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

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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 Monster Catch

100% (6)
31 ft 1 - 12 People From $1,495
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Cudjoe Key

All-Inclusive Fishing Adventure

100% (1)
34 ft 1 - 6 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Layton

Layton Fishing Adventure

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

Deep Sea, Nearshore Fishing in Key Largo

Keys All-Day Adventure!

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

Deep Sea, Nearshore Fishing in Key West

Legendary Fishing In Key West

100% (25)
55 ft 1 - 6 People From $1,100
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Runnin' The Dry Tortugas

100% (12)
33 ft 1 - 6 People From $2,800

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 in Key West

Dry Tortugas Smash

95% (22)
33 ft 1 - 6 People From $2,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Little Torch Key

Reef Fishing Little Torch Key

100% (24)
30 ft 1 - 6 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea Fishing in Key West

Laid Back Key West

100% (12)
33 ft 1 - 6 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key Largo

Swordfish Slam

100% (8)
35 ft 1 - 6 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

All-Day Deep Dropping Thriller

100% (1)
48 ft 1 - 6 People From $2,500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Key West Big Game Fishing

100% (1)
34 ft 1 - 6 People From $1,500
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 22 deep dropping trips in the Florida Keys, and the most popular trips in the area are Marquesas Key Fishing Adventure guided by Anthony, Key West Nearshore/Offshore Trip guided by Mike, and Gulf - Shrimp Boats & Wrecks guided by John.

Our guides in the Florida Keys are rated a 4.88 out of 5 based on 4519 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. wahoo.

How much do Florida Keys deep dropping fishing charters cost?

Prices for deep dropping in the Florida Keys can range anywhere from about $1,070 to $3,008, but the average price for a half day trip for deep dropping in the Florida Keys is $1,440. The average price for a full day trip for deep dropping in the Florida Keys is $2,209.

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

  • ★★★★★
    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

  • ★★★★★
    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. | July 16, 2024

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    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. | June 25, 2024

    Trip: Key West Nearshore/Offshore Trip

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

    Stephen M. | June 22, 2024

    Trip: Legendary Fishing in Key West

Other Fishing Techniques in the Florida Keys

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See All Deep Dropping Trips in the Florida Keys