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
4.89/5 Average Rating

Damn Good Guides

Experts Available 24/7

100% Weather Guarantee

Recently Booked Sailfish Fishing Charters In Big Pine Key

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Key West

Southernmost Mahi Offshore Fishing

100% (3) Guided by Garrett
29 ft 1 - 6 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter in Stock Island

Key West Nearshore/Offshore Trip

100% (6) Guided by Mike
63 ft 1 - 12 People From $1,850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Key West

Key West Offshore Action

89% (9) Guided by John
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 Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore Fishing Charter in Key West

Key West Deep Sea Run - 40' Luhrs

94% (18) Managed by Mark
40 ft 1 - 6 People From $1,400
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, Nearshore Fishing Charter in Key West

Key West Mixed Bag Trip

100% (8) Guided by Brad
43 ft 1 - 6 People From $950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore Fishing Charter in Key West

Afternoon 1/2 Day Fishing

88% (8) Guided by John
25 ft 1 - 4 People From $800
View All

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

More Sailfish Fishing Charters In Big Pine Key

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter in Key West

Legendary Fishing In Key West

100% (8) Guided by Chuck
55 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, Nearshore Fishing Charter in Key West

Key West Sportfish Trip

94% (18) Managed by Mark
37 ft 1 - 6 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 Charter in Key West

Full Day Offshore - 30' Seahunter

100% (18) Guided by Hunter
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, Nearshore Fishing Charter in Key West

Key West Fishing Slam

94% (18) Managed by Mark
36 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 Charter in Key West

Dawn To Dusk Key West Fishing Trip

100% (8) Guided by Brad
43 ft 1 - 6 People From $2,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Marathon

Marathon Key Nearshore Run

100% (8) Managed by Steve
31 ft 1 - 6 People From $900
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?

The best sailfish fishing charters in Big Pine Key are:

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

Our Damn Good Guides currently offer 30 sailfish trips in Big Pine Key, and the most popular trips in the area are Southernmost Mahi Offshore Fishing guided by Garrett, Key West Offshore Action guided by John, and Key West Nearshore/Offshore Trip guided by Mike.

Our guides in Big Pine Key are rated a 4.89 out of 5 based on 3716 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 light tackle fishing, trolling, and heavy tackle fishing but bottom 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 $1,030 to $2,617, but the average price for a half day trip for sailfish in Big Pine Key is $1,309. The average price for a full day trip for sailfish in Big Pine Key is $1,858.

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 21 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 sailfish fishing licenses in Big Pine Key, sailfish bag limits, and fishing season regulations for sailfish in Big Pine Key. When in doubt, your fishing guide will always know the right sailfish rules and regulations in Big Pine Key.

Recent Reviews

  • ★★★★★
    We had a blast with Joe and Captain Chuck. Will definitely return!

    Yohannes H. | October 28, 2024

    Trip: Legendary Fishing in Key West

  • ★★★★★
    We had such a great time and our guide was fun, knowledgeable, and put us on the fish all trip! We will be going back for sure.

    Rae S. | October 6, 2024

    Trip: Key West Offshore Action

  • ★★★★★
    Captain Steve and mate Stan are the best they put us on the fish and we will definitely be back

    Jason R. | September 25, 2024

    Trip: Key West Sportfishing Adventure

  • ★★★★★
    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

  • ★★★★★
    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

  • ★★★★★
    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

  • ★★★★★
    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

  • ★★★★★
    My son, friend and i went out on Cowboy II with Captain Mark and Best Mate Ever Anthony. The Captain has eagle eyes and Anthony moves like an octopus, neither would give up until we CRUSHED IT. 2 Black Tail Tuna and 9 Mahi later we were happy as fishing guys could be. I am happy to recommend them for your trip with the guys. Enjoy Paul Cella

    Paul C. | June 24, 2024

    Trip: Key West Fishing Slam

  • ★★★★★
    Captain Brad and his deck hand Dennis was awesome given the weather and seas where not very good they still put us on fish and took care of us perfectly. Boat was very nice clean had lots of room (perfect set up) . Would highly recommended Captain Brad !!!!

    Johnny E. | June 23, 2024

    Trip: Key West Mixed Bag Trip

  • ★★★★★
    We had a great time on our first family fishing trip. We brought enthusiasm, and very little experience. John was a great teacher for all of us, and took us to several good spots in Lake Passage. We caught shark, black grouper and enough snapper to feast on for days. The fine folks at Hurricane Hole cooked it up for us and it was amazing!! We would definitely book another trip with John!!

    Karl H. | June 23, 2024

    Trip: Morning 1/2 Day Fishing Charter

Other Fishing Species in Big Pine Key

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 Big Pine Key