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

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore Fishing Charter 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 Fishing Charter near Cudjoe Key

Sailfish / Edge Of Reef

100% (2)
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

Inshore, Deep Sea, Nearshore Fishing Charter near Cudjoe Key

Fishing - Private 3/4 Day Charter

100% (2)
28 ft 1 - 4 People From $1,050
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore, Flats Fishing Charter near Cudjoe Key

Reefs, Bays, Or Backcountry

100% (8)
25 ft 1 - 4 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter near Cudjoe Key

Full Day Private Fishing Charter

88% (8)
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, Nearshore Fishing Charter near Cudjoe Key

Key West Sportfish Trip

95% (20)
37 ft 1 - 6 People From $1,150

Top Types of Sailfish Trips in Cudjoe Key

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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, Jetty Fishing Charter near Cudjoe Key

Key West Offshore - '27 CC

100% (34)
27 ft 1 - 12 People From $700
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 near Cudjoe Key

Deep Sea Combo (Swordfishing)

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

Deep Sea, Nearshore Fishing Charter near Cudjoe Key

Ultimate Action Fishing

NEW
30 ft 1 - 12 People From $900
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 near Cudjoe Key

Top Notch Offshore Pelagics

100% (3)
31 ft 1 - 6 People From $1,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter near Cudjoe Key

Marathon Key Offshore - 32’ Morgan

100% (8)
32 ft 1 - 6 People From $1,300
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 near Cudjoe Key

Dry Tortugas Fishing Trip

100% (3)
36 ft 1 - 6 People From $2,800
See All Sailfish Trips in Cudjoe Key

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Everything to Know About Booking a Cudjoe Key sailfish fishing charter

What are the best sailfish fishing charters in Cudjoe Key?

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

Our Damn Good Guides currently offer 62 sailfish trip in Cudjoe Key: All-Inclusive Fishing Adventure guided by .

Our guides in Cudjoe Key are rated a 4.92 out of 5 based on 4407 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, flats fishing, and nearshore fishing.

The most common fishing techniques in Cudjoe Key are live bait fishing, fly fishing, and light tackle fishing but drift fishing and trolling are popular as well.

How much do Cudjoe Key sailfish fishing charters cost?

Prices for sailfish in Cudjoe Key can range anywhere from about $1,100 to $3,045, but the average price for a half day trip for sailfish in Cudjoe Key is $1,504. The average price for a full day trip for sailfish in Cudjoe Key is $2,179.

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

  • ★★★★★
    Captain Antonio and his son did a great job. Weather/wind was not ideal but they made sure we had a great experience and we caught some fish!

    Jordan G. | April 24, 2025

    Trip: Offshore Fishing,Reef & Wreck and Sunset

  • ★★★★★
    Captain Josh did a great job putting us on fish. Very enjoyable day. Certainly would contact him for future trips.

    Jeff W. | April 16, 2025

    Trip: Offshore Trolling and Bottom Fishing

  • ★★★★★
    We had a great time on the water with captain Tony! He led us right to the fish! He is absolutely an expert in his craft! We would definitely fish with him again!

    Jessica N. | April 2, 2025

    Trip: Key West Offshore - '27 CC

  • ★★★★★
    awesome trip, polite friendly, clean would recommend and will be calling again

    Carol T. | March 24, 2025

    Trip: Key West Offshore - '27 CC

  • ★★★★★
    We had a great time with mason-fun day on the water

    Blaine W. | March 19, 2025

    Trip: Dry Tortugas fishing Trip

  • ★★★★★
    Had a great day on the water with Capt. Tony

    Chris S. | March 19, 2025

    Trip: Key West Offshore - '27 CC

  • ★★★★★
    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

  • ★★★★★
    My wife and I had a wonderful day of fishing with Capt.Chris. The bite was a little slow but Chris never gave up on finding fish and it turned into a good day of catching! Made for a great day on the water.

    John G. | March 12, 2025

    Trip: Half day (4hr)

  • ★★★★★
    Awesome day! The Fish had no chance! The Yellowtail and Mahi wore us out reeling them in. Great Captain, great fish, great experience! We will be booking again on our next visit.

    Christopher K. | March 6, 2025

    Trip: Offshore Fishing,Reef & Wreck and Sunset

  • ★★★★★
    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

  • ★★★★★
    Captain Joel did a fantastic job under adverse conditions! Put us on fish, and we caught our bucket list barracuda! Todd is by far one of the best mates I have fished with in 40 years! Good bedside manner. Thanks a million! Paul T

    Paul T. | February 26, 2025

    Trip: Marathon Offshore - 30’ Boca Grande

  • ★★★★★
    My son and I went out for two days with Hans and Adam. It could not have been a better experience. Great times, great people, great fishing. I would recommend them for anyone looking for a family fishing experience.

    Robert C. | February 21, 2025

    Trip: Key West Fishing Slam

  • ★★★★★
    We had an amazing trip with Captain Tony. He was super knowledgeable, kind and patient with a new young angler. He put us directly on fish and specifically the tuna we wanted. We will fish with Tony again for sure. If you are looking for guide, Tony is the man and knows the Key West waters and area well being born and raised in Key West.

    Britt B. | February 18, 2025

    Trip: Offshore Fishing,Reef & Wreck and Sunset

  • ★★★★★
    We had a wonderful afternoon fishing with Antonio and Tony!! Very pleasant and attentive, constantly moving to find us the best spots. Went above and beyond to ensure we caught fish, even on a slow day. Would highly recommend

    Rodney G. | February 9, 2025

    Trip: Offshore Fishing,Reef & Wreck and Sunset

  • ★★★★★
    captain hunter was awesome and courteous- and accommodating being a couple of newbies to fishing we learned a few things. I would recommend Captain hunter to everyone, and would enjoy going on another trip with him again.

    Hans-Jurgen G. | February 9, 2025

    Trip: Full Day Offshore - 30' Seahunter

  • ★★★★★
    Had a great trip with Brad. He was prompt and polite, but most importantly, a very attentive and experienced captain. He gave us many options for our outing and let us determine the course of our day. Highly recommend!

    Curtis C. | January 10, 2025

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    Captain Anthony was awesome! Great with the kids and adults alike. The weather wasn't cooperating on our trip but he still managed to put us some fish even if wasn't our target for the day. I would fish with Captain Anthony again anytime!

    Jb H. | January 7, 2025

    Trip: Ultimate Action Fishing in Key West

  • ★★★★★
    Joel was a great Captain was constantly on the hunt and gave great tips for each species. Todd was a great first mate took great care of us through the whole trip.

    Craig B. | December 27, 2024

    Trip: Marathon Offshore - 30’ Boca Grande

  • ★★★★★
    Brad and his first mate were first class. Helped us fish for all different kinds of fish. We even caught a 6 foot sailfish! Our family had a very nice time and highly recommend Captain Brad!

    Michael V. | December 25, 2024

    Trip: Key West Mixed Bag Trip

What's biting in Cudjoe Key?

View Sailfish Fishing Reports from our damn good guides.

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