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
4.85/5 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

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Key West Fishing Experience

100% (4)
32 ft 1 - 8 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Key West Fishing Trip

100% (11)
36 ft 1 - 6 People From $2,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Runnin' The Dry Tortugas

100% (14)
33 ft 1 - 6 People From $2,800
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% (18)
33 ft 1 - 4 People From $1,600
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
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

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

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
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% (106)
40 ft 1 - 6 People From $1,400
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 Fishing in Key West

Sportfishing Key West

100% (8)
50 ft 1 - 12 People From $950
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

Inshore, Deep Sea Fishing in Key West

Laid Back Key West

100% (14)
33 ft 1 - 6 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Ultimate Action Fishing

100% (2)
30 ft 1 - 12 People From $900
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 37 deep dropping trips in Key West, and the most popular trips in the area are Key West Fishing Experience guided by Joe, Key West Fishing Trip guided by Rob, and Runnin' The Dry Tortugas guided by Eric.

Our guides in Key West are rated a 4.85 out of 5 based on 5945 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 deep sea fishing, nearshore fishing, and inshore fishing.

The most commonly sought after species for deep dropping in Key West are: 1. amberjack, 2. barracuda, 3. blackfin tuna, 4. blue marlin, and 5. cobia.

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 $3,600, but the average price for a half day trip for deep dropping in Key West is $1,585. The average price for a full day trip for deep dropping in Key West is $3,415.

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

  • ★★★★★
    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

  • ★★★★★
    We had an absolutely unforgettable day on the water with Captain Mason! Our family of six—ranging from more "seasoned" to children—was treated to a private fishing excursion that truly exceeded all expectations. From the moment we stepped on the boat, the Mason made us feel completely at ease. He was incredibly accommodating, making sure each of us was comfortable, engaged, and having a great time. Whether it was adjusting for the kids' needs, helping with baiting hooks, or offering fishing tips to the beginners among us, his patience and positive energy never wavered. What stood out the most was how safe and inclusive he made the entire experience. Every member of the family felt like part of the crew. He kept a watchful eye on everything while still creating a laid-back, fun atmosphere. We never once felt rushed or out of place—just fully present and enjoying every moment. He also went above and beyond in every possible way—from extending our time a bit when the fish were biting to showing us local wildlife and secret spots only a seasoned pro would know. It truly felt like a one-of-a-kind adventure curated just for us. Highly recommend this charter to anyone looking for a fun, family-friendly, and expertly guided day on the water. Can’t wait to book again next time we’re in town!

    Lee D. | July 10, 2025

    Trip: Dry Tortugas Fishing Trip

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:

See All Deep Dropping Trips in Key West