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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4.91/5 Average Rating

Recently Booked Deep Dropping Charters In Key West, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Full Day Offshore Extreme Fishing

100% (2)
35 ft 1 - 12 People From $2,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Crushing Key West

100% (3)
30 ft 1 - 12 People From $900
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, Nearshore Fishing in Key West

Marquesas Key Fishing Adventure

100% (21)
33 ft 1 - 4 People From $1,600
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 Fishing Trip

100% (16)
36 ft 1 - 6 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

Deep Sea Fishing in Key West

Federal Gulf Waters

100% (100)
30 ft 1 - 12 People From $1,550
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Key West

Hidden Gems Of The Dry Tortugas

100% (21)
33 ft 1 - 4 People From $2,400

Top Types of Deep Dropping Trips in Key West

What makes Captain Experiences Damn Good?

Damn Good Guides

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

Damn Good Guides

Experts Available 24/7

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

Experts Available 24/7

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We want to keep everyone safe, so if the weather is bad we'll work with you to reschedule at no cost.

100% Weather Guarantee

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 Key West

All Target Species in Key West

  • 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

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

6 Hour Offshore Extreme Fishing

100% (2)
35 ft 1 - 12 People From $1,600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Key West Sea Hunter

100% (37)
40 ft 1 - 6 People From $950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Key West

Key West Fishing At Its Finest

100% (37)
37 ft 1 - 12 People From $1,050
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% (126)
47 ft 1 - 12 People From $1,300
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Dry Tortugas Multi-Day Trip

NEW
50 ft 1 - 12 People From $5,900
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Private Offshore Fishing

100% (11)
34 ft 1 - 6 People From $1,000

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 Key West deep dropping charter

What are the best deep dropping charters in Key West?

The best deep dropping charters in Key West are:

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

Our Damn Good Guides currently offer 38 deep dropping trips in Key West, and the most popular trips in the area are Full Day Offshore Extreme Fishing guided by Samuel, Crushing Key West guided by Nick, and Marquesas Key Fishing Adventure guided by Anthony.

Our guides in Key West are rated a 4.91 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 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. red snapper, 2. mutton snapper, 3. blackfin tuna, 4. sailfish, and 5. wahoo.

How much do Key West deep dropping fishing charters cost?

Prices for deep dropping in Key West can range anywhere from about $1,400 to $4,200, but the average price for a half day trip for deep dropping in Key West is $1,833. The average price for a full day trip for deep dropping in Key West is $3,527.

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 spring, 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 guide will always know all the relevant rules and regulations in Key West.

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 Key West