Damn Good Sheepshead Fishing Charters In Captiva Island

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

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Recently Booked Sheepshead Fishing Charters In Captiva Island

Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Cape Coral

8 Hours Inshore

100% (6)
26 ft 1 - 8 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Dolphin Watching, Shelling in Captiva

Captiva And Sanibel Fishing Trip

100% (2)
24 ft 1 - 12 People From $350
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 Cape Coral

6 Hour Inshore

100% (6)
26 ft 1 - 4 People From $800
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 Fort Myers Beach

Fort Myers/Sanibel Fishing Trip

100% (54)
24 ft 1 - 5 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Fort Myers Beach

Fort Myers Fishing Trip

NEW
26 ft 1 - 6 People From $600
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Cape Coral

4 Hour Inshore

100% (6)
26 ft 1 - 8 People From $600

Top Types of Sheepshead Trips in Captiva 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

More Sheepshead Fishing Charters In Captiva Island

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

Inshore, Nearshore, Flats in Cape Coral

4 Hour Inshore

100% (6)
26 ft 1 - 8 People From $600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Fort Myers Beach

Fort Myers Fishing Trip

NEW
26 ft 1 - 6 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 Fort Myers Beach

Fort Myers/Sanibel Fishing Trip

100% (54)
24 ft 1 - 5 People From $550
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 Cape Coral

6 Hour Inshore

100% (6)
26 ft 1 - 4 People From $800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Dolphin Watching, Shelling in Captiva

Captiva And Sanibel Fishing Trip

100% (2)
24 ft 1 - 12 People From $350
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Cape Coral

8 Hours Inshore

100% (6)
26 ft 1 - 8 People From $1,000
See All Sheepshead Trips in Captiva Island

Other Captain Experiences Trips in Captiva Island

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Fort Myers

Fort Myers / Sanibel Inshore Action

100% (5)
18 ft 1 - 2 People From $425
Fishing in Destin
Fishing in Destin
Fishing in Destin

Jetty Fishing in Bradenton

Boca Grande Tarpon Trip

100% (30)
25 ft 1 - 3 People From $800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Captiva

SWFL Inshore Trip

NEW
40 ft 1 - 4 People From $600
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Cape Coral

Inshore Fishing Charter Cape Coral

99% (130)
26 ft 1 - 12 People From $475
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Captiva

SWFL Inshore/Nearshore Trip

NEW
23 ft 1 - 5 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Saint James City

Inshore Back Water Fishing Trip

NEW
18 ft 1 - 3 People From $500

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Everything to Know About Booking a Captiva Island sheepshead fishing charter

Why should I book a sheepshead fishing charter in Captiva Island with Captain Experiences?

Our Damn Good Guides currently offer 6 sheepshead trips in Captiva Island, and the most popular trips in the area are 8 Hours Inshore guided by Al, Captiva And Sanibel Fishing Trip guided by Ray, and 6 Hour Inshore guided by Al.

Our guides in Captiva Island are rated a 4.96 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 sheepshead guides / fishing lessons in Captiva Island? Check out our beginner and family friendly sheepshead guides in Captiva Island.

What types of sheepshead fishing charters are common in Captiva Island?

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

The most common fishing techniques in Captiva Island are light tackle fishing, bottom fishing, and cut bait fishing but jigging and live bait fishing are popular as well.

How much do Captiva Island sheepshead fishing charters cost?

Prices for sheepshead in Captiva Island can range anywhere from about $600 to $1,400, but the average price for a half day trip for sheepshead in Captiva Island is $902. The average price for a full day trip for sheepshead in Captiva Island is $1,245.

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 Captiva Island?

The most popular season for sheepshead fishing in Captiva Island is spring, and most anglers book their trips 25 days in advance.

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

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

Recent Reviews

  • ★★★★★
    Captain is a real professional!! We were on snook minutes from leaving the dock. We caught Red grouper, gag grouper, mangrove snapper and snook. My wife and I highly recommend Captain James.

    Jack L. | November 15, 2025

    Trip: Fort Myers/Sanibel Fishing Trip

  • ★★★★★
    Captain Ray was knowledgable about area and fishing spots. He was a great guy and a well trained captain. However, we paid for 5 people on a charter and only 2 - 3 poles were ever in the water. This was due to high chop but still somewhat disappointing. I would try captain Ray again.

    Marc M. | August 12, 2025

    Trip: Captiva And Sanibel Fishing Trip

  • ★★★★★
    James is the man! He knew right where the fish would be. He was also great with our kids helping them and teaching them the ways, especially with our young daughter who beat us all. Both kids had a blast. Our family had a great time! We will definitely be going out with you againa. Thanks again, James!

    Donald S. | August 11, 2025

    Trip: Fort Myers/Sanibel Fishing Trip

  • ★★★★★
    We had a phenomenal experience with James! He was knowledgeable and funny with a clean boat and excellent fishing equipment. Highly recommend ⭐️⭐️⭐️⭐️⭐️

    Tammy P. | July 19, 2025

    Trip: Fort Myers/Sanibel Fishing Trip

  • ★★★★★
    James was great and put us on the fish right away. Knowledgeable and friendly, our family had a great time.

    Brandon C. | March 21, 2025

    Trip: Fort Myers/Sanibel Fishing Trip

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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 Sheepshead Trips in Captiva Island