Damn Good Sailfish Fishing Charters In Clearwater

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

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Recently Booked Sailfish Fishing Charters In Clearwater, Fl

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Fishing in Destin
Fishing in Destin
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Deep Sea Fishing in Clearwater

"Offshore Extreme" Middle Grounds

100% (33)
42 ft 1 - 12 People From $2,000
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Clearwater

8 Hour Offshore Epic Fishing

100% (33)
42 ft 1 - 6 People From $1,600
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Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Nokomis

Nokomis Offshore/Nearshore

NEW
39 ft 1 - 6 People From $2,200
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Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Gulfport

Offshore Drag Ripper

100% (12)
31 ft 1 - 6 People From $1,970

“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

All Target Species in Clearwater

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)

Other Captain Experiences Trips in Clearwater

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Clearwater Mixed Bag Offshore

100% (57)
27 ft 1 - 6 People From $1,650
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Inshore, Nearshore, Flats in Clearwater

Clearwater Classic

100% (6)
21 ft 1 - 4 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
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Inshore, Flats Fishing in Tampa

Tampa Bay Fishing Classic

99% (90)
21 ft 1 - 4 People From $350
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Inshore, Nearshore, Flats in St. Petersburg

Inshore Fishing Trip AM

100% (12)
22 ft 1 - 3 People From $450
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Nearshore Fishing in Indian Rocks Beach

Indian Rocks Fishing Adventure

100% (3)
32 ft 1 - 6 People From $820
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
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Inshore, Nearshore Fishing in Clearwater

Tampa Bay Fishing - 22’ Aguasport

100% (18)
22 ft 1 - 4 People From $600
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Inshore, Nearshore, Flats in Clearwater

Coastal Clearwater Charter

100% (27)
24 ft 1 - 5 People From $550
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Inshore, Nearshore Fishing in St. Petersburg

Florida Snook, Jacks, And Reds

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

Inshore Fishing in St. Petersburg

Night Trip - 22' Skeeter

100% (7)
22 ft 1 - 4 People From $500
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
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Inshore, River Fishing in St. Petersburg

Inshore Fishing Excursion

100% (4)
24 ft 1 - 4 People From $500
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Deep Sea, Nearshore Fishing in St. Petersburg

Offshore Trip - 27' Cape Horn

100% (20)
27 ft 1 - 4 People From $550
Fishing in Destin
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Inshore Fishing in St. Petersburg

4-hour Inshore - 26 C-Hawk

100% (3)
26 ft 1 - 4 People From $600

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Everything to Know About Booking a Clearwater sailfish fishing charter

Why should I book a sailfish fishing charter in Clearwater with Captain Experiences?

Our Damn Good Guides currently offer 4 sailfish trips in Clearwater, and the most popular trips in the area are "Offshore Extreme" Middle Grounds guided by Tommy, 8 Hour Offshore Epic Fishing guided by Tommy, and Nokomis Offshore/Nearshore guided by Josh.

Our guides in Clearwater are rated a 5 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 sailfish guides / fishing lessons in Clearwater? Check out our beginner and family friendly sailfish guides in Clearwater.

What types of sailfish fishing charters are common in Clearwater?

Deep Sea fishing is the most popular type of fishing for sailfish in Clearwater as well as deep sea fishing and nearshore fishing.

The most common fishing techniques in Clearwater are bottom fishing, heavy tackle fishing, and trolling but artificial lure fishing and cut bait fishing are popular as well.

How much do Clearwater sailfish fishing charters cost?

Prices for sailfish in Clearwater can range anywhere from about $1,979 to $4,000, but the average price for a full day trip for sailfish in Clearwater is $3,143.

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 sailfish fishing in Clearwater?

The most popular season for sailfish fishing in Clearwater is summer, and most anglers book their trips 22 days in advance.

Do I need a Clearwater fishing license for sailfish and what are the bag limits for sailfish in Clearwater?

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

Recent Reviews

  • ★★★★★
    We had a great time 12 hour trip Captain Tommy was great very knowledgeable .Alex (sweetie) lol inside joke he did a great job keeping our rods baited and taking off the fish over all could not have asked for for anymore!

    Ronnie H. | September 28, 2025

    Trip: "Offshore Extreme" Middle Grounds

  • ★★★★★
    Awesome is an understatement!!! As a Florida born, Clearwater native, salt water addict, life long fisherman, I can’t say enough about this trip. I’ve always owned boats and I’ve never taken a guided trip, as a native it feels like blasphemy. Captain Tommy is a blast to be around, a wealth of knowledge, and as passionate about fishing as anyone I’ve ever met. He’s driven by his desire to deliver results and be successful as a fisherman, it shows in every aspect of his service. He was as excited to put people on fish, as I think he might be to catch them for himself and that speaks volumes. He shares a lifetime of commitment to his passion, and everyone who’s fishing with Captain Tommy benefits. We caught stud fish all day! Don’t take my word for it. Pay the man and go fishing. Five stars isn’t enough.

    Stephen B. | September 21, 2025

    Trip: 8 Hour Offshore Epic Fishing

  • ★★★★★
    Tommy and Alex were fantastic! Very laid back yet professional the entire trip. They put us on some nice American Reds and a few nice grouper, as well as, a ton of shorties that had to be thrown back. We could have had a lot more if those dang sharks were not everywhere, but we still filled the box. AND to end the day, we caught a diamondback rattler crossing the inlet. It was some kind of crazy and I am sure we will have a lasting memory for the rest of our lives… Thanks Tommy & Alex, we had a fantastic time and I look forward to hopefully booking again with you real soon!

    Edward B. | July 14, 2025

    Trip: 8 Hour Offshore Epic Fishing

  • ★★★★★
    We made a full 8 hr trip with Capt. Tommy and his mate Alex. Fishing started out hot but slowed down later in the day, but fishing on a full moon is never ideal. The boat was great, lots of room for the 6 of us to relax and fish comfortably. Tommy and Alex were very entertaining and were great with the 3 first time fishermen we had in our party. I highly recommend fishing with Capt. Tommy, we certainly will!

    Andrew M. | July 13, 2025

    Trip: 8 Hour Offshore Epic Fishing

  • ★★★★★
    If you are looking for a full ice box of fish and a great day on the water Captain Tommy is the best of the best. We caught just everything the gulf has to offer, Gag Grouper, Red Grouper, Red Snapper, Mango Snapper, Lane snapper, Porgy, and Mahi. He has a beautiful boat and great tackle, stop scrolling and go book him, you won’t be disappointed.

    George G. | July 7, 2025

    Trip: "Offshore Extreme" Middle Grounds

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What's biting in Clearwater?

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