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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4.88/5 Average Rating

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

Big Pine Offshore Fishing

100% (4)
25 ft 1 - 12 People From $1,200
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

Inshore, Deep Sea Fishing in Big Pine Key

Big Pine Wreck And Reef Fishing

100% (4)
25 ft 1 - 12 People From $750
Hot Trip
people are viewing this trip.
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, Flats in Big Pine Key

Full Day (8hr)

100% (5)
27 ft 1 - 8 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Little Torch Key

3/4 Or Full Day Trip

100% (4)
33 ft 1 - 6 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Little Torch Key

Reef Fishing Little Torch Key

100% (33)
30 ft 1 - 6 People From $750

Top Types of Deep Dropping Trips in Big Pine Key

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 Big Pine Key

All Target Species in Big Pine Key

  • 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

Deep Sea Fishing in Summerland Key

Summerland Key Offshore 34 Sea Vee

NEW
34 ft 1 - 6 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Cudjoe Key

Mahi, Tuna & Wahoo Adventure

100% (1)
32 ft 1 - 12 People From $1,650
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Cudjoe Key

Bucket List Swordfish Expedition

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

Deep Sea Fishing in Marathon

Marathon Key Swordfish Hunt

100% (22)
32 ft 1 - 12 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Offshore

100% (22)
32 ft 1 - 12 People From $1,600
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 Fishing in Marathon

Mahi / Offshore Combo

100% (14)
35 ft 1 - 6 People From $1,600

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 Big Pine Key deep dropping charter

What are the best deep dropping charters in Big Pine Key?

The best deep dropping charters in Big Pine Key are:

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

Our Damn Good Guides currently offer 48 deep dropping trips in Big Pine Key, and the most popular trips in the area are Big Pine Offshore Fishing guided by Tom, Big Pine Wreck And Reef Fishing guided by Tom, and Florida Keys Destination Fishing guided by Alex.

Our guides in Big Pine Key are rated a 4.88 out of 5 based on 8353 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 inshore fishing and flats fishing.

The most commonly sought after species for deep dropping in Big Pine Key are: 1. red snapper, 2. african pompano, 3. amberjack, 4. black grouper, 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 $1,350 to $4,200, but the average price for a half day trip for deep dropping in Big Pine Key is $1,769. The average price for a full day trip for deep dropping in Big Pine Key is $3,374.

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 guide will always know all the relevant rules and regulations in Big Pine Key.

Recent Reviews

  • ★★★★★
    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

  • ★★★★★
    Great mate/captain. Very knowledgeable, works hard, knows the fishing spots and will make sure you will catch a lot. Boat is great/ would do again/highly recommend!

    Francesco A. | June 16, 2026

    Trip: Private Offshore Fishing

  • ★★★★★
    We booked an eight hour trip. The captain was amazing and would book him again for sure. We caught a bunch of yellow tail snapper and my youngest son caught a 47lb cobia.

    Angela R. | June 9, 2026

    Trip: Big Pine Wreck And Reef Fishing

  • ★★★★★
    We booked a fishing charter for my husband 60th birthday, and it turned out to be one of the highlights of our trip! Kevin and Max were absolutely awesome! Friendly knowledgeable, professional and committed to making sure everyone had a great time. They put us on the fish and we wound up catching a barracuda and a tuna, which made the day that much more exciting. The best part was bringing our fresh tuna to Kaya restaurant where they prepared it three different ways. It was an incredible experience from start to finish. If you are considering a fishing charter, we highly recommend Captain Experiences and especially Kevin and Max. Thank you for making my husband 60th birthday so special. Looking forward to doing this again!

    Ellie G. | June 2, 2026

    Trip: Key West Fishing More Than 6 Paxs

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Last updated: July 17, 2026

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