Damn Good Deep Dropping Charters In Key West

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

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Recently Booked Deep Dropping Charters In Key West, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Morning 1/2 Day Fishing Charter

94% (17)
25 ft 1 - 4 People From $800
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 Key West

Sportfishing Key West

100% (6)
50 ft 1 - 12 People From $950
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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Key West

4 Hour Private Fishing

100% (1)
28 ft 1 - 6 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Pulley Ridge

96% (23)
37 ft 1 - 6 People From $5,500
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 Deep Sea Run - 40' Luhrs

99% (93)
40 ft 1 - 6 People From $1,400

Top Types of Deep Dropping Trips in Key West

Top Species for Deep Dropping in Key West

“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.”

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Target Species in Key West

View Full Species Seasonality Chart »
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

More Deep Dropping Charters In Key West, Fl

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 Key West

Hidden Fishing Gems Of The Dry Tortugas

100% (15)
33 ft 1 - 4 People From $2,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Key West

8 Hour Private Fishing

100% (1)
28 ft 1 - 6 People From $1,350
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 Key West

Reef Fishing Key West

100% (6)
50 ft 1 - 6 People From $950
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 in Key West

10 HR Swordfish/Trolling/Deep-Drop

NEW
40 ft 1 - 6 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Gulf - Shrimp Boats & Wrecks

96% (23)
33 ft 1 - 6 People From $2,250
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 Key West

Federal Gulf Waters

100% (70)
30 ft 1 - 12 People From $1,550
See All Deep Dropping Trips in Key West

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Everything to Know About Booking a Key West deep dropping charter

Why should I book a deep dropping charter in Key West with Captain Experiences?

Our Damn Good Guides currently offer 31 deep dropping trips in Key West, and the most popular trips in the area are Key West fishing Trip guided by Rob, Pulley ridge guided by John, and Key West Big Game Fishing guided by Brad.

Our guides in Key West are rated a 4.86 out of 5 based on 4713 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 Key West? Check out our beginner and family friendly deep dropping guides in Key West.

What types of deep dropping charters are common in Key West?

Deep Sea fishing is the most popular type of fishing for deep dropping in Key West as well as nearshore fishing, inshore fishing, and jetty fishing.

The most commonly sought after species for deep dropping in Key West are: 1. mutton snapper, 2. yellowtail snapper, 3. sailfish, 4. blackfin tuna, and 5. black grouper.

How much do Key West deep dropping fishing charters cost?

Prices for deep dropping in Key West can range anywhere from about $1,150 to $3,200, but the average price for a half day trip for deep dropping in Key West is $1,595. The average price for a full day trip for deep dropping in Key West is $2,329.

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 Key West?

The most popular season to go on a deep dropping charter in Key West is summer, and most anglers book their trips 34 days in advance.

Do I need a Key West fishing license and what are the bag limits in Key West?

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

Recent Reviews

  • ★★★★★
    Everything about our trip was outstanding! The boat, the Captian, Captain Carlson was fantastic. He wanted fish for every one of us on the boat even more than we wanted to catch! He worked so hard to load the boat and that we did!!! One of the best charters I have even been one. We all can’t wait to come back again and do it all over again!

    Kip J. | June 1, 2025

    Trip: Dry Tortugas fishing Trip

  • ★★★★★
    We had a great time with mason-fun day on the water

    Blaine W. | March 19, 2025

    Trip: Dry Tortugas fishing Trip

  • ★★★★★
    Captain Anthony was awesome! Great with the kids and adults alike. The weather wasn't cooperating on our trip but he still managed to put us some fish even if wasn't our target for the day. I would fish with Captain Anthony again anytime!

    Jb H. | January 7, 2025

    Trip: Ultimate Action Fishing in Key West

  • ★★★★★
    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

Other Fishing Techniques in Key West

How are fishing conditions in Key West?

View Key West Fishing Reports from our damn good guides.

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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 Key West