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 Charter in Key West

Southernmost Mahi Offshore Fishing

100% (3) Guided by Garrett
29 ft 1 - 6 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Key Largo

Key Largo Reef And Offshore

100% (1) Guided by Jim
34 ft 1 - 5 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter in Stock Island

Key West Nearshore/Offshore Trip

100% (6) Guided by Mike
63 ft 1 - 12 People From $1,850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Key West

Key West Offshore Action

89% (9) Guided by John
33 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, Nearshore Fishing Charter in Key West

Key West Mixed Bag Trip

100% (8) Guided by Brad
43 ft 1 - 6 People From $950
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 Charter in Islamorada

Offshore Thrills

94% (16) Guided by Paul
40 ft 1 - 12 People From $1,100
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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.”

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More 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 Charter in Islamorada

Ultimate Offshore Thrills

94% (16) Guided by Paul
40 ft 1 - 6 People From $1,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter in Key West

Legendary Fishing In Key West

100% (8) Guided by Chuck
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, Nearshore Fishing Charter in Key West

Key West Sportfish Trip

94% (18) Managed by Mark
37 ft 1 - 6 People From $1,150
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 Charter in Key West

Key West Fishing Slam

94% (18) Managed by Mark
36 ft 1 - 6 People From $1,050
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 Charter in Key West

Dawn To Dusk Key West Fishing Trip

100% (8) Guided by Brad
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 Fishing Charter in Key West

Full Day Offshore - 30' Seahunter

100% (18) Guided by Hunter
30 ft 1 - 6 People From $1,200
See All Sailfish Trips in the Florida Keys

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Everything to Know About Booking a Florida Keys sailfish fishing charter

What are the best sailfish fishing charters in the Florida Keys?

The best sailfish fishing charters in the Florida Keys are:

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

Our Damn Good Guides currently offer 45 sailfish trips in the Florida Keys, and the most popular trips in the area are Southernmost Mahi Offshore Fishing guided by Garrett, Key Largo Reef and Offshore guided by Jim, and Key West Nearshore/Offshore Trip guided by Mike.

Our guides in the Florida Keys are rated a 4.93 out of 5 based on 3716 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 $2,700, but the average price for a half day trip for sailfish in the Florida Keys is $1,339. The average price for a full day trip for sailfish in the Florida Keys is $1,965.

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

  • ★★★★★
    We had a blast with Joe and Captain Chuck. Will definitely return!

    Yohannes H. | October 28, 2024

    Trip: Legendary Fishing in Key West

  • ★★★★★
    We had such a great time and our guide was fun, knowledgeable, and put us on the fish all trip! We will be going back for sure.

    Rae S. | October 6, 2024

    Trip: Key West Offshore Action

  • ★★★★★
    Captain Steve and mate Stan are the best they put us on the fish and we will definitely be back

    Jason R. | September 25, 2024

    Trip: Key West Sportfishing Adventure

  • ★★★★★
    Excellent guide and first mate. Both were great. Stayed over our time to be sure all the kids caught something. Highly recommend!!!

    Graham S. | September 16, 2024

    Trip: Key West Fishing Slam

  • ★★★★★
    Chris & Will were great. Knowledgeable, professional, engaging and put us on the fish. Would highly recommend this charter.

    Doug B. | September 11, 2024

    Trip: Key West Sportfish Trip

  • ★★★★★
    We had an amazing time! We had a special interest in Mahi and captain brad and his first mate made it happen. It was great, they made us feel super comfortable and confident. We were able to score Mackerel, Yellowtail and we latched on 3 Mahi’s at the very very last second! Super lucky. Brad and his first mate made it happen! We were able to leave with 2 mackerels and 2 Mahi Mahi’s! Thank you! You won’t regret booking with them. Special experience.

    María A. | September 2, 2024

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    Captain Brad and his first mate were amazing. It was my first time fishing off of a boat and I'm glad it was with them! They were both very patient, helpful, and made it an unforgettable experience. We caught snapper and grouper and even hooked an eel! Thanks to both of you for a fantastic time on the water. Highly recommend

    Karen E. | August 19, 2024

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    Steve and woody were absolutely a load of fun although the fish were not biting they continued to try !! Very enjoyable time !

    Marcie R. | August 17, 2024

    Trip: Key West Fishing Slam

  • ★★★★★
    Absolutely the highlight of our trip. Mike and his crew were fantastic teachers, patient and focused on helping all of us catch terrific fish. They are great with kids of all ages - 5 years to 16 years. Everyone had a great time and we caught a lot of fish.

    Vicki L. | July 16, 2024

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    Was a great trip, got on some nice fish. Got surprised by a large school of smaller mahi mahi but had fun with the instant hook up and seemed to last a good bit. Captain was great, very knowledgeable and supplied drinks if we needed any. The boat was clean and spacious for the both of us and had plenty of rods in the water.

    Tony P. | July 12, 2024

    Trip: Full Day Offshore - 30' Seahunter

  • ★★★★★
    Fantastic trip with Capt. Joel and Darren. Got us on some great Mahi Mahi, and kept at it for the whole trip. Highly recommended.

    David L. | July 8, 2024

    Trip: Marathon Offshore - 30’ Grady White

  • ★★★★★
    My wife and I did a mix of reef fishing and offshore fishing to make an 8 hour trip. The bite was spotty at times, but we found a few schools of mahi mahi and were able to catch several of them throughout the day! We only had one keeper size, but it was very exciting to get into them and watch them hit our baits. Captain Steve and first mate Mike worked nonstop to get us into more fish. They can’t control if the fish will bite, but they certainly gave it their best effort. They also had great hospitality and offered plenty of fun stories and advice. We took our fresh catch to Lazy Days that evening and had an incredible dinner.

    Cooper S. | June 27, 2024

    Trip: Marathon Key Nearshore Run

  • ★★★★★
    The family had an absolutely phenomenal time with Captain Mike and his crew. We caught plenty of fish. The crew was very helpful to the family. The boat was great. I will 100% recommend them to anyone looking for a great trip.

    Tommy L. | June 25, 2024

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    My son, friend and i went out on Cowboy II with Captain Mark and Best Mate Ever Anthony. The Captain has eagle eyes and Anthony moves like an octopus, neither would give up until we CRUSHED IT. 2 Black Tail Tuna and 9 Mahi later we were happy as fishing guys could be. I am happy to recommend them for your trip with the guys. Enjoy Paul Cella

    Paul C. | June 24, 2024

    Trip: Key West Fishing Slam

  • ★★★★★
    Captain Brad and his deck hand Dennis was awesome given the weather and seas where not very good they still put us on fish and took care of us perfectly. Boat was very nice clean had lots of room (perfect set up) . Would highly recommended Captain Brad !!!!

    Johnny E. | June 23, 2024

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    Awesome experience. Captain chuck and Joe Joe were great. Nice boat, good times

    Stephen M. | June 22, 2024

    Trip: Legendary Fishing in Key West

  • ★★★★★
    Captain Mike and his crew were amazing!! We went out with 5 kids all under the age of 16 and they all caught fish and had a blast!! Blind Squirrel Rocks!!

    Fred S. | June 17, 2024

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    Had a fantastic day! Very relaxing and caught los of fish on the Cowgirl. The mate recommended the boathouse to take some of our catch for the restaurant to cook…Wow it was cooked to perfection!!

    Gene P. | June 15, 2024

    Trip: Key West Fishing Slam

  • ★★★★★
    Awesome day on the water today - Capt Steve put us on the fish and Stan kept us reeling with many triple hookups. Wore my boys out. Appreciate all the knowledge they shared too. Tight lines!

    Danny C. | June 8, 2024

    Trip: Key West Sportfishing Adventure

  • ★★★★★
    Was a great trip, while we didn't get all we wanted the crew worked there butt off!!! Would for sure book through them again!!

    Travis Z. | May 29, 2024

    Trip: Key West Sportfish Trip

Other Fishing Species in the Florida Keys

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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