Damn Good Sheepshead Fishing Charters In Naples

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

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Recently Booked Sheepshead Fishing Charters In Naples, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, River, Flats in Naples

Inshore / Backwater Fishing

NEW
22 ft 1 - 8 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Naples

Weekend Getaway Day Trip

100% (7)
20 ft 1 - 4 People From $500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Naples

Southwest Florida Backwater Trip

100% (1)
23 ft 1 - 4 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Naples

Beginners Welcome - Fishing 101

100% (30)
24 ft 1 - 4 People From $650
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 Fishing in Naples

Weekday Afternoon Trip

100% (7)
20 ft 1 - 4 People From $500

Top Types of Sheepshead Trips in Naples

“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.”

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All Target Species in Naples

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 Naples, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Fort Myers Beach

Fort Myers Hook Up!

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

Inshore, Flats Fishing in Fort Myers

Fishing Thrills In Fort Myers

100% (4)
22 ft 1 - 4 People From $500
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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Marco Island

Goodland FL Fishing Trip

100% (4)
25 ft 1 - 3 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Fort Myers Beach

SWFL Inshore/Back Bay Fishing

100% (1)
22 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, Nearshore, Flats in Marco Island

3 - 4 Hour Inshore Fishing

94% (17)
25 ft 1 - 12 People From $475
See All Sheepshead Trips in Naples

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Everything to Know About Booking a Naples sheepshead fishing charter

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

Our Damn Good Guides currently offer 21 sheepshead trips in Naples, and the most popular trips in the area are Weekday Afternoon Trip guided by Stanley, Weekend Getaway Day Trip guided by Stanley, and 4 Hour Backwater/Nearcoastal guided by Steven.

Our guides in Naples are rated a 4.95 out of 5 based on 5156 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 Naples? Check out our beginner and family friendly sheepshead guides in Naples.

What types of sheepshead fishing charters are common in Naples?

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

The most common fishing techniques in Naples are fly fishing, artificial lure fishing, and drift fishing but live bait fishing and artificial lure fishing are popular as well.

How much do Naples sheepshead fishing charters cost?

Prices for sheepshead in Naples can range anywhere from about $550 to $1,900, but the average price for a half day trip for sheepshead in Naples is $871. The average price for a full day trip for sheepshead in Naples is $1,396.

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 Naples?

The most popular season for sheepshead fishing in Naples is spring, and most anglers book their trips 11 days in advance.

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

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

Recent Reviews

  • ★★★★★
    Captain Dalton did a great job and so knowledgeable of the area. His knowledge of the fish, areas to fish, is excellent. His old Florida mantra made the trip top notch. We will be looking for hIm on our next trip to FT. MYERS

    Ronald K. | July 5, 2025

    Trip: Fishing Thrills in Fort Myers

  • ★★★★★
    RICHARD WAS NOT ON OUR TRIP TODAY!

    Joseph E. | June 16, 2025

    Trip: Fort Myers Beach Fishing Charters

  • ★★★★★
    Great captain. Had an awesome time on the water. Will be returning for another trip

    Joe G. | April 26, 2025

    Trip: Marco Island Charter Fishing

  • ★★★★★
    Absolute blast with Captain Steve! We went a few miles offshore and fished for Goliath grouper. Caught several in the 30-50 lb range, one 85+ lb, one 185+ lb, and hooked a world class Goliath Grouper but ended up breaking the line on structure! Couldn’t recommend a better guide to go out and land some huge fish. We will definitely head out with Steve again when we come back to town, highly recommend!

    Derec S. | April 20, 2025

    Trip: Goodland FL Fishing Trip

  • ★★★★★
    Captain Cooper elevated our experience. I thought he’d be good when we started, by the end he was great. 6 star review if possible. Thank you captain Cooper and Company

    Marc M. | April 18, 2025

    Trip: 3 - 4 Hour Inshore Fishing

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