Damn Good Deep Dropping Charters In Cudjoe Key

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

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4.86/5 Average Rating

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Recently Booked Deep Dropping Charters In Cudjoe Key, Fl

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
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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Offshore Fishing

100% (3)
33 ft 1 - 12 People From $1,150
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
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 Marathon

3/4 Day

100% (11)
34 ft 1 - 6 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 47 Ft Hatteras

99% (106)
47 ft 1 - 6 People From $1,300

Top Types of Deep Dropping Trips in Cudjoe Key

Top Species for Deep Dropping in Cudjoe Key

“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 Cudjoe Key

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 Cudjoe Key, 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 Fishing in Key West

Sportfishing Key West

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

Deep Sea, Nearshore Fishing in Stock Island

Key West Nearshore/Offshore Trip

100% (34)
63 ft 1 - 12 People From $1,850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Key West Offshore Action

96% (27)
32 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 Big Pine Key

Florida Keys Destination Fishing

100% (4)
28 ft 1 - 8 People From $1,000
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 Fishing in Marathon

Mahi / Offshore Combo

100% (9)
35 ft 1 - 6 People From $1,600
See All Deep Dropping Trips in Cudjoe Key

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Everything to Know About Booking a Cudjoe Key deep dropping charter

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

Our Damn Good Guides currently offer 44 deep dropping trips in Cudjoe Key, and the most popular trips in the area are All-Inclusive Fishing Adventure guided by Jose, Key West Deep Sea Run - 40' Luhrs guided by Mark, and Offshore Fishing guided by Aaron.

Our guides in Cudjoe Key are rated a 4.86 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 Cudjoe Key? Check out our beginner and family friendly deep dropping guides in Cudjoe Key.

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

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

The most commonly sought after species for deep dropping in Cudjoe Key are: 1. amberjack, 2. black grouper, 3. blackfin tuna, 4. blue marlin, and 5. hammerhead shark.

How much do Cudjoe Key deep dropping fishing charters cost?

Prices for deep dropping in Cudjoe Key can range anywhere from about $1,300 to $3,600, but the average price for a half day trip for deep dropping in Cudjoe Key is $1,585. The average price for a full day trip for deep dropping in Cudjoe Key is $3,283.

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 Cudjoe Key?

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

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

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

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 awesome day with Captain Aaron. He dialed up the perfect weather. We caught a bunch of fish, including this 25 pound bull.

    Todd H. | July 14, 2025

    Trip: Offshore Fishing

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How are fishing conditions in Cudjoe Key?

View Cudjoe Key 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.

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See All Deep Dropping Trips in Cudjoe Key