Damn Good Sailfish Fishing Charters In The Florida Keys

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

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Recently Booked Sailfish Fishing Charters In The Florida Keys

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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

Deep Sea Fishing in Key West

Full Day Offshore - 30' Seahunter

100% (67)
30 ft 1 - 6 People From $1,200
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

Deep Sea Fishing in Key West

Dawn To Dusk Key West Fishing Trip

100% (30)
43 ft 1 - 6 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, Nearshore Fishing in Key West

Marquesas Key Fishing Adventure

100% (15)
33 ft 1 - 4 People From $1,600
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 Marathon

Deep Sea Combo (Swordfishing)

100% (5)
35 ft 1 - 6 People From $2,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Stock Island

Key West Offshore Experience

100% (4)
42 ft 1 - 6 People From $1,200
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

Deep Sea, Nearshore Fishing in Key West

Key West Fishing Experience

100% (4)
32 ft 1 - 8 People From $900

Top Types of Sailfish Trips in the Florida Keys

“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 Sailfish Fishing Charters In The Florida Keys

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Key West Big Game Fishing

100% (1)
34 ft 1 - 6 People From $1,500
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

Deep Sea, Nearshore Fishing in Key West

Key West Fishing Slam

99% (91)
36 ft 1 - 6 People From $1,050
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Ultimate Angler's Paradise

100% (32)
40 ft 1 - 12 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Marathon Offshore - 30’ Grady White

100% (12)
30 ft 1 - 6 People From $1,295
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Legendary Fishing In Key West

100% (25)
55 ft 1 - 6 People From $1,100
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

Deep Sea Fishing in Key Largo

Offshore Pelagics - 38’ Outer Banks

100% (13)
38 ft 1 - 6 People From $2,350
See All Sailfish Trips in the Florida Keys

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Everything to Know About Booking a Florida Keys sailfish fishing charter

Why should I book a sailfish fishing charter in the Florida Keys with Captain Experiences?

Our Damn Good Guides currently offer 47 sailfish trips in the Florida Keys, and the most popular trips in the area are Florida Keys Fishing Adventure guided by Casey, Ultimate Offshore Thrills guided by Paul, and Key Largo Offshore Fishing Trip guided by Andrew.

Our guides in the Florida Keys are rated a 4.94 out of 5 based on 4533 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 the Florida Keys? Check out our beginner and family friendly sailfish guides in the Florida Keys.

What types of sailfish fishing charters are common in the Florida Keys?

Deep Sea fishing is the most popular type of fishing for sailfish in the Florida Keys as well as nearshore fishing, flats fishing, and inshore fishing.

The most common fishing techniques in the Florida Keys are trolling, heavy tackle fishing, and bottom fishing but light tackle fishing and jigging are popular as well.

How much do Florida Keys sailfish fishing charters cost?

Prices for sailfish in the Florida Keys can range anywhere from about $1,000 to $2,625, but the average price for a half day trip for sailfish in the Florida Keys is $1,355. The average price for a full day trip for sailfish in the Florida Keys is $1,951.

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 the Florida Keys?

The most popular season for sailfish fishing in the Florida Keys is spring, and most anglers book their trips 23 days in advance.

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

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

Recent Reviews

  • ★★★★★
    We had a great drip with Joel and JoJo as our captains! Their first mates were fantastic and helpful getting us on some fish!

    Matt W. | April 28, 2025

    Trip: Marathon Offshore - 30’ Grady White

  • ★★★★★
    Amazing trip. All crew members were extremely kind, experienced and fun to be around 10/10 would go again

    Max G. | March 28, 2025

    Trip: Ultimate Offshore Thrills

  • ★★★★★
    Despite the unfortunate windy weather, Captain Joel and first mate Todd made for a great day. They worked hard to get us on fish, and we had. Great day! We ended up catching 10 different species (mostly snapper) had plenty to eat I would highly recommend this charter to anyone!

    Andy T. | March 19, 2025

    Trip: Marathon Offshore - 30’ Boca Grande

  • ★★★★★
    We really enjoyed our trip brad was very knowledgeable and helpful as was his deckhand very easygoing and professional I will be back soon to book with him again

    John D. | March 15, 2025

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    Great trip! The bite wasn’t great, but we were able to catch a few and got our targeted Mahi Mahi!

    April C. | March 3, 2025

    Trip: Key West Offshore Experience

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 Sailfish Trips in the Florida Keys