Damn Good Deep Dropping Charters In Islamorada

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Recently Booked Deep Dropping Charters In Islamorada, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

3/4 Day Deep Sea

NEW
39 ft 1 - 12 People From $1,300
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 Islamorada

Afternoon Half

100% (19)
44 ft 1 - 12 People From $1,100
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 Islamorada

Full Day Islamorada Trip

100% (19)
44 ft 1 - 12 People From $1,800
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, Nearshore Fishing in Islamorada

3/4 Day Trip Islamorada

100% (19)
44 ft 1 - 12 People From $1,500
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Full Day Deep Sea

NEW
39 ft 1 - 12 People From $1,600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Islamorada Deep Sea Trophy Hunt

100% (2)
45 ft 1 - 6 People From $950

Top Types of Deep Dropping Trips in Islamorada

Top Species for Deep Dropping in Islamorada

“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 Islamorada

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 Islamorada, Fl

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 Islamorada

Best Islamorada Sportfishing

100% (9)
43 ft 1 - 6 People From $1,300
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 Islamorada

Extended Swordfish Trip

100% (17)
37 ft 1 - 6 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Half Day Deep Sea

NEW
39 ft 1 - 12 People From $1,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Keys Offshore Fishing Adventure

100% (32)
26 ft 1 - 4 People From $1,275
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key Largo

Swordfish Slam

100% (10)
35 ft 1 - 6 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Marathon

Full Day Marathon Fishing

100% (3)
42 ft 1 - 6 People From $1,200
See All Deep Dropping Trips in Islamorada

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Everything to Know About Booking an Islamorada deep dropping charter

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

Our Damn Good Guides currently offer 23 deep dropping trips in Islamorada, and the most popular trips in the area are 3/4 Day Deep Sea guided by Timothy, Afternoon Half guided by Troy, and Full Day Islamorada Trip guided by Troy.

Our guides in Islamorada are rated a 4.93 out of 5 based on 5941 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 Islamorada? Check out our beginner and family friendly deep dropping guides in Islamorada.

What types of deep dropping charters are common in Islamorada?

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

The most commonly sought after species for deep dropping in Islamorada are: 1. african pompano, 2. amberjack, 3. barracuda, 4. blackfin tuna, and 5. cero mackerel.

How much do Islamorada deep dropping fishing charters cost?

Prices for deep dropping in Islamorada can range anywhere from about $1,000 to $3,120, but the average price for a half day trip for deep dropping in Islamorada is $1,416. The average price for a full day trip for deep dropping in Islamorada is $2,199.

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 Islamorada?

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

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

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

Recent Reviews

  • ★★★★★
    My wife and I had the pleasure of taking a trip with Captain George. He and his mate Kyle picked us up on time and took us out for a great day of fishing. Weather was definitely sporty but his boat handled it comfortably. They were very well prepared to for everything. Having a boat myself I asked a lot of questions on techniques and such. Captain George was very help and wasn't hesitant to share his knowledge. We had a great time. They were upbeat and personable. We ended up will a cooler full of yellow tail snapper, a nice mutton snapper, a nice fight on a good-sized bonito. They recommended a good place to cook it up for us. I would highly recommend taking a trip with Captain George.

    Andy T. | August 15, 2025

    Trip: Layton Fishing Adventure

  • ★★★★★
    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

  • ★★★★★
    Fantastic trip with Captain Troy and First Mate Mark!

    Leigh A. | July 5, 2025

    Trip: 3/4 Day Trip Islamorada

  • ★★★★★
    This was honestly one of the most disappointing charters I’ve had. I’ve booked numerous charters all over and in the keys. I realize fishing is fishing but we were greeted by a captain other than Dan, great guy but not what I expected honestly. Our vessel wasn’t prepared and ready to go so we waited longer than was expected and it pushed other plans back even further. We caught one 12.5 inch yellow that was big enough to keep. On other charters the boat is quite well prepared and ready to change course quickly to get you on the fish, not the case, granted it was a shorter booking I’ve still had much better equipped captains and vessels. So to spend the day bobbing for non existent apples was not at all ideal. It was so boring my wife and son chose to nap. So just be aware that if you choose this charter it may not go at all to plan. Sadly it was a waste of precious vacation time. I typically hate reading negative reviews and have never personally left one, but this seemed appropriate given the outcome. Good luck.

    Darren H. | March 14, 2025

    Trip: Deep Sea, Wreck And Reef

  • ★★★★★
    Captain Dan and Ryan were fantastic. The ocean was pretty rough that day but they helped us have a great time and pull in quite a few fish. We’ll be back again next year and will definitely look to hire them again!

    Moira V. | November 8, 2024

    Trip: Deep Sea, Wreck And Reef

Other Fishing Techniques in Islamorada

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How are fishing conditions in Islamorada?

View Islamorada Fishing Reports from our damn good guides.

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See All Deep Dropping Trips in Islamorada