Damn Good Sheepshead Fishing Charters In The Pine Island Sound

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

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Recently Booked Sheepshead Fishing Charters In The Pine Island Sound

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Fort Myers Beach

4 Hr Fishing Fun

100% (1)
23 ft 1 - 8 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 Bokeelia

4-8 Hours Inshore Trip

NEW
22 ft 1 - 6 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Matlacha

4 - 8 Hour Trips With Capt. Logan

100% (7)
22 ft 1 - 8 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats, Eco Tour in Saint James City

Half Day (AM)

100% (1)
22 ft 1 - 8 People From $550
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, Nearshore Fishing in Fort Myers Beach

Fort Myers Inshore Fishing Trip

100% (9)
25 ft 1 - 6 People From $525

Top Types of Sheepshead Trips in the Pine Island Sound

“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 The Pine Island Sound

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

Inshore, River, Flats in Fort Myers

Fishing Thrills In Fort Myers

100% (5)
22 ft 1 - 4 People From $550
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 Fishing in Matlacha

Inshore Charter

100% (5)
20 ft 1 - 8 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Cape Coral

Inshore/Flats Trip

NEW
26 ft 1 - 6 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, River, Flats in Cape Coral

Inshore Bay / Flats

100% (14)
25 ft 1 - 6 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats, Eco Tour in Saint James City

Half Day (PM)

100% (1)
22 ft 1 - 4 People From $550
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Bokeelia

Cape Coral Inshore Excursion

100% (9)
22 ft 1 - 6 People From $550
See All Sheepshead Trips in the Pine Island Sound

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Everything to Know About Booking a Pine Island Sound sheepshead fishing charter

Why should I book a sheepshead fishing charter in the Pine Island Sound with Captain Experiences?

Our Damn Good Guides currently offer 13 sheepshead trips in the Pine Island Sound, and the most popular trips in the area are 4 Hr Fishing Fun guided by Brian, 4-8 Hours Inshore Trip guided by Andy, and 4 - 8 Hour Trips With Capt. Logan guided by Logan.

Our guides in the Pine Island Sound are rated a 4.97 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 the Pine Island Sound? Check out our beginner and family friendly sheepshead guides in the Pine Island Sound.

What types of sheepshead fishing charters are common in the Pine Island Sound?

Inshore fishing is the most popular type of fishing for sheepshead in the Pine Island Sound as well as nearshore fishing, flats fishing, and river fishing.

The most common fishing techniques in the Pine Island Sound are artificial lure fishing, cut bait fishing, and light tackle fishing but live bait fishing and sight casting are popular as well.

How much do Pine Island Sound sheepshead fishing charters cost?

Prices for sheepshead in the Pine Island Sound can range anywhere from about $550 to $1,500, but the average price for a half day trip for sheepshead in the Pine Island Sound is $865. The average price for a full day trip for sheepshead in the Pine Island Sound is $1,146.

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 Pine Island Sound?

The most popular season for sheepshead fishing in the Pine Island Sound is spring, and most anglers book their trips 18 days in advance.

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

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

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

  • ★★★★★
    Excellent day on the water with Logan and Austin. We will enjoy another day on the water with Logan and Austin in the spring. Both knowledgeable fishermen and great people.

    Earl S. | November 1, 2025

    Trip: 4 - 8 Hour Trips With Capt. Logan

  • ★★★★★
    Had a great time catching fish. Billy was patient with us and extremely helpful. 10 out of 10 would recommend!

    Sebastian L. | October 4, 2025

    Trip: Inshore Bay / Flats

  • ★★★★★
    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

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See All Sheepshead Trips in the Pine Island Sound