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

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Marathon Offshore - 30’ Boca Grande

100% (16)
30 ft 1 - 6 People From $1,000
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Marathon Sportsfishing Trip

100% (1)
45 ft 1 - 6 People From $950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Islamorada

Offshore Fishing Experience

100% (1)
36 ft 1 - 6 People From $1,000
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 Islamorada

Offshore Thrills

99% (69)
40 ft 1 - 12 People From $1,100
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Cudjoe Key

All-Inclusive Fishing Adventure

100% (1)
34 ft 1 - 6 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Layton

Layton Fishing Adventure

100% (5)
27 ft 1 - 4 People From $850

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 Largo

Key Largo Offshore Mixed Bag

100% (10)
35 ft 1 - 6 People From $1,400
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

Deep Sea Fishing in Marathon

Deep Sea Combo (Swordfishing)

100% (9)
35 ft 1 - 6 People From $2,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Marathon

Nearshore Expedition

100% (3)
35 ft 1 - 5 People From $900
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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Offshore Fishing Trip

NEW
31 ft 1 - 6 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Key West Offshore Action

96% (27)
32 ft 1 - 6 People From $1,000
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 49 sailfish trips in the Florida Keys, and the most popular trips in the area are Marathon Offshore - 30’ Boca Grande guided by Joseph, Marathon Sportsfishing Trip guided by Jay, and Offshore Fishing Experience guided by Thomas.

Our guides in the Florida Keys are rated a 4.94 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 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, inshore fishing, and flats 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 $2,600, but the average price for a half day trip for sailfish in the Florida Keys is $1,353. The average price for a full day trip for sailfish in the Florida Keys is $1,943.

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 summer, and most anglers book their trips 20 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

  • ★★★★★
    Wonderful trip, they made it so easy to enjoy ourselves, crew was inviting and welcoming. will definitely be booking again

    Heather W. | November 27, 2025

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    We took our team out with Hunter for a combo lobstering and deep sea trip and he didn't let us down! First and foremost, Hunter is an ex-marine who is incredibly on top of his equipment, his boat, and his safety and was very clear about expectations for the day and what we should be doing at any point in time. After a quick scuba diving refresher & safety brief we put on our gear for a dive and were rewarded with a number of keeper lobsters, a bigger number of lobsters that were too small to keep, a lionfish which we speared, and too many great wildlife sightings to count including a big loggerhead turtle, a black grouper, and a nurse shark hoping for a handout. After the dive we put our gear away we drove a few miles further out to catch some yellowtail snapper. We started slow, but pretty soon were reeling in a yellowtail almost every cast. We probably caught 20-25 within a few hours, as well as a small yellow jack, a parrotfish, and an undersized red grouper. Lastly, we decided to use the last hour of our trip to try to hook into a big black grouper using some of our yellowtail as bait. This was a bit of a "go big or go home" bet and unfortunately didn't pay off for us this time - I wish we'd had a bit more time to drift and I'm sure we would have hooked one. Overall can't speak highly enough of Hunter and the experience diving and fishing in the Keys. There is such a variety of things to do that even on a full day trip you will never feel bored and can always pivot to something else. We even chased a frigate bird and threw some bucktails in the middle of the day at some bait that was busting. You won't go wrong booking a trip with Hunter.

    Attison B. | November 5, 2025

    Trip: Full Day Offshore - 30' Seahunter

  • ★★★★★
    Awesome trip Captain Brad put us on the fish all day

    Sam R. | November 2, 2025

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    Paul and first mate Gary worked hard all day on our 8 hour trip offshore. Targeting Blackfin Tuna, Mackerel and Sailfish all day and keeping us over the fish with consistent bites. Would definitely recommend to anybody who wants a good experience offshore and will hopefully be back again in the future.

    Adam T. | October 13, 2025

    Trip: Ultimate Offshore Thrills

  • ★★★★★
    Captain Brad did a great job! Very good boat.

    Jeff M. | October 13, 2025

    Trip: Key West Mixed Bag Trip

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See All Sailfish Trips in the Florida Keys