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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing Charter near Holiday

Clearwater Inshore Special

100% (2) Guided by Jim
27 ft 1 - 6 People From $505
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing Charter near Holiday

The Reel Shindig

NEW Guided by Sebastian
17 ft 1 - 4 People From $300
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

Sight Fishing TB - Artificials, Fly Or Bait!

NEW Guided by Paul
19 ft 1 - 6 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing Charter near Holiday

St. Petersburg Inshore Slam

100% (1) Guided by Andy
25 ft 1 - 4 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing Charter near Holiday

Inshore Fishing Treasure Island

NEW Managed by Joey
23 ft 1 - 4 People From $550
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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 $400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing Charter near Holiday

Tampa Bay Inshore/Nearshore Classic

NEW Guided by Joe
23 ft 1 - 6 People From $650
Fishing in Destin
Fishing in Destin
Fishing in Destin

Flats Fishing Charter near Holiday

Family Bowfishing Outing

100% (3) Guided by Ike
22 ft 1 - 6 People From $600
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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing Charter near Holiday

Fly Fishing Charters

NEW Guided by Gage
18 ft 1 - 2 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats Fishing Charter near Holiday

Fisherman's Choice Trip

NEW Guided by Garrett
22 ft 1 - 4 People From $550
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 31 sheepshead trip in Holiday: Half Day Trip (4hrs) guided by Carlos.

Our guides in Holiday are rated a 5 out of 5 based on 3920 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 cut bait fishing and bottom 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 $1,300, but the average price for a half day trip for sheepshead in Holiday is $680. The average price for a full day trip for sheepshead in Holiday is $937.

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

  • ★★★★★
    Great day on the water with Captain Hank and his son. Fishing was excellent. Would definitely recommend Captain Hank for a day of fishing.

    Thomas H. | January 7, 2025

    Trip: 4-8 Hour Fishing Trip

  • ★★★★★
    Great night out with Captain Ike. Very patient and knowledgeable. Will be back next year for more then the 4 hour trip. Put us on plenty of fish with tons of shots.

    Jeff J. | January 6, 2025

    Trip: Tampa Bowfishing

  • ★★★★★
    Had a great time on an inland trip with Robert. He was very professional and well prepared and we ended up getting exactly what we wanted. Will line him up the next time we are in town.

    Hilary C. | January 3, 2025

    Trip: In or Near Shore Experience

  • ★★★★★
    Great trip with a great captain!

    Adam G. | January 3, 2025

    Trip: Bowfishing the Tampa Bay

  • ★★★★★
    Capn Mike took us out and was very informative about how and why and where went went Ladyfish were plentiful. it was tougher for bigger fish. But thats the way fishing is. Capn MIke kept us out longer in hopes of getting something We appreciated that, All in all it was a good experience and we would do it again. Don B

    Donald B. | December 31, 2024

    Trip: St. Petersburg Inshore Slam

  • ★★★★★
    We had a great trip! The boat was very nice and spacious. Mike was great with the kids and teaching us how to fish. Not all of us were able to hit something, but we still had fun. We saw so much nature including dolphins that swam with us.

    Lindsay C. | December 28, 2024

    Trip: Bowfishing the Tampa Bay

  • ★★★★★
    We had an amazing time bowfishing with Captain Mike this past weekend. My 10 year old son and I had a blast learning how to fish with a bow, and translating shooting at paper targets into shooting at moving fish. The Bay was alive with marine life and it was really cool to be out there together. There was a small technical issue that came up early in the trip, but Captain Mike used his experience to quickly resolve it and get us back out to where the fish were jumping. We are definitely going to book with him again!

    Ryan M. | November 19, 2024

    Trip: Bowfishing the Tampa Bay

  • ★★★★★
    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!!!

  • ★★★★★
    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

  • ★★★★★
    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

Other Fishing Species in Holiday

Other Featured Cities

What's biting in Holiday?

View Sheepshead Fishing Reports from our damn good guides.

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 Holiday