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.

Choose a Date
4.91/5 Average Rating

Damn Good Guides

You will only find quality, vetted guides on Captain Experiences, and we know them all on a first-name basis

Experts Available 24/7

Our US-based team is available 24/7 to help you with any questions or concerns

100% Weather Guarantee

We want to keep everyone safe, so in the case of inclement weather we'll work with you to reschedule at no cost

Recently Booked Sailfish Fishing Charters In Stock Island, Fl

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

Key West Offshore Experience

100% (4)
42 ft 1 - 6 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Southernmost Mahi Offshore Fishing

100% (19)
29 ft 1 - 6 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, Jetty in Key West

Key West Offshore - '27 CC

100% (125)
27 ft 1 - 8 People From $700
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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Offshore Fishing Trip

NEW
31 ft 1 - 6 People From $900

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

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Dry Tortugas Smash

96% (27)
32 ft 1 - 6 People From $2,400
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

Deep Sea Fishing in Key West

Full Day Offshore - 30' Seahunter

100% (87)
30 ft 1 - 6 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 Key West

Sportfishing Key West

100% (8)
50 ft 1 - 12 People From $950
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 47 Ft Hatteras

99% (106)
47 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 Key West

Key West Fishing Slam

99% (106)
36 ft 1 - 6 People From $1,050
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Gulf - Shrimp Boats & Wrecks

96% (27)
32 ft 1 - 6 People From $2,250
See All Sailfish Trips in Stock Island

Need a Place to Stay?

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 45 sailfish trips in Stock Island, and the most popular trips in the area are Key West Nearshore/Offshore Trip guided by Mike, Key West Offshore Experience guided by Chris, and Southernmost Mahi Offshore Fishing guided by Garrett.

Our guides in Stock Island are rated a 4.91 out of 5 based on 5945 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 deep sea fishing, nearshore fishing, and jetty fishing.

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

How much do Stock Island sailfish fishing charters cost?

Prices for sailfish in Stock Island can range anywhere from about $1,150 to $3,215, but the average price for a half day trip for sailfish in Stock Island is $1,520. The average price for a full day trip for sailfish in Stock Island is $3,258.

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

  • ★★★★★
    Wonderful trip, they made it so easy to enjoy ourselves, crew was inviting and welcoming. will definitely be booking again

    Heather W. | November 27, 2025

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    We took our team out with Hunter for a combo lobstering and deep sea trip and he didn't let us down! First and foremost, Hunter is an ex-marine who is incredibly on top of his equipment, his boat, and his safety and was very clear about expectations for the day and what we should be doing at any point in time. After a quick scuba diving refresher & safety brief we put on our gear for a dive and were rewarded with a number of keeper lobsters, a bigger number of lobsters that were too small to keep, a lionfish which we speared, and too many great wildlife sightings to count including a big loggerhead turtle, a black grouper, and a nurse shark hoping for a handout. After the dive we put our gear away we drove a few miles further out to catch some yellowtail snapper. We started slow, but pretty soon were reeling in a yellowtail almost every cast. We probably caught 20-25 within a few hours, as well as a small yellow jack, a parrotfish, and an undersized red grouper. Lastly, we decided to use the last hour of our trip to try to hook into a big black grouper using some of our yellowtail as bait. This was a bit of a "go big or go home" bet and unfortunately didn't pay off for us this time - I wish we'd had a bit more time to drift and I'm sure we would have hooked one. Overall can't speak highly enough of Hunter and the experience diving and fishing in the Keys. There is such a variety of things to do that even on a full day trip you will never feel bored and can always pivot to something else. We even chased a frigate bird and threw some bucktails in the middle of the day at some bait that was busting. You won't go wrong booking a trip with Hunter.

    Attison B. | November 5, 2025

    Trip: Full Day Offshore - 30' Seahunter

  • ★★★★★
    Awesome trip Captain Brad put us on the fish all day

    Sam R. | November 2, 2025

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    Captain Brad did a great job! Very good boat.

    Jeff M. | October 13, 2025

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    Outstanding

    Jodie R. | October 9, 2025

    Trip: Key West Offshore Action

Other Featured Cities

Didn't Find What You Were Looking For?

Our guides are Damn Good Guides, which means they’re vetted by our team of outdoor experts who know them on a first-name basis. We hand pick each and every one of them, and our network spans all across the US and beyond.

The proof is in the pudding, and we’re incredibly proud of our 4.9 / 5 average review score. Hit the button below to see more trip options:

See All Sailfish Trips in Stock Island