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.

Choose a Date
4.86/5 Average Rating

Damn Good Guides

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

Experts Available 24/7

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

100% Weather Guarantee

We want to keep everyone safe, so in the case of inclement weather we'll work with you to reschedule at no cost

Recently Booked Deep Dropping Charters In Key West, Fl

Hot Trip
people are viewing this trip.
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 West

Pulley Ridge

96% (27)
37 ft 1 - 6 People From $5,500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Morning 1/2 Day Fishing Charter

94% (18)
25 ft 1 - 4 People From $800
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
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% (12)
36 ft 1 - 6 People From $1,000
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore, Jetty in Key West

Ultimate Action Fishing In Key West

100% (19)
33 ft 1 - 12 People From $800

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.”

Jonathan and Attison   |   Co-founders   |   Austin, Texas

All 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

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

Dry Tortugas Fishing Trip

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

Reef Fishing Key West

100% (8)
50 ft 1 - 6 People From $950
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
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Crushing Key West

100% (2)
30 ft 1 - 12 People From $900
Hot Trip
people are viewing this trip.
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
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 Gems Of The Dry Tortugas

100% (19)
33 ft 1 - 4 People From $2,400
See All Deep Dropping Trips in Key West

Need a Place to Stay?

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 39 deep dropping trips in Key West, and the most popular trips in the area are Long-Range Key West Trip guided by John, Pulley Ridge guided by John, and Morning 1/2 Day Fishing Charter guided by John.

Our guides in Key West are rated a 4.86 out of 5 based on 6405 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. blackfin tuna, 2. mutton snapper, 3. yellowtail snapper, 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 $1,300 to $4,000, but the average price for a half day trip for deep dropping in Key West is $1,644. The average price for a full day trip for deep dropping in Key West is $3,403.

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

  • ★★★★★
    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

  • ★★★★★
    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

  • ★★★★★
    The best

    Jodie R. | October 9, 2025

    Trip: Dry Tortugas Fishing Trip

  • ★★★★★
    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

Other Fishing Techniques in Key West

Other Featured Cities

How are fishing conditions in Key West?

View Key West Fishing Reports from our damn good guides.

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:

Enter to Win a

$500 DAMN GOOD GIFT CARD

Gift Card

Sign up to win $500 towards ANY trip. Winners drawn monthly.

By subscribing, you agree to receive marketing communications from Captain Experiences. To opt-out, click the unsubscribe button at the bottom of our emails. Privacy Policy and Terms & Conditions

See All Deep Dropping Trips in Key West