrity and gave us excellent recommendations on where we could have it cooked for us by highly acclaimed local chefs. It wasn’t just fishing, Andrew was the whole package.

    Erica B. | March 17, 2024

    Trip: Key Largo Adventure

  • ★★★★★
    Captain Ron is a true pro and so nice. My family had a great fishing trip. 10 out of 10🙂

    Mark L. | March 15, 2024

    Trip: Epic Islamorada Inshore

  • ★★★★★
    Captain Ron was awesome! Tons of fun. Caught dozens of fish. He was super helpful. Knew the good spots. Would totally recommend for a great family or couples excursion.

    Cameron S. | February 25, 2024

    Trip: Epic Islamorada Inshore

  • ★★★★★
    What an awesome fishing guide! Omg. We caught so many fish. Cool boat, excellent ability to find the fish, great tips on local ways to get cooked for our dinner. Just had a ball!

    Renotta H. | February 22, 2024

    Trip: Key Largo Adventure

  • ★★★★★
    Ron is the best!!! We had a great morning on the water. We felt so confident in his boating and fishing knowledge. Absolutely headed back again for another day out on his boat. Just a great guy and Master Captain!!!!

    Diane D. | February 2, 2024

    Trip: Epic Islamorada Inshore

  • ★★★★★
    Awesome trip!! Captain Mark is a great guide. Would love to do it again.

    Nancy J. | January 15, 2024

    Trip: Everglades Inshore Trip

  • ★★★★★
    Captain Mark was awesome!!! Highly recommend booking a tour with him.

    Mark N. | January 1, 2024

    Trip: Everglades Inshore Trip

  • ★★★★★
    Captain Andrew was fantastic! Knows his stuff for sure! Caught everything from Jack Crevalle to snook to a 5' bull shark! Will definitely be headed out with him again!

    Tamsin H. | November 5, 2023

    Trip: Key Largo Adventure

  • ★★★★★
    Awesome time. Captain Andrew worked to put us on the fish, we limited out. Great experience.

    Craig N. | October 29, 2023

    Trip: Key Largo Adventure

  • ★★★★★
    Captain Ron was fantastic. He definitely knows where the fish are. He was also cordial and polite. Helped myself and my family the whole time. I highly recommend Captain Ron.

    Christian G. | October 29, 2023

    Trip: Epic Islamorada Inshore

  • ★★★★★
    Amazing

    Irwin M. | October 9, 2023

    Trip: Key Largo Adventure

  • ★★★★★
    Had a great time. Rod is super friendly and knowledgeable. We didn’t slay all the fish but still got some and had fun.

    Patrick O. | September 19, 2023

    Trip: Epic Islamorada Inshore

  • ★★★★★
    Great trip!

    Brian S. | August 12, 2023

    Trip: Epic Islamorada Inshore

  • ★★★★★
    We had a Great time fishing with Captain Mark! He was awesome!

    Derek B. | June 19, 2023

    Trip: Everglades Inshore Trip

  • ★★★★★
    Captain Drew was awesome. We booked a 4 hrs trip and he put us right on fish. He was very personable and knowledgeable. Would definitely book with him again.

    James M. | June 13, 2023

    Trip: Key Largo Adventure

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