Damn Good Deep Dropping Charters In Big Pine Key

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

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Recently Booked Deep Dropping Charters In Big Pine 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 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

Inshore, Deep Sea Fishing in Big Pine Key

Big Pine Wreck And Reef Fishing

100% (2)
25 ft 1 - 12 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Big Pine Key

Big Pine Offshore Fishing

100% (2)
25 ft 1 - 12 People From $1,150
Bucket List
The Captain Experiences team chose this trip as one for the bucket list.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Dry Tortugas Fishing Trip

100% (11)
36 ft 1 - 6 People From $2,800
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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Flats in Marathon

Full Day (8hr)

100% (4)
27 ft 1 - 8 People From $1,200

Top Types of Deep Dropping Trips in Big Pine Key

Top Species for Deep Dropping in Big Pine 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 Big Pine 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 Big Pine 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 Fishing in Marathon

Mahi / Offshore Combo

100% (9)
35 ft 1 - 6 People From $1,600
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Little Torch Key

Reef Fishing Little Torch Key

100% (27)
30 ft 1 - 6 People From $750
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, Jetty in Key West

Ultimate Action Fishing In Key West

100% (18)
33 ft 1 - 12 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% (8)
50 ft 1 - 12 People From $950
See All Deep Dropping Trips in Big Pine Key

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Everything to Know About Booking a Big Pine Key deep dropping charter

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

Our Damn Good Guides currently offer 46 deep dropping trips in Big Pine Key, and the most popular trips in the area are Florida Keys Destination Fishing guided by Alex, Big Pine Wreck And Reef Fishing guided by Tom, and Big Pine Offshore Fishing guided by Tom.

Our guides in Big Pine 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 Big Pine Key? Check out our beginner and family friendly deep dropping guides in Big Pine Key.

What types of deep dropping charters are common in Big Pine Key?

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

The most commonly sought after species for deep dropping in Big Pine Key are: 1. gag grouper, 2. goliath grouper, 3. lane snapper, 4. mahi mahi, and 5. mutton snapper.

How much do Big Pine Key deep dropping fishing charters cost?

Prices for deep dropping in Big Pine Key can range anywhere from about $1,300 to $3,600, but the average price for a half day trip for deep dropping in Big Pine Key is $1,577. The average price for a full day trip for deep dropping in Big Pine Key is $3,264.

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 Big Pine Key?

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

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

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

View Big Pine Key Fishing Reports from our damn good guides.

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See All Deep Dropping Trips in Big Pine Key