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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4.93/5 Average Rating

Recently Booked Deep Dropping Charters In The Florida Keys

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key Largo

Deep Sea, Wreck And Reef

100% (17)
34 ft 1 - 6 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key Largo

Swordfish Slam

100% (10)
35 ft 1 - 6 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key Largo

Offshore Fishing Key Largo

100% (4)
28 ft 1 - 4 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key Largo

Key Largo Reef And Offshore

100% (12)
34 ft 1 - 5 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 in Key Largo

8 Hours Of Fishing Excitement

100% (52)
24 ft 1 - 12 People From $1,200
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Tavernier

Florida Fishin' Frenzy

100% (5)
25 ft 1 - 4 People From $750

Top Types of Deep Dropping Trips in the Florida Keys

What makes Captain Experiences Damn Good?

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You will only find quality, vetted guides on Captain Experiences, and we know them all on a first-name basis.

Damn Good Guides

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Our US-based team is available 24/7 to help you with any questions or concerns.

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4.9 / 5 Average Rating

We hand pick our Damn Good Guides, and our network spans across North America and beyond.

4.9 / 5 Average Rating

“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

Top Species for Deep Dropping in the Florida Keys

More Deep Dropping Charters In The Florida Keys

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Keys Offshore Fishing Adventure

100% (36)
26 ft 1 - 4 People From $1,275
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 Islamorada

Extended Swordfish Trip

100% (21)
37 ft 1 - 6 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Islamorada

Afternoon Half

100% (23)
44 ft 1 - 12 People From $1,100
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Islamorada

6 Hour 3/4 Day

100% (2)
34 ft 1 - 12 People From $1,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Full Day Deep Sea

100% (10)
39 ft 1 - 12 People From $1,600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

3/4 Day Deep Sea

100% (10)
39 ft 1 - 12 People From $1,300

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:

Everything to Know About Booking a Florida Keys deep dropping charter

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

The best deep dropping charters in the Florida Keys are:

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

Our Damn Good Guides currently offer 67 deep dropping trips in the Florida Keys, and the most popular trips in the area are Deep Sea, Wreck And Reef guided by Dan, Swordfish Slam guided by Eric, and Offshore Fishing Key Largo guided by Justin.

Our guides in the Florida Keys are rated a 4.93 out of 5 based on 8854 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, inshore fishing, and jetty fishing.

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

How much do Florida Keys deep dropping fishing charters cost?

Prices for deep dropping in the Florida Keys can range anywhere from about $1,300 to $4,000, but the average price for a half day trip for deep dropping in the Florida Keys is $1,781. The average price for a full day trip for deep dropping in the Florida Keys is $3,219.

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 summer, and most anglers book their trips 34 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 guide will always know all the relevant rules and regulations in the Florida Keys.

Recent Reviews

  • ★★★★★
    Excellent day, excellent mate , captain got us in good fish

    Jason H. | August 6, 2026

    Trip: Key West 47 Ft Hatteras

  • ★★★★★
    We booked a trip on their 47’ Hatteras, and it did not disappoint. Captain Nels put us on consistent action all day long and you could tell right away he knew exactly where to look and wasn’t afraid to move around until we found them. First Mate Tyson kept things running smoothly the entire trip. The whole crew made the day easy and fun for everyone on board. The boat itself was comfortable and well-equipped. Highly recommend Mark and his team for anyone looking for a productive, well-run trip. We’ll be booking again!

    Laurie B. | July 28, 2026

    Trip: Key West 47 Ft Hatteras

  • ★★★★★
    Nick killed it!! Great fishing trip. If I’m ever back in the Keys, I will definitely go again!

    Jason E. | July 20, 2026

    Trip: Crushing Key West

  • ★★★★★
    We had a great time fishing. DJ was an excellent 1st Mate. He worked hard to make sure we caught a Mahi and he was a lot of fun!

    Holly H. | July 7, 2026

    Trip: Private Offshore Fishing

  • ★★★★★
    Mike and Cole were awesome! Even though it was a slow fishing day for everyone, we still caught some keepers and had a great time!

    Maggie M. | July 1, 2026

    Trip: Key West Fishing More Than 6 Paxs

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Last updated: August 7, 2026

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See All Deep Dropping Trips in the Florida Keys