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 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 Key West

Ultimate Action Fishing

100% (2)
30 ft 1 - 12 People From $900
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 in Big Pine Key

Chase Giants From Big Pine Key

NEW
33 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

Legendary Fishing In Key West

100% (25)
55 ft 1 - 6 People From $1,100
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Marathon

Marathon Reef And Bride Adventure

100% (7)
29 ft 1 - 6 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Key West

6 Hour Private Fishing

100% (2)
28 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 Fishing in Key West

Offshore Fishing,Reef & Wreck And Sunset

100% (97)
35 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 in Key West

Full Day Offshore - 30' Seahunter

100% (71)
30 ft 1 - 6 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Stock Island

Key West Nearshore/Offshore Trip

100% (32)
63 ft 1 - 12 People From $1,850
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 Marathon

3/4 Day

100% (6)
34 ft 1 - 6 People From $1,600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Naval Air Station Key West

Nearshore 4-8 Hour

NEW
34 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 Fishing in Marathon

Top Notch Offshore Pelagics

100% (10)
31 ft 1 - 6 People From $1,400
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 64 sailfish trip in Cudjoe Key: All-Inclusive Fishing Adventure guided by Jose.

Our guides in Cudjoe Key are rated a 4.93 out of 5 based on 5144 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 $2,998, but the average price for a half day trip for sailfish in Cudjoe Key is $1,498. The average price for a full day trip for sailfish in Cudjoe Key is $2,180.

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

  • ★★★★★
    We had an awesome day with Captain Aaron. He dialed up the perfect weather. We caught a bunch of fish, including this 25 pound bull.

    Todd H. | July 14, 2025

    Trip: Offshore Fishing

  • ★★★★★
    We had an absolutely unforgettable day on the water with Captain Mason! Our family of six—ranging from more "seasoned" to children—was treated to a private fishing excursion that truly exceeded all expectations. From the moment we stepped on the boat, the Mason made us feel completely at ease. He was incredibly accommodating, making sure each of us was comfortable, engaged, and having a great time. Whether it was adjusting for the kids' needs, helping with baiting hooks, or offering fishing tips to the beginners among us, his patience and positive energy never wavered. What stood out the most was how safe and inclusive he made the entire experience. Every member of the family felt like part of the crew. He kept a watchful eye on everything while still creating a laid-back, fun atmosphere. We never once felt rushed or out of place—just fully present and enjoying every moment. He also went above and beyond in every possible way—from extending our time a bit when the fish were biting to showing us local wildlife and secret spots only a seasoned pro would know. It truly felt like a one-of-a-kind adventure curated just for us. Highly recommend this charter to anyone looking for a fun, family-friendly, and expertly guided day on the water. Can’t wait to book again next time we’re in town!

    Lee D. | July 10, 2025

    Trip: Dry Tortugas fishing Trip

  • ★★★★★
    Paulie was an awesome captain. I can’t say enough good things about him. We weren’t sure we’d find my dream dolphin fish since they were pretty scattered…captain Paulie found them and put us on em! The best fishing charter I’ve been on in a long time. I’d recommend him to everyone.

    Garon U. | June 22, 2025

    Trip: Fishing - Private 3/4 Day Charter

  • ★★★★★
    This adventure was absolutely fantastic! Antonio was a great captain and he made the trip to extra fun! Highly recommend him!

    Marianne K. | June 8, 2025

    Trip: Key West Offshore - '27 CC

  • ★★★★★
    I can only highly recommend Hunter - we booked a spearfishing trip out West and had an absolutely great time. Hunter knew the area inside out, is a great captain with lots of experience, had high quality gear, and we saw (and shot) a lot of fish, mostly grouper. Highly recommend and will be back!

    Raimund R. | June 8, 2025

    Trip: Full Day Offshore - 30' Seahunter

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What's biting in Cudjoe Key?

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