Damn Good Sheepshead Fishing Charters In Estero Bay

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

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Recently Booked Sheepshead Fishing Charters In Estero Bay

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Fort Myers Beach

Fort Myers Hook Up!

100% (1)
23 ft 1 - 12 People From $600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Cape Coral

Inshore Bay Trip - 23' Aqua Star

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

Inshore, Flats Fishing in Matlacha

Cape Coral Inshore - 21’ Tidewater

NEW
21 ft 1 - 4 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Fort Myers

Fishing Thrills In Fort Myers

NEW
22 ft 1 - 4 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Naples

4 Hour Backwater/Nearcoastal

NEW
23 ft 1 - 4 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Fort Myers Beach

Fort Myers Inshore Fishing Trip

100% (3)
25 ft 1 - 6 People From $525

Top Types of Sheepshead Trips in Estero Bay

“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

More Sheepshead Fishing Charters In Estero Bay

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Fort Myers Beach

Fort Myers Inshore Fishing Trip

100% (3)
25 ft 1 - 6 People From $525
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Naples

4 Hour Backwater/Nearcoastal

NEW
23 ft 1 - 4 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Fort Myers

Fishing Thrills In Fort Myers

NEW
22 ft 1 - 4 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Matlacha

Cape Coral Inshore - 21’ Tidewater

NEW
21 ft 1 - 4 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Cape Coral

Inshore Bay Trip - 23' Aqua Star

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

Inshore, Nearshore Fishing in Fort Myers Beach

Fort Myers Hook Up!

100% (1)
23 ft 1 - 12 People From $600
See All Sheepshead Trips in Estero Bay

Other Trips in Estero Bay

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Fort Myers Beach

Fishing Trip 5 Miles Out

100% (1)
30 ft 1 - 6 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Fort Myers Beach

Inshore Fishing Charter

NEW
22 ft 1 - 6 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Pine Island Center

Inshore Fishing At Its Finest!!!

NEW
17 ft 1 - 2 People From $400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Naples

4 Hour Inshore/Nearshore

67% (3)
23 ft 1 - 4 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Fort Myers Beach

Fishing Trip 25 Miles Out (State Waters)

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

Inshore Fishing in Fort Myers Beach

Fishing Trip Bay Fishing

100% (1)
30 ft 1 - 6 People From $500

Need a Place to Stay?

Everything to Know About Booking an Estero Bay sheepshead fishing charter

What are the best sheepshead fishing charters in Estero Bay?

Why should I book a sheepshead fishing charter in Estero Bay with Captain Experiences?

Our Damn Good Guides currently offer 8 sheepshead trips in Estero Bay, and the most popular trips in the area are Fort Myers Hook Up! guided by Jesse, Inshore / Backwater Fishing guided by Geoff, and Cape Coral Inshore - 21’ Tidewater guided by Drew.

Our guides in Estero Bay are rated a 5 out of 5 based on 3797 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 Estero Bay? Check out our beginner and family friendly sheepshead guides in Estero Bay.

What types of sheepshead fishing charters are common in Estero Bay?

Inshore fishing is the most popular type of fishing for sheepshead in Estero Bay as well as flats fishing, nearshore fishing, and river fishing.

The most common fishing techniques in Estero Bay are live bait fishing, light tackle fishing, and artificial lure fishing but sight casting and bottom fishing are popular as well.

How much do Estero Bay sheepshead fishing charters cost?

Prices for sheepshead in Estero Bay can range anywhere from about $550 to $1,950, but the average price for a half day trip for sheepshead in Estero Bay is $783. The average price for a full day trip for sheepshead in Estero Bay is $1,284.

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 Estero Bay?

The most popular season for sheepshead fishing in Estero Bay is spring, and most anglers book their trips 9 days in advance.

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

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

Recent Reviews

  • ★★★★★
    Captain Jesse was AMAZING! We had so much fun and were catching fish constantly. A spectacular day on the water with the fabulous Captain Jesse at the helm! So many beautiful birds, wildlife and dolphins!!

    Mary R. | December 7, 2024

    Trip: Fort Myers Hook Up!

  • ★★★★★
    Rod was drip!

    Quinton S. | March 20, 2024

    Trip: Fort Myers Inshore Fishing Trip

  • ★★★★★
    Awesome trip went out with Captain Kenny did a great job put us on fish right away. My wife went along on the trip and she is not a fisher person Kenny did a great job with her and she caught her first shark. Thanks for the great time and unforgettable memories.

    Christopher J. | April 8, 2023

    Trip: Fort Myers Inshore Fishing Trip

  • ★★★★★
    Very good half-day charter. We caught lots of fish right in the bay and would be a great trip for families with kids.

    Bill S. | September 19, 2022

    Trip: Fort Myers Inshore Fishing Trip

  • ★★★★★
    We had a great time and caught a lot of fish we will use Jon again

    Joe W. | December 27, 2021

    Trip: Gallivanting Estero Bay

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 Estero Bay