Damn Good Sailfish Fishing Charters In Cudjoe Key

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

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Recently Booked Sailfish Fishing Charters In Cudjoe Key, Fl

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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
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, Jetty in Key West

Ultimate Action Fishing In Key West

100% (19)
33 ft 1 - 12 People From $800
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

Inshore, Deep Sea, Nearshore in Key West

Fishing - Private 3/4 Day Charter

100% (8)
28 ft 1 - 4 People From $1,050
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Marathon Offshore Slam- 50’ Bertram

100% (17)
50 ft 1 - 6 People From $1,895
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% (109)
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, Nearshore Fishing in Key West

Dry Tortugas Fishing Trip

100% (12)
36 ft 1 - 6 People From $2,800

Top Types of Sailfish Trips in Cudjoe Key

“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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All Target Species in Cudjoe Key

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)

More Sailfish Fishing Charters In Cudjoe Key, Fl

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 Sportfish Trip

99% (109)
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 in Key West

Key West Mixed Bag Trip

100% (36)
43 ft 1 - 6 People From $950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Sport Fishing Key West

NEW
42 ft 1 - 6 People From $1,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Full Day Private Fishing Charter

94% (18)
25 ft 1 - 4 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 Marathon

Deep Sea Combo (Swordfishing)

100% (14)
35 ft 1 - 6 People From $2,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Marathon Deep Dropping | 40'

100% (16)
40 ft 1 - 6 People From $1,995
See All Sailfish Trips in Cudjoe Key

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Everything to Know About Booking a Cudjoe Key sailfish fishing charter

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

Our Damn Good Guides currently offer 72 sailfish trips in Cudjoe Key, and the most popular trips in the area are All-Inclusive Fishing Adventure guided by Jose, Ultimate Action Fishing In Key West guided by Anthony, and Fishing - Private 3/4 Day Charter guided by Paulie.

Our guides in Cudjoe Key are rated a 4.93 out of 5 based on 6411 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 Cudjoe Key? Check out our beginner and family friendly sailfish guides in Cudjoe Key.

What types of sailfish fishing charters are common in Cudjoe Key?

Deep Sea fishing is the most popular type of fishing for sailfish in Cudjoe Key as well as inshore fishing and nearshore fishing.

The most common fishing techniques in Cudjoe Key are bottom fishing, deep dropping, and live bait fishing but trolling is popular as well.

How much do Cudjoe Key sailfish fishing charters cost?

Prices for sailfish in Cudjoe Key can range anywhere from about $1,200 to $4,000, but the average price for a half day trip for sailfish in Cudjoe Key is $1,570. The average price for a full day trip for sailfish in Cudjoe Key is $3,100.

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 Cudjoe Key?

The most popular season for sailfish fishing in Cudjoe Key is summer, and most anglers book their trips 10 days in advance.

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

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

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

  • ★★★★★
    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

  • ★★★★★
    Chris was AWESOME!!! Caught a ton of fish.

    Daniel H. | December 24, 2025

    Trip: Half Day (4hr)

  • ★★★★★
    If I could give Capt. Bill more than 5 stars I would. He is an exceptional professional and master of his trade. I booked a 1/2 day on Capt Bill’s boat with my two sons 15 and 12. Bill was an exceptional instructor taking the extra time to teach the nuance of how to be successful catching fish. Book a trip with Bill you will not be disappointed.

    Rick T. | December 21, 2025

    Trip: Sportfishing Half Day

Other Fishing Species in Cudjoe Key

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What's biting in Cudjoe Key?

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See All Sailfish Trips in Cudjoe Key