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
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

Key West Deep Sea Fishing (Private)

100% (9)
46 ft 1 - 6 People From $1,100
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Offshore Fishing

100% (5)
33 ft 1 - 12 People From $1,150
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Gulf - Shrimp Boats & Wrecks

96% (28)
32 ft 1 - 6 People From $2,250
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Stock Island

Offshore Fishing Trip

NEW
25 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 in Marathon

Sportfishing Half Day

100% (15)
31 ft 1 - 6 People From $975

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

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Key West Offshore Action

96% (28)
32 ft 1 - 6 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Little Torch Key

3/4 Or Full Day Trip

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

Inshore, Deep Sea, Flats in Big Pine Key

Half Day (4hr)

100% (5)
27 ft 1 - 8 People From $800
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Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Stock Island

Key West Fishing More Than 6 Paxs

100% (34)
63 ft 1 - 12 People From $2,150
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Ultimate Angler's Paradise

100% (38)
40 ft 1 - 12 People From $2,200
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

4-8 Hour Offshore Trip

NEW
32 ft 1 - 6 People From $1,050
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 71 sailfish trips in Cudjoe Key, and the most popular trips in the area are All-Inclusive Fishing Adventure guided by Jose, Key West Deep Sea Fishing (Private) guided by Thomas, and Offshore Fishing guided by Aaron.

Our guides in Cudjoe Key are rated a 4.94 out of 5 based on 7092 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 $3,600, but the average price for a half day trip for sailfish in Cudjoe Key is $1,662. 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

  • ★★★★★
    I had a fantastic experience fishing with Captain Zac. He was professional and dialed in, getting us onto the fish immediately. We spent the day targeting Tarpon, Yellowtail Snapper, and Mutton Snapper with great success. A top-tier charter!"

    William A. | April 29, 2026

    Trip: Key West Offshore Excitement!

  • ★★★★★
    Had an excellent trip. There was not a lot of boats getting fish, but the Captain and his Mate kept working at it, and we both had success. Very enjoyable trip!

    Allen R. | April 7, 2026

    Trip: Offshore, Reef & Wreck, And Sunset

  • ★★★★★
    Sam and crew were very professional and diligent in trying to locate fish. Unfortunately due to rough seas in the days immediately preceding our excursion the wish were not biting. We went back in via the reef and picked up six yellow tail (skipjack) which made for good eating (bang-bang style) that evening. Would charter with Mark and team again.

    Ben B. | March 26, 2026

    Trip: Key West Deep Sea Run - 40' Luhrs

  • ★★★★★
    Anthony was great! Very informative, super helpful. I would absolutely go with Anthony again & again! Thanks Anthony!

    Claren N. | March 23, 2026

    Trip: Marquesas Key Fishing Adventure

  • ★★★★★
    Great day with Captain Bill on the water! We did a half day trip with my family and had a blast. My girls didn’t want rough seas so Bill took us out in the bay and we caught our limit of snapper with a couple of bonus trout. The highlight was the shark that tried to eat our snapper boat side! I would highly recommend Captain Bill and we will be giving him a call our next trip back to the Keys!

    Brian B. | March 19, 2026

    Trip: Sportfishing Half Day

Other Fishing Species in Cudjoe Key

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What's biting in Cudjoe Key?

View Sailfish Fishing Reports from our damn good guides.

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