Damn Good Deep Dropping Charters In Islamorada

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Recently Booked Deep Dropping Charters In Islamorada, Fl

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Deep Sea, Nearshore Fishing in Islamorada

3/4 Day Trip Islamorada

100% (21)
44 ft 1 - 12 People From $1,500
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Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
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Fishing in Destin
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Deep Sea Fishing in Islamorada

Full Day Deep Sea

100% (7)
39 ft 1 - 12 People From $1,600
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Deep Sea, Nearshore Fishing in Islamorada

6 Hour 3/4 Day

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34 ft 1 - 12 People From $1,400
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 Islamorada

Extended Swordfish Trip

100% (20)
37 ft 1 - 6 People From $2,200
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Deep Sea, Nearshore Fishing in Islamorada

Best Islamorada Sportfishing

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

Keys Offshore Fishing Adventure

100% (35)
26 ft 1 - 4 People From $1,275

Top Types of Deep Dropping Trips in Islamorada

Top Species for Deep Dropping in Islamorada

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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

Fishing in Destin
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Deep Sea Fishing in Islamorada

10 Hour Trip – Swordfish

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34 ft 1 - 12 People From $2,200
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Deep Sea, Nearshore Fishing in Islamorada

4 Hour Half Day

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34 ft 1 - 12 People From $1,100
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Deep Sea, Nearshore Fishing in Islamorada

Full Day Islamorada Trip

100% (21)
44 ft 1 - 12 People From $1,800
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Deep Sea, Nearshore Fishing in Islamorada

Afternoon Half

100% (21)
44 ft 1 - 12 People From $1,100
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Deep Sea Fishing in Islamorada

8 Hour Full Day

NEW
34 ft 1 - 12 People From $750
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.
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Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

3/4 Day Deep Sea

100% (7)
39 ft 1 - 12 People From $1,300
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Everything to Know About Booking an Islamorada deep dropping charter

What are the best deep dropping charters in Islamorada?

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 Trip Islamorada guided by Troy, Full Day Deep Sea guided by Timothy, and 6 Hour 3/4 Day guided by Cole.

Our guides in Islamorada are rated a 4.96 out of 5 based on 7151 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 nearshore fishing.

The most commonly sought after species for deep dropping in Islamorada are: 1. blackfin tuna, 2. kingfish, 3. mahi mahi, 4. sailfish, and 5. yellowtail snapper.

How much do Islamorada deep dropping fishing charters cost?

Prices for deep dropping in Islamorada can range anywhere from about $1,100 to $3,400, but the average price for a half day trip for deep dropping in Islamorada is $1,633. The average price for a full day trip for deep dropping in Islamorada is $2,492.

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

  • ★★★★★
    Awesome time with Jim plenty of snapper to go around

    Jonas P. | May 6, 2026

    Trip: Key Largo Reef And Offshore

  • ★★★★★
    Had a great day with Captain Dan and first mate. We pomptly set off and had a fantastic time pulling in a Mahi and half a dozen tuna. The trip was as much as we hoped for…good weather, great crew, and some fish to be cooked at a local restaurant. Highly recommend this charter and will definitely be booking again for some other fishing if/when we make it back to the Keys. Thanks Dan and Pete!

    Adam M. | April 8, 2026

    Trip: Deep Sea, Wreck And Reef

  • ★★★★★
    Booked a 6 hour trip with my father and uncle and had a fantastic day. Weather was phenomenal and we were the first ones out on the water. We went out to troll the Islamorada Hump and were able to land a small blackfin tuna. On the way in, we hooked a 25-30 lb wahoo and had it right next to the boat but it bit through the mono leader. We then finished the day off catching fat yellowtails at the reef. Overall, solid day. TJ was a great captain and Mitch did a very good job at staying active on the lines. We had a great time and would recommend booking a trip with TJ.

    Julio R. | March 31, 2026

    Trip: 3/4 Day Deep Sea

  • ★★★★★
    Great time with capt Justin and Drew. Super knowledgeable and enjoyed our conversations. Although we only had three bites and two catches, we still enjoyed the day in the water and were able to take our tuna catch to a local restaurant for dinner which was amazing.

    Lisa P. | March 28, 2026

    Trip: Offshore Fishing Key Largo

  • ★★★★★
    We had an amazing day fishing with Captain Timothy (TJ) and his Mate Mitch. Their professionalism and willingness to go o above and beyond stood out the most. Awesome boat and crew who know him to find the fish. Thanks TJ.

    Steve G. | March 17, 2026

    Trip: 3/4 Day Deep Sea

Other Fishing Techniques in Islamorada

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