Damn Good Sailfish Fishing Charters In Big Pine Key

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

Choose a Date
4.93/5 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 Big Pine Key, Fl

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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Big Pine Key

Big Pine Offshore Fishing

100% (2)
25 ft 1 - 12 People From $1,150
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, Nearshore Fishing in Key West

Marquesas Key Fishing Adventure

100% (18)
33 ft 1 - 4 People From $1,600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Key West Fishing Experience

100% (4)
32 ft 1 - 8 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 Marathon

Deep Sea Combo (Swordfishing)

100% (9)
35 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

Top Types of Sailfish Trips in Big Pine 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.”

Jonathan and Attison   |   Co-founders   |   Austin, Texas

All Target Species in Big Pine 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 Big Pine Key, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Marathon Offshore - 30’ Boca Grande

100% (16)
30 ft 1 - 6 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Key West

Key West Sportfishing Adventure

100% (6)
34 ft 1 - 6 People From $1,050
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Dry Tortugas Multi-Day Trip

NEW
50 ft 1 - 12 People From $5,900
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
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, Nearshore Fishing in Marathon

Wreck Fishing

100% (3)
33 ft 1 - 12 People From $1,050
See All Sailfish Trips in Big Pine Key

Need a Place to Stay?

Everything to Know About Booking a Big Pine Key sailfish fishing charter

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

Our Damn Good Guides currently offer 71 sailfish trips in Big Pine Key, and the most popular trips in the area are Chase Giants From Big Pine Key guided by Felipe, Big Pine Offshore Fishing guided by Tom, and Marquesas Key Fishing Adventure guided by Anthony.

Our guides in Big Pine Key are rated a 4.93 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 Big Pine Key? Check out our beginner and family friendly sailfish guides in Big Pine Key.

What types of sailfish fishing charters are common in Big Pine Key?

Deep Sea fishing is the most popular type of fishing for sailfish in Big Pine Key as well as nearshore fishing, inshore fishing, and flats fishing.

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

How much do Big Pine Key sailfish fishing charters cost?

Prices for sailfish in Big Pine Key can range anywhere from about $1,100 to $3,200, but the average price for a half day trip for sailfish in Big Pine Key is $1,470. The average price for a full day trip for sailfish in Big Pine Key is $3,007.

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 Big Pine Key?

The most popular season for sailfish fishing in Big Pine Key is summer, and most anglers book their trips 10 days in advance.

Do I need a Big Pine Key fishing license for sailfish and what are the bag limits for sailfish in Big Pine Key?

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

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

What's biting in Big Pine Key?

View Sailfish Fishing Reports from our damn good guides.

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 Big Pine Key