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Damn Good Sheepshead Fishing Charters In Holiday

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

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Recently Booked Sheepshead Fishing Charters In Holiday, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter in Holiday

Half Day Trip (4hrs)

100% (2) Guided by Carlos
30 ft 1 - 6 People From $750
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 near Holiday

Tampa Bay Inshore Adventures

100% (11) Guided by Wade
24 ft 1 - 6 People From $400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats Fishing Charter near Holiday

Clearwater Classic

100% (2) Guided by William
21 ft 1 - 4 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, River, Flats Fishing Charter near Holiday

Tampa Bowfishing

100% (2) Guided by Ike
22 ft 1 - 6 People From $575
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing Charter near Holiday

4-6 Inshore Trip

NEW Guided by Dustin
22 ft 1 - 8 People From $450
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing Charter near Holiday

4-8 Hour Fishing Trip

100% (3) Guided by Hank
22 ft 1 - 4 People From $400
View All

Top Types of Sheepshead Trips in Holiday

“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

Target Species in Holiday

View Full Species Seasonality Chart »
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

More Sheepshead Fishing Charters In Holiday, Fl

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, River, Flats Fishing Charter near Holiday

St Petersburg Inshore Fishing!!!

100% (2) Guided by George
24 ft 1 - 5 People From $425
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats Fishing Charter near Holiday

Inshore Fishing Charter

100% (1) Guided by Brian
24 ft 1 - 4 People From $500
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 near Holiday

Tampa Bay Inshore Fun

100% (2) Guided by George
24 ft 1 - 5 People From $400
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 near Holiday

In Or Near Shore Experience

100% (7) Guided by Robert
22 ft 1 - 4 People From $450
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing Charter near Holiday

Sunny Fishing On Tampa Bay

100% (3) Guided by Tyler
23 ft 1 - 2 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing Charter near Holiday

Clearwater Inshore Fishing

100% (3) Guided by Alex
22 ft 1 - 4 People From $500
See All Sheepshead Trips in Holiday

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Everything to Know About Booking a Holiday sheepshead fishing charter

What are the best sheepshead fishing charters in Holiday?

The best sheepshead fishing charters in Holiday are:

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

Our Damn Good Guides currently offer 30 sheepshead trip in Holiday: Half Day Trip (4hrs) guided by Carlos.

Our guides in Holiday are rated a 5 out of 5 based on 3708 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 Holiday? Check out our beginner and family friendly sheepshead guides in Holiday.

What types of sheepshead fishing charters are common in Holiday?

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

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

How much do Holiday sheepshead fishing charters cost?

Prices for sheepshead in Holiday can range anywhere from about $500 to $1,100, but the average price for a half day trip for sheepshead in Holiday is $628. The average price for a full day trip for sheepshead in Holiday is $915.

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 Holiday?

The most popular season for sheepshead fishing in Holiday is spring, and most anglers book their trips 13 days in advance.

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

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

Recent Reviews

  • ★★★★★
    We had a great day with Capt Wade, he was very professional and knowledgeable and shared his experiences with us. We caught Snook, Redfish, and Speckled Trout in numbers and size to satisfy our needs until next time. His lunch recommendation to cook our catch was awesome too.

    Rick R. | November 12, 2024

    Trip: Tampa Bay Inshore Adventures

  • ★★★★★
    It was a great trip. Three of us fished comfortably for a half day. Mother Nature provided the fish, and Nick provided a great atmosphere. Easy to talk to and gave some good local recommendations, will look to book with Nick again in the future.

    Michael L. | September 2, 2024

    Trip: Reel Salty Sportfishing

  • ★★★★★
    Captain Robbie was AWESOME & we had a GREAT time!! Thank y'all!!

    Julie T. | August 11, 2024

    Trip: In or Near Shore Experience

  • ★★★★★
    Nick was a fantastic a knowledgeable guide. His boat was clean and well kept. We are a party of 4 with a 10 and 13 year old. Nick took us to an area where every cast was a catch. Thanks again.

    Jason Q. | August 2, 2024

    Trip: Reel Salty Sportfishing

  • ★★★★★
    Captain Ike is a first class person very polite very nice guy me and my son had a great time will do it again when we come back.

    Chris H. | July 16, 2024

    Trip: Tampa Bowfishing

  • ★★★★★
    We had a great morning on the water with Captain George. He put us over fish right away. First cast went into the cooler! He was very knowledgeable and courteous. We enjoyed our time on his boat!

    Lindy K. | July 9, 2024

    Trip: St Petersburg inshore Fishing!!!

  • ★★★★★
    Captain Wade was incredible. He exposed us to several different species of fish and was very educational. A huge manatee and even sting rays gave us appearances. Definitely worth while. Thank you sir!!!

    Jason V. | June 28, 2024

    Trip: Tampa Bay Inshore Adventures

  • ★★★★★
    We had an amazing time, didn’t get on the fish like we had hoped but still had a blast. That’s why they call it fishing.

    Todd D. | June 22, 2024

    Trip: Reel Salty Sportfishing

  • ★★★★★
    Alex is an awesome guide! Was on time and super fun to hang out with. But mostly importantly he absolutely put me on the fish! Will 100% book Alex again the next time I’m in Clearwater, and you should too if you want the chance to get hooked up with huge tarpon and monster snook!!! A+

    Derek B. | June 19, 2024

    Trip: Clearwater Inshore Fishing

  • ★★★★★
    Great Captain… Last minute trip…. 1st time saltwater fishing for my daughter…..knowledgeable and personable…. Found fish in tough conditions… Will book with him again…. Don’t think I can give a better endorsement than that!

    Joseph S. | June 17, 2024

    Trip: Tampa Bay Inshore Adventures

  • ★★★★★
    My husband and I had an amazing bowfishing trip with Mike. He was extremely nice, helpful, and informative.. and he worked hard to get us on fish. We will definitely book with him again!

    Tara L. | June 17, 2024

    Trip: Bowfishing the Tampa Bay

  • ★★★★★
    Great trip and great captain! Ike is the best!

    Justin C. | June 13, 2024

    Trip: Tampa Bowfishing

  • ★★★★★
    Mike was amazing! Our family had the most fun on this charter and we have done many! He found us a lot to shoot at and we loved seeing all the creatures in the water. My kids said trip of a lifetime.

    Robert A. | June 6, 2024

    Trip: St. Pete Bowfishing

  • ★★★★★
    We had an absolutely amazing time with Captain George! We had several other fishermen passing through that were going on about how it was a “tough day” but not with Captain George!! He put us right on the fish! He was always aware of his surroundings, watching the schools of bait fish, and making sure we were in the most optimal spot. He was very knowledgeable about all of the species we caught throughout the day. We were having such a blast that we added an extra hour to onto our trip, which is when he put us on to the BIGGEST Spanish Mackerel I’ve ever seen!! Just to top it off, he was also very kind and caring. He never lost patience with me when he kept having to cast my pole into difficult spots, and he made sure to remind us to drink plenty of water and reapply sunscreen. At the end of the trip, as he was cleaning our fish, I began to overheat and he knew EXACTLY what to do. He stayed calm, let us stay for a while as I regained my strength, and even checked on me later on in the day. What an amazing experience, captain, and day!! 10/10! We will be fishing with Captain George when we are back this way, and will be referring all of our friends and family!

    Lauren H. | June 6, 2024

    Trip: St Petersburg inshore Fishing!!!

  • ★★★★★
    Great time, great guide. Can’t wait for the next trip.

    Thomas G. | May 28, 2024

    Trip: Reel Salty Sportfishing

  • ★★★★★
    Awesome job! We had a great time! Jim and Joe took care of everything. Amazing trip, would definitely go again!

    Kent W. | May 25, 2024

    Trip: Clearwater Inshore Special

  • ★★★★★
    The four of us had a great time with Captain Nick. The boat was very clean, comfortable, easy to move around and enjoy the day. We caught real nice fish, Captain was very knowledgeable. I would recommend Captain Nick and would use him again.

    Ken C. | May 18, 2024

    Trip: Reel Salty Sportfishing

  • ★★★★★
    Captain Wade was great. Worked hard and put me in lots of fish! Will definitely call him again!

    Brian G. | May 8, 2024

    Trip: Tampa Bay Inshore Adventures

  • ★★★★★
    Nick was an amazing captain! He got us on some fish right away! We had a great time!

    Chris S. | April 26, 2024

    Trip: Reel Salty Sportfishing

  • ★★★★★
    Had a great half day out on the water with Hank. Very friendly and done a good job of keeping us on the fish.

    Brian W. | April 22, 2024

    Trip: 4-8 Hour Fishing Trip

Other Fishing Species in Holiday

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What's biting in Holiday?

View Sheepshead Fishing Reports from our damn good guides.

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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 Holiday