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.

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Recently Booked Sailfish Fishing Charters In Big Pine 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 Fishing in Big Pine Key

Big Pine Offshore Fishing

100% (3)
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 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

Inshore, Deep Sea, Flats in Big Pine Key

4 Hr (pm)

100% (5)
27 ft 1 - 8 People From $900
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
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 Fishing in Marathon

Offshore Fishing

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

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 Key West

Offshore Fishing Trip

NEW
31 ft 1 - 6 People From $900
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 Fishing in Key West

Dry Tortugas Smash

96% (28)
32 ft 1 - 6 People From $2,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

10 Hour Trip – Offshore Extreme

100% (3)
28 ft 1 - 6 People From $1,950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Marathon

Wreck Fishing

100% (5)
33 ft 1 - 12 People From $1,050
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Full Day Offshore Extreme Fishing

100% (2)
35 ft 1 - 12 People From $1,800
See All Sailfish Trips in Big Pine Key

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

What are the best sailfish fishing charters in Big Pine Key?

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

Our Damn Good Guides currently offer 77 sailfish trips in Big Pine Key, and the most popular trips in the area are Big Pine Offshore Fishing guided by Tom, Chase Giants From Big Pine Key guided by Felipe, and 4 Hr (pm) guided by Chris.

Our guides in Big Pine Key are rated a 4.93 out of 5 based on 7167 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 inshore fishing and flats fishing.

The most common fishing techniques in Big Pine Key are artificial lure fishing, drift fishing, and trolling but bottom fishing and heavy tackle fishing 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 $1,150 to $3,600, but the average price for a half day trip for sailfish in Big Pine Key is $1,605. The average price for a full day trip for sailfish in Big Pine Key is $3,056.

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

  • ★★★★★
    I am caught some great fish. Mahi Mahi and a Wahoo! Great trip. Joel wasn’t able to join us but he had a buddy named Johnny assist us for the day. A bunch of dumb guys trying to catch fish. Johnny was very good at what he does. Just not good at directions! 10/10

    Zachary W. | May 11, 2026

    Trip: Private Offshore Fishing

  • ★★★★★
    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

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What's biting in Big Pine Key?

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See All Sailfish Trips in Big Pine Key