Damn Good Sailfish Fishing Charters In Stock Island

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

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Recently Booked Sailfish Fishing Charters In Stock Island, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Stock Island

Key West Offshore Experience

100% (4)
42 ft 1 - 6 People From $1,200
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Stock Island

Key West Nearshore/Offshore Trip

100% (34)
63 ft 1 - 12 People From $1,850
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
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
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 Big Pine Key

Big Pine Offshore Fishing

100% (3)
25 ft 1 - 12 People From $1,150
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

Top Types of Sailfish Trips in Stock Island

“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.”

Jonathan and Attison   |   Co-founders   |   Austin, Texas

All Target Species in Stock Island

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 Stock Island, 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 Fishing in Key West

Sportfishing Key West

100% (8)
50 ft 1 - 12 People From $950
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 Key West

Key West Deep Sea Fishing (Private)

100% (9)
46 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 Key West

Dawn To Dusk Key West Fishing Trip

100% (36)
43 ft 1 - 6 People From $2,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore, Flats Fishing in Key West

Reefs, Bays, Or Backcountry

100% (18)
25 ft 1 - 4 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Offshore, Reef & Wreck, And Sunset

100% (134)
36 ft 1 - 12 People From $900
See All Sailfish Trips in Stock Island

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Everything to Know About Booking a Stock Island sailfish fishing charter

Why should I book a sailfish fishing charter in Stock Island with Captain Experiences?

Our Damn Good Guides currently offer 50 sailfish trips in Stock Island, and the most popular trips in the area are Key West Offshore Experience guided by Chris, Key West Nearshore/Offshore Trip guided by Mike, and Offshore Fishing Trip guided by Tyler.

Our guides in Stock Island are rated a 4.92 out of 5 based on 6906 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 Stock Island? Check out our beginner and family friendly sailfish guides in Stock Island.

What types of sailfish fishing charters are common in Stock Island?

Deep Sea fishing is the most popular type of fishing for sailfish in Stock Island as well as nearshore fishing.

The most common fishing techniques in Stock Island are light tackle fishing, artificial lure fishing, and drift fishing but heavy tackle fishing and jigging are popular as well.

How much do Stock Island sailfish fishing charters cost?

Prices for sailfish in Stock Island can range anywhere from about $1,200 to $4,000, but the average price for a half day trip for sailfish in Stock Island is $1,595. The average price for a full day trip for sailfish in Stock Island is $3,283.

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 Stock Island?

The most popular season for sailfish fishing in Stock Island is summer, and most anglers book their trips 21 days in advance.

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

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

Recent Reviews

  • ★★★★★
    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

  • ★★★★★
    Awsome time !!!

    David T. | March 16, 2026

    Trip: Private Offshore Fishing

  • ★★★★★
    I wish that I could give Joel and Tony more than 5 stars. We left the fishing trip with only 1 complaint and that was that we only booked it for 1 day. We absolutely will be back!!!

    Christopher C. | March 11, 2026

    Trip: Private Offshore Fishing

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What's biting in Stock Island?

View Sailfish Fishing Reports from our damn good guides.

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See All Sailfish Trips in Stock Island