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

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 in Key West

Key West 47 Ft Hatteras

99% (106)
47 ft 1 - 6 People From $1,300
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Key West Fishing Experience

100% (4)
32 ft 1 - 8 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Stock Island

10 Hr Swordfishing

NEW
33 ft 1 - 4 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key Largo

Key Largo Epic Fishing

100% (9)
36 ft 1 - 6 People From $1,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Stock Island

Key West Nearshore/Offshore Trip

100% (34)
63 ft 1 - 12 People From $1,850
Hot Trip
people are viewing this trip.
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

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

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

Inshore, Deep Sea, Nearshore in Marathon

Offshore Marathon

100% (11)
31 ft 1 - 12 People From $1,495
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Gulf - Shrimp Boats & Wrecks

96% (27)
32 ft 1 - 6 People From $2,250
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Reef And Wrecks

NEW
37 ft 1 - 12 People From $900
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Little Torch Key

Reef Fishing Little Torch Key

100% (27)
30 ft 1 - 6 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Swordfish / Trolling

NEW
37 ft 1 - 12 People From $1,300
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 Marathon

Mahi / Offshore Combo

100% (9)
35 ft 1 - 6 People From $1,600
See All Deep Dropping Trips in the Florida Keys

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Everything to Know About Booking a Florida Keys deep dropping charter

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

Our Damn Good Guides currently offer 23 deep dropping trips in the Florida Keys, and the most popular trips in the area are Key West 47 Ft Hatteras guided by Mark, Key West Fishing Experience guided by Joe, and 10 Hr Swordfishing guided by Julien.

Our guides in the Florida Keys are rated a 4.86 out of 5 based on 5945 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 deep sea fishing, nearshore fishing, and inshore fishing.

The most commonly sought after species for deep dropping in the Florida Keys are: 1. african pompano, 2. albacore tuna, 3. amberjack, 4. barracuda, and 5. blackfin tuna.

How much do Florida Keys deep dropping fishing charters cost?

Prices for deep dropping in the Florida Keys can range anywhere from about $1,200 to $3,600, but the average price for a half day trip for deep dropping in the Florida Keys is $1,505. The average price for a full day trip for deep dropping in the Florida Keys is $2,494.

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 55 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

  • ★★★★★
    Wonderful trip, they made it so easy to enjoy ourselves, crew was inviting and welcoming. will definitely be booking again

    Heather W. | November 27, 2025

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    Outstanding

    Jodie R. | October 9, 2025

    Trip: Key West Offshore Action

  • ★★★★★
    Great time fishing the captain was very nice and very knowledgeable about his business fishing. I would definitely go again with him

    John V. | August 29, 2025

    Trip: Reef Fishing Little Torch Key

  • ★★★★★
    My wife and I had the pleasure of taking a trip with Captain George. He and his mate Kyle picked us up on time and took us out for a great day of fishing. Weather was definitely sporty but his boat handled it comfortably. They were very well prepared to for everything. Having a boat myself I asked a lot of questions on techniques and such. Captain George was very help and wasn't hesitant to share his knowledge. We had a great time. They were upbeat and personable. We ended up will a cooler full of yellow tail snapper, a nice mutton snapper, a nice fight on a good-sized bonito. They recommended a good place to cook it up for us. I would highly recommend taking a trip with Captain George.

    Andy T. | August 15, 2025

    Trip: Layton Fishing Adventure

  • ★★★★★
    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

Other Fishing Techniques in the Florida Keys

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See All Deep Dropping Trips in the Florida Keys