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

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

Full Day Offshore - 30' Seahunter

100% (93)
30 ft 1 - 6 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Offshore Trip

NEW
38 ft 1 - 6 People From $1,800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Flats in Big Pine Key

4 Hr (pm)

100% (5)
27 ft 1 - 8 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Key West

Key West Sportfishing Adventure

100% (6)
34 ft 1 - 6 People From $1,050
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Layton

Layton Fishing Adventure

100% (6)
27 ft 1 - 4 People From $850
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

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

Gulf - Shrimp Boats & Wrecks

96% (27)
32 ft 1 - 6 People From $2,250
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

Mahi / Offshore Combo

100% (14)
35 ft 1 - 6 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, Nearshore Fishing in Key West

Marquesas Key Fishing Adventure

100% (19)
33 ft 1 - 4 People From $1,600
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Tavernier

3-6 Hr Offshore Or Reef Trip

NEW
30 ft 1 - 12 People From $650
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore, Flats Fishing in Key West

Reefs, Bays, Or Backcountry

100% (18)
25 ft 1 - 4 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key Colony Beach

Offshore Fishing Trip

NEW
32 ft 1 - 6 People From $1,500
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 52 sailfish trips in the Florida Keys, and the most popular trips in the area are Full Day Offshore - 30' Seahunter guided by Hunter, Offshore Trip guided by Todd, and 4 Hr (pm) guided by Chris.

Our guides in the Florida Keys are rated a 4.94 out of 5 based on 6351 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 $1,050 to $3,600, but the average price for a half day trip for sailfish in the Florida Keys is $1,555. The average price for a full day trip for sailfish in the Florida Keys is $2,343.

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

  • ★★★★★
    Bobby and Jason were extremely knowledgeable about fishing in the FL Keys. They worked diligently to get us fish on but it was not to be on this trip. As it has been said that’s why they call it fishing and not catching. It certainly wasn’t due to a lack of effort from the crew.

    Brian B. | February 22, 2026

    Trip: Sailfish / Edge Of Reef

  • ★★★★★
    Captain George was the most knowledgeable of local water ways, weather, boats and ocean species. I have been on several charters and George is top-ranked in friendly, and responsible. George provided an excellent charter.

    Melissa K. | February 17, 2026

    Trip: Layton Fishing Adventure

  • ★★★★★
    Paul was fantastic with communication and very accommodating. Originally scheduled to go out on Saturday but he contacted me ahead of time with some ocean condition concerns and we were able to move it to Sunday which was much calmer seas and a super pleasant experience on the water. Large boat with tons of room for our party of 4. Nice covered area and table for eating and getting a little reprieve from the sun. Unfortunately we didn't get into any sailfish that day but thats the way of the water and how fishing goes sometimes. We did get a couple king fish that Paul fileted up for us at the dock and still sent us home with a bunch of fresh fish that we were able to grill up that night.

    Dean G. | January 26, 2026

    Trip: Ultimate Offshore Thrills

  • ★★★★★
    Great trip Knowledge Captain and mate (Nels and CJ). Put us on the fish we targeted and mixed in a few othe rigs for variety. 5 stars, would do again.

    Tim R. | January 9, 2026

    Trip: Key West 47 Ft Hatteras

  • ★★★★★
    Captain Steve was excellent! We enjoyed fishing! He worked hard to put us on some quality fish! We had a top notch experience!

    Lynde U. | December 30, 2025

    Trip: Marathon Key Offshore - 32’ Morgan

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