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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

Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Big Pine Key

Deep Sea Fishing Charter in Big Pine Key

Chase Giants From Big Pine Key

NEW
33 ft 1 - 6 People From $1,150
Fishing in Naval Air Station Key West

Deep Sea Fishing Charter near Big Pine Key

Key West Sportfishing Adventure!

100% (3)
42 ft 1 - 6 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 Key West

Deep Sea Fishing Charter near Big Pine Key

Dawn To Dusk Key West Fishing Trip

100% (8)
43 ft 1 - 6 People From $2,000
Fishing in Marathon

Deep Sea Fishing Charter near Big Pine Key

Marathon Offshore - 30’ Boca Grande

100% (13)
30 ft 1 - 6 People From $1,000
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Marathon

Deep Sea Fishing Charter near Big Pine Key

Offshore Trolling And Bottom Fishing

100% (2)
38 ft 1 - 6 People From $1,400
Fishing in Key West

Deep Sea Fishing Charter near Big Pine Key

Key West Big Game Fishing

NEW
34 ft 1 - 6 People From $1,500

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

Target Species in Big Pine Key

January February March April May June July August September October November December
Almaco Jack
Not Ideal
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Amberjack
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Barracuda
Not Ideal
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Blackfin Tuna
Not Ideal
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Good
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Bluefin Tuna
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Good
Not Ideal
Bonefish
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Bull Shark
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Good
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Cero Mackerel
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Good
Not Ideal
Gag Grouper
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Good
Not Ideal
Jack Crevalle
Not Ideal
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Good
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Kingfish
Not Ideal
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Good
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Good
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Lane Snapper
Not Ideal
Not Ideal
Good
Good
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Good
Not Ideal
Mahi Mahi
Not Ideal
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Good
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Mangrove Snapper
Not Ideal
Not Ideal
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Good
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Mutton Snapper
Not Ideal
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Good
Not Ideal
Permit
Not Ideal
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Good
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Red Grouper
Not Ideal
Not Ideal
Good
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Good
Not Ideal
Redfish
Not Ideal
Not Ideal
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Good
Not Ideal
Snook
Not Ideal
Not Ideal
Good
Good
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Good
Not Ideal
Spanish Mackerel
Not Ideal
Not Ideal
Good
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Good
Not Ideal
Speckled Trout
Not Ideal
Not Ideal
Good
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Good
Not Ideal
Strawberry Grouper
Not Ideal
Not Ideal
Good
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Good
Not Ideal
Tarpon
Not Ideal
Not Ideal
Good
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Good
Not Ideal
Wahoo
Not Ideal
Not Ideal
Good
Good
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Good
Not Ideal
Yellowtail Amberjack
Not Ideal
Not Ideal
Good
Good
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Good
Not Ideal
Yellowtail Snapper
Not Ideal
Not Ideal
Good
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Not Ideal
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  • 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 Marathon
Fishing in Marathon
Fishing in Marathon
trip description for Marathon Offshore Slam- 50’ Bertram in Marathon

Join Captain Joel on his 50' Bertram sportfisher for an exciting offshore fishing charter out of Marathon, FL! n this epic trip, you'll be targeting some of the most prized gamefish in the area, including Blackfin Tuna, Mahi Mahi, and Wahoo! As you board the boat, you'll be greeted by Captain Joel and his experienced crew, who will provide you with a safety briefing and a rundown of the day's itinerary. Once everyone is ready, you'll set off from the dock and head out into the crystal-clear waters of the Florida Keys. As you make your way out to the fishing grounds, Captain Joel will share his knowledge of the area and give you some tips and techniques to maximize your chances of landing a big catch. You'll be fishing with top-of-the-line equipment, including high-quality reels and rods, and all bait and tackle will be provided. Once you arrive at the fishing grounds, the excitement will begin! Blackfin Tuna, Mahi Mahi, and Wahoo are all known for their fast and furious fighting style, and you'll need to be quick and agile to reel them in. With Captain Joel's expert guidance, you'll have the best chance of landing the catch of a lifetime. Throughout the day, you'll have the opportunity to relax and enjoy the beautiful scenery of the Florida Keys, soak up some sun, and spend some quality time with your fishing buddies! And, of course, you'll have plenty of opportunities to snap some photos of your impressive catches to share with your friends and family. At the end of the charter, Captain Joel and his crew will clean and fillet your fish, so you can take your catch home and enjoy it for dinner. Whether you're a seasoned angler or a first-time fisherman, this offshore fishing charter with Captain Joel is sure to be an unforgettable experience. Read More

Deep Sea, Inshore Fishing Charter near Big Pine Key

Marathon Offshore Slam- 50’ Bertram

100% (13)
50 ft 1 - 6 People From $1,895
Fishing in Key West
Fishing in Key West
Fishing in Key West
trip description for Reefs, Bays, or Backcountry in Key West

This fishing adventure with Captain Spencer out of Key West provides you with endless opportunities! Whether it's fishing the backcountry of the Gulf of Mexico, chasing fish in Key West Harbor, or fishing the reefs on the Atlantic side, Captain Spencer is ready to do it all. Captain Spencer prides himself on customizing his trips to his client's goals so let him know what your ideal day looks like in the days leading up to the trip and he will plan it out! The beauty of the Florida Keys, and especially Key West, is that there is such a variety of fish to catch. You can explore the backcountry for Redfish, Snook, Bonefish, and Mangrove Snapper; anchor-up on a channel in Key West Harbor to target Sharks, Cudas, Jacks, and Tarpon; or hit it out to the reefs for a myriad of grouper and snapper species, permit and even target Sails under the right conditions! Captain Spencers 25' Pathfinder is extremely versatile in this regard shallow enough to maneuver the backcountry and local grass flats, and sturdy enough to handle the light chop of the open ocean. This vessel can accommodate 6 guests, however, Captain Spencer prefers to fish with 4 or less. Captain Spencer can also make accommodations to pick you up from many places around Key West. If you are staying somewhere with water access let us know and Captain Spencer will try to accommodate picking you up from your location. Read More

Flats, Nearshore Fishing Charter near Big Pine Key

Reefs, Bays, Or Backcountry

100% (6)
25 ft 1 - 4 People From $850
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 Key West
Fishing in Key West
Fishing in Key West
trip description for Key West Sportfish Trip in Key West

Captain Mark will guide you on an action-packed adventure through the waters of Key West, Florida! You’ll be fishing aboard Captain Mark’s 37-foot Contender side console powered by two 250 HP Yamaha engines. She comes with outriggers, downriggers, and a live bait well. She also boasts air conditioning, a multimedia system, TV, refrigerator, and an ice-box. On this trip, you’ll be targeting a wide variety of species, including Black Grouper, Blackfin Tuna, Blue Marlin, Dorado (Mahi Mahi), Yellowtail, Wahoo, and many more. The longer you go, the farther out you can travel, and the farther out you travel, the bigger the fish get! Don’t forget to bring a cooler to take home your day’s catch, food and drinks for the day (no glass), sunscreen, and a hat. Captain Mark will provide all rods, reels, tackle, and fishing licenses. Let go of your daily responsibilities and have some fun fishing with Captain Mark! Read More

Deep Sea, Nearshore Fishing Charter near Big Pine Key

Key West Sportfish Trip

94% (18)
37 ft 1 - 6 People From $1,150
Fishing in Key West
Fishing in Key West
Fishing in Key West
trip description for Key West Offshore Action in Key West

Climb aboard with Captain John and experience an action-packed day of fishing in Key West, Florida. If you have never been to Key West before, you’re missing out! And if you’re looking for a knowledgeable charter captain to take you out, Captain John is a great choice. As a 5th generation fisherman in Key West, Captain John knows exactly where the fish bite. Test your casting accuracy as you target Amberjack, Cobia, Goliath Grouper, African Pompano, Sailfish, Bull SharkYellowtail Snapper, Swordfish, Blackfin Tuna, and many more species. You’ll be fishing aboard Captain John’s 33-foot center console equipped with two 300 HP engines. She also has a GPS, fishfinder, flybridge, live bait well, outriggers, and tuna tubes. Captain John will provide Spearfishing Equipment and Snorkeling equipment free of charge if you’re interested. He welcomes 6 anglers on these 4, 6, and 8-hour adventures. Make sure you bring food and drinks for the day (preferably no glass) as well as a hat and sunscreen. Captain John will provide all licenses, rods, reels, lures, and tackle. He will also prepare live bait before the trip, although you can catch the bait during the trip if you’d like. For the 6-and 8-hour trips, a first mate will be on board to help you at all times. They will help you clean and fillet your fish at the end of the trip. Whatever your skill level, there is a fish out here with your name on it. Come and join Captain John for an exciting day of fishing! Read More

Deep Sea Fishing Charter near Big Pine Key

Key West Offshore Action

88% (8)
33 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 Key West
Fishing in Key West
Fishing in Key West
trip description for Private Half Day Charter in Key West

4 hours on the beautiful waters of the Atlantic Ocean or the Gulf of Mexico. We can fish for a variety of species based on the time of year and what is in season. We start the day catching live bait, depending on what we are planning to fish for it can be anything from casting for Pinfish, Thread Fins, Ballyhoo Etc to throwing the cast net for some Pilchards, Mojarra or Mahua. You can keep your edible catch or simply catch and release. We can talk and customize your trip based on your preferences. Read More

Deep Sea, Inshore Fishing Charter near Big Pine Key

Private Half Day Charter

100% (2)
28 ft 1 - 4 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 Key West
Fishing in Key West
Fishing in Key West
trip description for Ultimate Action Fishing in Key West in Key West

Embark on the "Ultimate Action Fishing" adventure with Captain Anthony in the vibrant waters of Key West! This trip is ideal for thrill-seekers and fishing enthusiasts looking to target a wide variety of prized game fish in both deep sea and nearshore environments. Under Captain Anthony's expert guidance, you'll explore an array of fishing techniques, including: - Artificial lure fishing - Bottom fishing - Cut bait fishing - Deep dropping - Drift fishing - Heavy tackle fishing - Jigging - Kite fishing - Light tackle fishing - Live bait fishing - Trolling Your targets for the day include an impressive list of species such as: - African Pompano - Amberjack - Barracuda - Blackfin Tuna - Blue Marlin - Cobia - Gag Grouper - Goliath Grouper - Lane Snapper - Lemon Shark - Mahi Mahi - Mangrove Snapper - Mutton Snapper - Red Grouper - Sailfish - Snowy Grouper - Tarpon - Tilefish - Wahoo - Yellowtail Snapper You'll be fishing aboard a 33' Center Console boat, specifically designed for ultimate fishing action. This vessel is fully equipped with top-of-the-line fishing gear and amenities, ensuring a comfortable and productive day on the water. With its spacious deck and powerful engines, the boat is perfect for navigating both deep sea and nearshore waters. Captain Anthony provides all the necessary fishing equipment, including rods, reels, tackle, and bait. All you need to bring are your favorite snacks, drinks, sunscreen, and a hat for sun protection. Whether you're an experienced angler or a beginner, Captain Anthony's expertise and passion for fishing will ensure you have an unforgettable adventure. His personalized approach and extensive knowledge of the local waters will make your fishing trip an exciting and memorable experience. Join Captain Anthony for the ultimate fishing adventure in Key West, where thrilling catches and breathtaking scenery await! Read More

Deep Sea, Inshore, Jetty, Nearshore Fishing Charter near Big Pine Key

Ultimate Action Fishing In Key West

100% (3)
33 ft 1 - 6 People From $800
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

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 58 sailfish trip in Big Pine Key: Chase Giants from Big Pine Key guided by Felipe.

Our guides in Big Pine Key are rated a 4.91 out of 5 based on 3535 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 jetty fishing.

The most common fishing techniques in Big Pine Key are trolling, bottom fishing, and light tackle fishing but heavy 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 $940 to $2,400, but the average price for a half day trip for sailfish in Big Pine Key is $1,134. The average price for a full day trip for sailfish in Big Pine Key is $1,720.

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 9 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

  • ★★★★★
    Excellent guide and first mate. Both were great. Stayed over our time to be sure all the kids caught something. Highly recommend!!!

    Graham S. | September 16, 2024

    Trip: Key West Fishing Slam

  • ★★★★★
    Chris & Will were great. Knowledgeable, professional, engaging and put us on the fish. Would highly recommend this charter.

    Doug B. | September 11, 2024

    Trip: Key West Sportfish Trip

  • ★★★★★
    We had an amazing time! We had a special interest in Mahi and captain brad and his first mate made it happen. It was great, they made us feel super comfortable and confident. We were able to score Mackerel, Yellowtail and we latched on 3 Mahi’s at the very very last second! Super lucky. Brad and his first mate made it happen! We were able to leave with 2 mackerels and 2 Mahi Mahi’s! Thank you! You won’t regret booking with them. Special experience.

    María A. | September 2, 2024

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    My families trip with Captain John was awesome. John is a humble, hardworking, easy going, chill, dude and fit right in with our families vibe. He was great with our 5 year old son and answered all of his many fishing questions. John made it clear that between the time of year and conditions that day we would have to really work at it to get anything. That’s exactly what we did and we ended up catching a good amount of fish. Most importantly our 5 year old son, who is obsessed with fishing, had the time of his life and caught fish he’s never seen before. 5 stars, highly recommend. If you have a small group this is the charter to go on!

    Jacob D. | August 25, 2024

    Trip: Full Day Private Fishing Charter

  • ★★★★★
    Captain Brad and his first mate were amazing. It was my first time fishing off of a boat and I'm glad it was with them! They were both very patient, helpful, and made it an unforgettable experience. We caught snapper and grouper and even hooked an eel! Thanks to both of you for a fantastic time on the water. Highly recommend

    Karen E. | August 19, 2024

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    Steve and woody were absolutely a load of fun although the fish were not biting they continued to try !! Very enjoyable time !

    Marcie R. | August 17, 2024

    Trip: Key West Fishing Slam

  • ★★★★★
    Great day on the water, Captain Mark and mate Will were awesome. They put me on fish and stayed out until the last minute. I would definitely recommend.

    Nicholas W. | August 8, 2024

    Trip: Key West Deep Sea Run - 40' Luhrs

  • ★★★★★
    Our charter with Captain John was incredible! He was very professional but also personable! We enjoyed everything about the fishing trip! We had a beautiful day & caught several large dolphins! Will definitely rebook with Capt. John the next time we are in Key West!

    Deanna H. | July 31, 2024

    Trip: Morning 1/2 Day Fishing Charter

  • ★★★★★
    Guys were awesome !! They were all ready to go when I got to the boat Tony and Tony Sr absolute gentlemen and worked very hard and got me mahi, tuna, and barracudas definitely go out with again

    Paul M. | July 22, 2024

    Trip: Key West Offshore or Inshore

  • ★★★★★
    We had a great time with Josh! Josh was very knowledgeable about the waters that made for a successful fishing trip! Thanks for everything!!

    Jacque D. | July 20, 2024

    Trip: Offshore Trolling and Bottom Fishing

  • ★★★★★
    We had an absolutely amazing time deep sea fishing with Captain Anthony! He is a fun and knowledgeable fisherman with LOTS of experience and great stories (ask him about how he’d dive for lobsters to impress his dates). He does all the work but lets you learn and participate as much or as little as you want. We knew we had an expert when we heard the radio chatter of all the other guides complaining that nothing was biting, while we pulled in six (only four mahi in pic). The other two were a small tuna and a ~32” barracuda). We highly recommend Kilo Whiskey Charter & Captain Anthony!

    Dan W. | July 18, 2024

    Trip: Ultimate Action Fishing in Key West

  • ★★★★★
    Absolutely the highlight of our trip. Mike and his crew were fantastic teachers, patient and focused on helping all of us catch terrific fish. They are great with kids of all ages - 5 years to 16 years. Everyone had a great time and we caught a lot of fish.

    Vicki L. | July 16, 2024

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    Was a great trip, got on some nice fish. Got surprised by a large school of smaller mahi mahi but had fun with the instant hook up and seemed to last a good bit. Captain was great, very knowledgeable and supplied drinks if we needed any. The boat was clean and spacious for the both of us and had plenty of rods in the water.

    Tony P. | July 12, 2024

    Trip: Full Day Offshore - 30' Seahunter

  • ★★★★★
    Captain Tony was great. We'd definitely book again.

    Houston H. | July 9, 2024

    Trip: Key West Offshore or Inshore

  • ★★★★★
    Fantastic trip with Capt. Joel and Darren. Got us on some great Mahi Mahi, and kept at it for the whole trip. Highly recommended.

    David L. | July 8, 2024

    Trip: Marathon Offshore - 30’ Grady White

  • ★★★★★
    Had a great time Captain Steve and First mate Jeff was very professional.

    David R. | July 5, 2024

    Trip: Key West Deep Sea Fishing (Private)

  • ★★★★★
    Great Captain, great Mate, great boat and great time! Captain Steve got us on the Mahi and slayed em! Full limit on Mahi and a couple of barracuda. We had one sailfish come look but not for lack of trying! Jeff knows his stuff and never stopped working and made sure we were fishing the entire time. We completed our limit by landing all three of a triple set. I have fished my whole life and this was a fantastic trip. Highly recommend the Sea-clusion and Captain Steve.

    Arik G. | July 5, 2024

    Trip: Key West Deep Sea Fishing (Private)

  • ★★★★★
    Capt John was top notch!! Our planned morning trip hit a snag due to bad weather…But John was honest and informative suggesting that we should hold off a few hours…so we did. Our afternoon ended up being an awesome fishing encounter. We would highly recommend…thank you Capt John!!!

    Kelly L. | July 1, 2024

    Trip: Morning 1/2 Day Fishing Charter

  • ★★★★★
    My wife and I did a mix of reef fishing and offshore fishing to make an 8 hour trip. The bite was spotty at times, but we found a few schools of mahi mahi and were able to catch several of them throughout the day! We only had one keeper size, but it was very exciting to get into them and watch them hit our baits. Captain Steve and first mate Mike worked nonstop to get us into more fish. They can’t control if the fish will bite, but they certainly gave it their best effort. They also had great hospitality and offered plenty of fun stories and advice. We took our fresh catch to Lazy Days that evening and had an incredible dinner.

    Cooper S. | June 27, 2024

    Trip: Marathon Key Nearshore Run

  • ★★★★★
    The family had an absolutely phenomenal time with Captain Mike and his crew. We caught plenty of fish. The crew was very helpful to the family. The boat was great. I will 100% recommend them to anyone looking for a great trip.

    Tommy L. | June 25, 2024

    Trip: Key West Nearshore/Offshore Trip

What's biting in Big Pine Key?

View Sailfish Fishing Reports from our damn good guides.

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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