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Damn Good Trolling Charters In Key West

Check real-time availability on Key West trolling fishing trips. Online booking | 4.9 / 5 stars | Guides from $868

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Recently Booked Trolling Charters Near Key West, Fl

Fishing in Key West

Flats, Inshore, Nearshore Fishing Charter in Key West

Edge Of The Map Trip

100% (6)
25 ft 1 - 4 People From $650
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Fishing in Key West

Deep Sea, Nearshore Fishing Charter in Key West

Key West Sportfish Trip

93% (14)
37 ft 1 - 6 People From $1,150
Damn Good
A Certified Damn Good Guide is someone who goes above and beyond to show you an incredible experience on your trip. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Key West

Deep Sea, Inshore, Nearshore Fishing Charter in Key West

Offshore Fishing,Reef & Wreck And Sunset

100% (11)
35 ft 1 - 6 People From $900
Fishing in Key West

Nearshore Fishing Charter in Key West

Key West Sportfishing Adventure

100% (1)
34 ft 1 - 6 People From $1,050
Fishing in Key West

Deep Sea, Nearshore Fishing Charter in Key West

Legendary Fishing In Key West

100% (7)
55 ft 1 - 6 People From $1,100
Fishing in Key West

Deep Sea, Inshore Fishing Charter in Key West

Laid Back Key West

100% (3)
33 ft 1 - 6 People From $900

Most Popular Types of Trolling Trips in Key West

Top Species for Trolling in Key West

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More Trolling Charters Near Key West, Fl

Damn Good
A Certified Damn Good Guide is someone who goes above and beyond to show you an incredible experience on your trip. 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 Mixed Bag Trip in Key West

Join Captain Brad on an exciting fishing adventure in Key West, Florida. Captain Brad is extremely friendly and courteous, and wants to help you reel in your personal best! On these 4, 6, and 8-hour adventures, Captain Brad will help you catch a variety of species, including Mahi Mahi / Dorado, Black Grouper, Goliath Grouper, Red Grouper, King Mackerel / Kingfish, Sailfish, Red Snapper (depending on the season), Yellowtail Snapper, and Wahoo. You’ll be fishing aboard Capt. Brad’s 43-foot sportfisher which is equipped with a large fishing cockpit, a functioning Tuna Tower, and an extra-large live well capacity. On this trip, Captain Brad emphasizes light tackle but is more than happy to accommodate for live bait slow trolling, reef & wreck, dead bait trolling, kite fishing, and blue water fly fishing. Captain Brad will provide Penn, Shimano, and Daiwa rods, reels, tackle, and lures. They will also provide live bait, drinks, fly fishing equipment, and fish cleaning/filleting at no extra cost. A first mate will be on board to help you at all times. Make sure you bring a hat, sunscreen, and some food/snacks for the day! The crew is excited to give you a great fishing trip – it doesn’t matter if you’ve fished a hundred times or whether this is your first time taking the family fishing – there’s something for everyone to enjoy! Read More

Deep Sea, Nearshore Fishing Charter in Key West

Key West Mixed Bag Trip

100% (6)
43 ft 1 - 6 People From $850
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A Certified Damn Good Guide is someone who goes above and beyond to show you an incredible experience on your trip. 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

Deep Sea, Inshore, Jetty, Nearshore Fishing Charter in Key West

Key West Offshore Or Inshore

100% (11)
27 ft 1 - 6 People From $700
Veteran Operated
This trip is managed / operated by a veteran of the US armed forces.
Fishing in Key West
Fishing in Key West
Fishing in Key West
trip description for Ultimate Action Fishing in Key West in Key West

Experience the "Ultimate Action Fishing" adventure with Captain Nick in the vibrant waters of Key West! This trip is perfect for those seeking a thrilling fishing experience, targeting a wide variety of prized game fish in both deep sea and nearshore environments. Captain Nick will guide you through a diverse range 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, and trolling. Your targets for the day will 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, and Yellowtail Snapper. You'll be fishing aboard a 33' Center Console boat, designed for the 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 Paul provides all the necessary fishing equipment, including rods, reels, tackle, and bait. Just bring your favorite snacks, drinks, sunscreen, and a hat for sun protection. Whether you're an experienced angler or a beginner, Captain Nick's expertise and passion for fishing will ensure you have an unforgettable adventure. Read More

Deep Sea, Nearshore Fishing Charter in Key West

Ultimate Action Fishing In Key West

100% (3)
33 ft 1 - 4 People From $1,000
Damn Good
A Certified Damn Good Guide is someone who goes above and beyond to show you an incredible experience on your trip. 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 Sportfishing Trip in Key West

Captain Mark will guide you on a thrilling adventure through the waters of Key West, Florida! You’ll be fishing aboard Captain Mark’s “Cowboy,” a 45 sportfisher is a spectacular boat equipped with two 1100 HP engines that will get you out to your destination quickly and seamlessly. This boat will answer all of your sport fishing goals and interests. She features a large deck and a recently restored, comfortable interior. This boat is also fully air-conditioned, boasts performance-grade tackle, and has a fighting chair on the deck. She can accommodate up to 6 adventurous anglers and has a GPS, fishfinder, live bait well, and ice box. On this 4, 6, 8, 10, or 12-hour trip, you’ll be targeting a wide variety of species, including Billfish, like White Marlin and Sailfish, Mahi Mahi, Mutton Snapper, and Amberjack. You might also catch a few sharks. Prepare yourself to feel the intense power of this apex predator as you reel it in. 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 in Key West

Key West Sportfishing Trip

93% (14)
45 ft 1 - 6 People From $1,200
Damn Good
A Certified Damn Good Guide is someone who goes above and beyond to show you an incredible experience on your trip. 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 Fishing Slam in Key West

Captain Mark will guide you on a thrilling adventure through the waters of Key West, Florida! You’ll be fishing aboard Captain Mark’s 36-foot sportfisher, which is equipped with two 750 HP engines that will get you out to your destination quickly and seamlessly. She can accommodate up to 6 adventurous anglers and has a GPS, fishfinder, live bait well, and ice box. On this 4, 6, 8, 10, or 12-hour trip, you’ll be targeting a wide variety of species, including Billfish, like White Marlin and Sailfish, Mahi Mahi, Mutton Snapper, and Amberjack. You might also catch a few sharks. Prepare yourself to feel the intense power of this apex predator as you reel it in. 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 in Key West

Key West Fishing Slam

93% (14)
36 ft 1 - 6 People From $1,050
Fishing in Key West
Fishing in Key West
Fishing in Key West
trip description for Morning 1/2 Day Fishing Charter in Key West

Wake up and go fishing! A 4-hour fishing trip is a great way to fish and explore the local waters surrounding Key West. Our half-day trips usually leave the dock around 7:30 a.m. and return around 11:30 a.m. However, this may change depending on the conditions, time of year, and customer preference. Captain John's mission is always to provide the best fishing experience possible with the conditions at hand. His vessel, a 28' center console (built by Latitude Tournament Boats), is a true "hybrid" fishing machine. This means that on a nice day, you can comfortably fish offshore reefs, wrecks, and Gulfstream currents. You also have the option to fish backcountry channels, inshore wrecks, and nearshore patch reefs if the wind picks up. On a full day, we might have the opportunity to target multiple species both in the deep and the shallow. Captain John specializes in light tackle fishing. This means he'll match the rod and reel outfit to the size fish you're targeting to make for the best overall angling experience. If you would like to fly fish, the captain can accommodate you. However, you must bring your own fly fishing equipment. Expect to target Amberjack, Barracuda, Tuna, Wahoo, Mahi Mahi, Grouper, and more, depending on the length of your trip. Evening Tarpon trips are also offered. Live bait makes a big difference. Pilchards, pinfish, herring, ballyhoo, and blue crabs are some of the varieties you are likely to find in the livewell. Catching bait is part of the charter, and while it may take some extra time, your captain knows it makes the difference between a fantastic fishing trip and one that's just okay. Your fishing license is included. Bring sunblock (non-spray), sunglasses, a hat, snacks, and drinks. Book your trip and hit the water with Captain John! Read More

Deep Sea, Inshore, Nearshore Fishing Charter in Key West

Morning 1/2 Day Fishing Charter

83% (6)
25 ft 1 - 4 People From $800
See All Trolling Trips in Key West

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Everything to Know About Booking a Key West trolling charter

What are the best trolling charters in Key West?

Why should I book a trolling charter in Key West with Captain Experiences?

Our Damn Good Guides currently offer 54 trolling trips in Key West, and the most popular trips in the area are Edge of the Map Trip guided by Spencer, Key West Sportfish Trip guided by Mark, and Offshore Fishing,Reef & Wreck and Sunset guided by Antonio.

Our guides in Key West are rated a 4.9 out of 5 based on 3305 verified reviews on Captain Experiences.

All guides on Captain Experiences are licensed, insured, and 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 trolling guides / fishing lessons in Key West? Check out our beginner and family friendly trolling guides in Key West.

What types of trolling charters are common in Key West?

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

The most commonly sought after species for trolling in Key West are: 1. mahi mahi, 2. mutton snapper, 3. blackfin tuna, 4. yellowtail snapper, and 5. wahoo.

How much do Key West trolling fishing charters cost?

Prices for trolling in Key West can range anywhere from about $868 to $2,200, but the average price for a half day trip for trolling in Key West is $1,056. The average price for a full day trip for trolling in Key West is $1,659.

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 on a trolling charter in Key West?

The most popular season to go on a trolling charter in Key West is summer, and most anglers book their trips 31 days in advance.

Do I need a Key West fishing license and what are the bag limits in Key West?

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

Recent Reviews of Captain Experiences

  • ★★★★★
    We took a 10 hour charter with Mark and Chris and it was an excellent time. They made sure that both of our boys got to catch a shark and they each got several Mahi. I would definitely recommend them!

    Tammy G. with Mark B. of Key West, Florida

  • ★★★★★
    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. with Antonio E. of Key West, Florida

  • ★★★★★
    Had a great time out in the water!

    Salvador G. with Antonio E. of Key West, Florida

  • ★★★★★
    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. with Anthony D. of Key West, Florida

  • ★★★★★
    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. with Mike W. of Stock Island, Florida

  • ★★★★★
    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. with Hunter L. of Key West, Florida

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

    Houston H. with Antonio E. of Key West, Florida

  • ★★★★★
    He put us on the Best Fishing Day of our Life's... Hi and his Dad And His Son TONY #15. He was so Great and the day was Perfect 🥰. Now my whole family has caught a Mahi or Rainbow 🌈 Runner .

    Hugh H. with Antonio E. of Key West, Florida

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

    David R. with Thomas D. of Key West, Florida

  • ★★★★★
    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. with Thomas D. of Key West, Florida

  • ★★★★★
    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. with John D. of Key West, Florida

  • ★★★★★
    Tony and his Son Tony #15 Kicked Ass we caught Mahi 🤪 12. And a. 🌈 RAINBOW RUNNER 🏃‍♂️..MY daughter ate it on our way back to pur Room.. They are Family professionals. I would recommend you to call Tony direct he Rocks.. Best Fishing experience ever and they Fileted my fish and bagged them up 5 big bags full of about 500 dollars 💸 worth of fish.. I highly recommend them the are the 💣 bomb!!!

    Hugh H. with Antonio E. of Key West, Florida

  • ★★★★★
    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. with Mike W. of Stock Island, Florida

  • ★★★★★
    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. with Mark B. of Key West, Florida

  • ★★★★★
    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. with Brad S. of Key West, Florida

  • ★★★★★
    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. with John D. of Key West, Florida

  • ★★★★★
    Awesome experience. Captain chuck and Joe Joe were great. Nice boat, good times

    Stephen M. with Chuck T. of Key West, Florida

  • ★★★★★
    They nailed it with name! It was truly a Captain Experience and we had the pleasure of going out with Capt Hunter and his mate, Robert. The seas were rough, the sign was shining and the water was splashing. For most, they would have turned tail to head back to shore but the salt air was filled with the giggles of my family as Capt skirted over the waves, flawlessly. We bummed, we bounced, we laughed and we caught some beautiful fish. Capt Hunter was truly the perfect definition of an experienced Captain. He was safe, cautious, full of knowledge and fun! The whole 8 hour trip was worth every penny saved and every memory made. The Colonel (aka the Capt) will 💯 be our go to charter Capt for future trip. Robert, was fun and charming and a very valuable part of the crew. We truly had the best time and would highly recommend them to anyone. The Captain Experiences team goes above and beyond to make sure it’s smooth sailing from the moment you book a charter with them. The communication is second to none with them. Available at all times of the day. Thank you, Gentlemen for a exhilarating experience. You haven’t seen the last of us.

    Chandra B. with Hunter L. of Key West, Florida

  • ★★★★★
    Captain Mike and his crew were amazing!! We went out with 5 kids all under the age of 16 and they all caught fish and had a blast!! Blind Squirrel Rocks!!

    Fred S. with Mike W. of Stock Island, Florida

  • ★★★★★
    Had a fantastic day! Very relaxing and caught los of fish on the Cowgirl. The mate recommended the boathouse to take some of our catch for the restaurant to cook…Wow it was cooked to perfection!!

    Gene P. with Mark B. of Key West, Florida

How are fishing conditions in Key West?

View Key West Fishing Reports from our damn good guides.

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