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

Hot Trip
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Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Long-Range Key West Trip

96% (27)
32 ft 1 - 6 People From $1,350
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
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

Private Offshore Fishing

100% (3)
34 ft 1 - 6 People From $950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Layton

Layton Fishing Adventure

100% (6)
27 ft 1 - 4 People From $850
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 Marathon

Tarpon Trips Marathon

100% (18)
34 ft 1 - 12 People From $1,200
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people are viewing this trip.
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

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, Nearshore Fishing in Islamorada

4 Hour Half Day

NEW
34 ft 1 - 12 People From $1,100
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
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Marathon

Offshore Marathon

100% (14)
31 ft 1 - 12 People From $1,495
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Dry Tortugas Smash

96% (27)
32 ft 1 - 6 People From $2,400
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 in Key West

Key West 47 Ft Hatteras

99% (109)
47 ft 1 - 12 People From $1,300
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Runnin' The Dry Tortugas

100% (15)
33 ft 1 - 6 People From $2,800
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 24 deep dropping trips in the Florida Keys, and the most popular trips in the area are Long-Range Key West Trip guided by John, Swordfish Slam guided by Eric, and Private Offshore Fishing guided by Joel.

Our guides in the Florida Keys are rated a 4.88 out of 5 based on 6501 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. yellowtail snapper, 3. mutton snapper, 4. sailfish, and 5. amberjack.

How much do Florida Keys deep dropping fishing charters cost?

Prices for deep dropping in the Florida Keys can range anywhere from about $1,250 to $3,920, but the average price for a half day trip for deep dropping in the Florida Keys is $1,826. The average price for a full day trip for deep dropping in the Florida Keys is $2,735.

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 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

  • ★★★★★
    Awsome time !!!

    David T. | March 16, 2026

    Trip: Private Offshore Fishing

  • ★★★★★
    I wish that I could give Joel and Tony more than 5 stars. We left the fishing trip with only 1 complaint and that was that we only booked it for 1 day. We absolutely will be back!!!

    Christopher C. | March 11, 2026

    Trip: Private Offshore Fishing

  • ★★★★★
    Captain George was the most knowledgeable of local water ways, weather, boats and ocean species. I have been on several charters and George is top-ranked in friendly, and responsible. George provided an excellent charter.

    Melissa K. | February 17, 2026

    Trip: Layton Fishing Adventure

  • ★★★★★
    Great experience-team was wonderful!

    Lori J. | February 16, 2026

    Trip: Offshore Marathon

  • ★★★★★
    Great trip Knowledge Captain and mate (Nels and CJ). Put us on the fish we targeted and mixed in a few othe rigs for variety. 5 stars, would do again.

    Tim R. | January 9, 2026

    Trip: Key West 47 Ft Hatteras

Other Fishing Techniques in the Florida Keys

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See All Deep Dropping Trips in the Florida Keys