Damn Good Deep Dropping Charters In The Florida Keys

Check real-time availability and compare rates on Florida Keys deep dropping fishing trips. Confidently book your next day on the water.

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Recently Booked Deep Dropping Charters In The Florida Keys

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Key Largo

Key Largo Reef And Offshore

100% (1)
34 ft 1 - 5 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Key West

Key West Offshore Action

89% (9)
33 ft 1 - 6 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Key Largo

Swordfish Slam

100% (3)
35 ft 1 - 6 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter in Key West

Legendary Fishing In Key West

100% (8)
55 ft 1 - 6 People From $1,100
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore Fishing Charter in Key Largo

Key Largo Reef Trip

100% (1)
25 ft 1 - 3 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter in Key Largo

Keys All-Day Adventure!

NEW
48 ft 1 - 6 People From $2,100

Top Types of Deep Dropping Trips in the Florida Keys

Top Species for Deep Dropping in the Florida Keys

“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 Deep Dropping Charters In The Florida Keys

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Duck Key

Keys Fishing Adventure

100% (1)
36 ft 1 - 6 People From $1,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter in Key West

Key West Fishing Experience

100% (2)
32 ft 1 - 8 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing Charter in Little Torch Key

Reef Fishing

100% (9)
27 ft 1 - 6 People From $700
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 Marathon

Mahi / Offshore Combo

100% (2)
35 ft 1 - 6 People From $1,600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Key West

Key West Big Game Fishing

NEW
34 ft 1 - 6 People From $1,500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing Charter in Key West

Long-Range Key West Trip

89% (9)
33 ft 1 - 6 People From $1,350
See All Deep Dropping Trips in the Florida Keys

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Everything to Know About Booking a Florida Keys deep dropping charter

What are the best deep dropping charters in the Florida Keys?

Why should I book a deep dropping charter in the Florida Keys with Captain Experiences?

Our Damn Good Guides currently offer 21 deep dropping trips in the Florida Keys, and the most popular trips in the area are Key Largo Reef and Offshore guided by Jim, Key West Offshore Action guided by John, and Swordfish Slam guided by Eric.

Our guides in the Florida Keys are rated a 4.85 out of 5 based on 3710 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 deep dropping guides / fishing lessons in the Florida Keys? Check out our beginner and family friendly deep dropping guides in the Florida Keys.

What types of deep dropping charters are common in the Florida Keys?

Deep Sea fishing is the most popular type of fishing for deep dropping in the Florida Keys as well as nearshore fishing and inshore fishing.

The most commonly sought after species for deep dropping in the Florida Keys are: 1. blackfin tuna, 2. sailfish, 3. mahi mahi, 4. yellowtail snapper, and 5. mutton snapper.

How much do Florida Keys deep dropping fishing charters cost?

Prices for deep dropping in the Florida Keys can range anywhere from about $900 to $2,385, but the average price for a half day trip for deep dropping in the Florida Keys is $1,215. The average price for a full day trip for deep dropping in the Florida Keys is $1,753.

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 deep dropping charter in the Florida Keys?

The most popular season to go on a deep dropping charter in the Florida Keys is spring, and most anglers book their trips 7 days in advance.

Do I need a the Florida Keys fishing license and what are the bag limits in the Florida Keys?

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

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

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

    Stephen M. | June 22, 2024

    Trip: Legendary Fishing in Key West

  • ★★★★★
    Great Trip. Would schedule another.

    David T. | May 9, 2024

    Trip: Reef Fishing

  • ★★★★★
    Had a great time today Caught a lot of fish. Thoroughly enjoyed our charter. Will return.

    Jorge E. | May 9, 2024

    Trip: Legendary Fishing in Key West

  • ★★★★★
    The best charter captain we have found and we have been on charters all over Fl.

    Theresa L. | May 5, 2024

    Trip: Reef Fishing

  • ★★★★★
    Captain Allen was absolutely amazing! We have 3 children and he was so awesome with them and very accommodating! He took us out and showed us a wonderful time and we came back with a ton of fish!

    Sarah L. | April 25, 2024

    Trip: Reef Fishing

  • ★★★★★
    Had a fantastic trip with Captain John in July of 2023. Went for a morning trip on our honeymoon, caught tons of fish, had a lot of fun. John and his first mate were very competent, personable, and provided an excellent experience. The boat was well outfitted, John knew several spots with lots of fish, and gave us more time than we'd paid for. Great experience, will absolutely book again next time we're in the keys.

    Clare D. | March 24, 2024

    Trip: Key West Offshore Action

  • ★★★★★
    Excellent trip with John. Good guys, on fish all day and had a great time. Definitely would book again!

    Kevin V. | March 16, 2024

    Trip: Key West Offshore Action

  • ★★★★★
    Great fishing trip, memorable experience, would refer John and partner to anyone interested charting fishing trip in KeyWest!

    Rob R. | March 15, 2024

    Trip: Key West Offshore Action

  • ★★★★★
    Great time! Very nice guy, helpful, knowledgeable and friendly. Would definitely go out again.

    Jeff C. | March 12, 2024

    Trip: Key Largo Reef Trip

  • ★★★★★
    Did not love the trip. We would ask questions and get one word answers. Lots of smoking, and some chewing of tobacco. not enjoyable.

    Linda F. | February 4, 2024

    Trip: Legendary Fishing in Key West

  • ★★★★★
    Eric was the best! Very personable and fun. We will do this again.

    Teri H. | December 8, 2023

    Trip: Laid Back Key West

  • ★★★★★
    Fabulous fun and great experience with the crew!!!

    David H. | December 4, 2023

    Trip: Legendary Fishing in Key West

  • ★★★★★
    Nice boat even good in rough sea. Worked hard to find fish.

    Steve G. | November 14, 2023

    Trip: Laid Back Key West

  • ★★★★★
    Great crew, they worked very hard, but the fish just wasn’t there, we’ll book with them again

    Ted M. | October 13, 2023

    Trip: Legendary Fishing in Key West

  • ★★★★★
    Captain Jake was great! We caught out limit of Mahi and a great time.

    Gregory S. | August 20, 2023

    Trip: Key West Offshore Action

  • ★★★★★
    We had an amazing time with "Off the Charts" charter and Captain Joe was fantastic! He has a very easy going, friendly personality and it was easy to see he aims to please his customers. He was also extremely patient with my kids and seemed to enjoy teaching them some of his fishing techniques. While my boys have been fishing their whole lives, this was their first time trolling. They loved every minute, especially reeling in their fist Mahi Mahi! I was very satisfied and would highly recommend him for your fishing adventure. We may have just been another charter family for him, but he will live infinitely in our Key West vacation memories!

    Alexis C. | August 7, 2023

    Trip: Key West Fishing Experience

  • ★★★★★
    Great day on the water. We all caught fish. Joe was a great guide.

    Karen D. | July 14, 2023

    Trip: Legendary Fishing in Key West

  • ★★★★★
    Great experience! We had a blast fishing with the family. Steve was fun, polite & took the time to teach us! I also forgot my AirPods on the boat & he was nice enough to bring them to our hotel the next morning 🫶🏻 Thank you Steve!

    Jorge R. | June 10, 2023

    Trip: Key West Offshore Action

Other Fishing Techniques in the Florida Keys

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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 Deep Dropping Trips in the Florida Keys