Damn Good Deep Dropping Charters In The Caribbean Sea

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

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4.89/5 Average Rating

Recently Booked Deep Dropping Charters In The Caribbean Sea

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in El Combate

Combate Private Fishing Charter

100% (4)
26 ft 1 - 12 People From $1,208
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Rincon

Epic Sportfishing - Rincon, PR

100% (4)
26 ft 1 - 6 People From $1,208
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in San Juan

50' Offshore Fishing Cap Cana DR

94% (95)
50 ft 1 - 6 People From $2,700
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Caguas

San Juan Offshore - 42’ Egg Harbour

94% (95)
42 ft 1 - 6 People From $950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Carolina

Offshore Fishing Loiza PR

100% (26)
35 ft 1 - 6 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Palmas del Mar

Deep Water Seamounts

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

Top Types of Deep Dropping Trips in the Caribbean Sea

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Damn Good Guides

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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 the Caribbean Sea

More Deep Dropping Charters In The Caribbean Sea

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Boat Cruise in Roosevelt Roads

Professional Fishing & Beach

NEW
36 ft 1 - 12 People From $950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea in Roosevelt Roads

Let’s Go Deep

NEW
36 ft 1 - 6 People From $950
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Boat Cruise in Fajardo

6 Hr - Private Fishing Trip

100% (1)
37 ft 1 - 6 People From $1,250
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Boat Cruise in Fajardo

4 Hr - Private Fishing Trip

100% (1)
37 ft 1 - 6 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Utila

Slow-Pitch Jigging & Deep Drop

100% (1)
15 ft 1 - 2 People From $240
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Jolly Harbour

Deep Sea Fishing Charter

NEW
34 ft 1 - 5 People From $650

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 Caribbean Sea deep dropping charter

What are the best deep dropping charters in the Caribbean Sea?

The best deep dropping charters in the Caribbean Sea are:

Why should I book a deep dropping charter in the Caribbean Sea with Captain Experiences?

Our Damn Good Guides currently offer 20 deep dropping trips in the Caribbean Sea, and the most popular trips in the area are Combate Private Fishing Charter guided by Frank, Epic Sportfishing - Rincon, PR guided by Frank, and 50' Offshore Fishing Cap Cana DR guided by Angel.

Our guides in the Caribbean Sea are rated a 4.89 out of 5 based on 9498 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 the Caribbean Sea? Check out our beginner and family friendly deep dropping guides in the Caribbean Sea.

What types of deep dropping charters are common in the Caribbean Sea?

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

The most commonly sought after species for deep dropping in the Caribbean Sea are: 1. wahoo, 2. mahi mahi, 3. blue marlin, 4. amberjack, and 5. sailfish.

How much do Caribbean Sea deep dropping fishing charters cost?

Prices for deep dropping in the Caribbean Sea can range anywhere from about $797 to $3,600, but the average price for a half day trip for deep dropping in the Caribbean Sea is $1,551. The average price for a full day trip for deep dropping in the Caribbean Sea is $2,191.

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 the Caribbean Sea?

The most popular season to go on a deep dropping charter in the Caribbean Sea is summer, and most anglers book their trips 26 days in advance.

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

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

Recent Reviews

  • ★★★★★
    Alberto was great today. He worked hard all day to find us a blue marlin. We had our chance at one but was unsuccessful. Thanks Brandon

    Brandon K. | June 30, 2026

    Trip: Deep Water Seamounts

  • ★★★★★
    Captain Fransisco was great and very knowledgeable.

    Tamera V. | January 5, 2026

    Trip: Offshore Fishing Loiza PR

  • ★★★★★
    Francisco was an excellent captain. Worked hard to make sure everyone was having fun and catching fish. Nice boat, good equipment and we went 2 for 3 on Mahi and caught & released 2 barracuda’s. Great day & highly recommend!

    Jr O. | December 29, 2025

    Trip: Offshore Fishing Loiza PR

  • ★★★★★
    Francisco was great! My wife enjoyed her first offshore excursion! We wil be back to fish again with Francisco.

    William C. | October 7, 2025

    Trip: Offshore Fishing Loiza PR

  • ★★★★★
    Frank maintained contact up to the day of the Charter. Arrived on time and well prepared. He was knowledgeable of the area and was a great experience. We caught tuna, wahoo, barracuda, red hind grouper, yellow jack, and trumpet fish. Definitely recommend Frank.

    Stephen S. | April 9, 2024

    Trip: Epic Sportfishing - Rincon, PR

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Last updated: October 8, 2026

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See All Deep Dropping Trips in the Caribbean Sea