Damn Good Deep Dropping Charters In Key West

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

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Recently Booked Deep Dropping Charters In Key West

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Legendary Fishing In Key West

100% (8) Guided by Chuck
55 ft 1 - 6 People From $1,100
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Stock Island

Key West Nearshore/Offshore Trip

100% (6) Guided by Mike
63 ft 1 - 12 People From $1,850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Key West

Afternoon 1/2 Day Fishing

88% (8) Guided by John
25 ft 1 - 4 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

Inshore, Deep Sea, Nearshore, Jetty in Key West

Ultimate Action Fishing In Key West

100% (3) Managed by Anthony
33 ft 1 - 12 People From $800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Key West Offshore Action

89% (9) Guided by John
33 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, Nearshore Fishing in Key West

Key West To Dry Tortugas Charter

100% (2) Guided by Rob
36 ft 1 - 6 People From $1,400
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Top Types of Deep Dropping Trips in Key West

Top Species for Deep Dropping in Key West

“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

More Deep Dropping Charters In Key West

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Pulley Ridge

89% (9) Guided by John
37 ft 1 - 6 People From $5,500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Key West

6 Hour Private Fishing

NEW Guided by Noah
28 ft 1 - 6 People From $1,300
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

Dry Tortugas Smash

89% (9) Guided by John
33 ft 1 - 6 People From $2,400
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Key West

Full Day Private Fishing Charter

88% (8) Guided by John
25 ft 1 - 4 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Key West

Key West Fishing Experience

100% (2) Guided by Joe
32 ft 1 - 8 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Naval Air Station Key West

Key West Sportfishing Adventure!

100% (3) Guided by Craig
42 ft 1 - 6 People From $900
See All Deep Dropping Trips in Key West

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Everything to Know About Booking a Key West deep dropping charter

What are the best deep dropping charters in Key West?

The best deep dropping charters in Key West are:

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

Our Damn Good Guides currently offer 23 deep dropping trips in Key West, and the most popular trips in the area are Legendary Fishing in Key West guided by Chuck, Afternoon 1/2 day fishing guided by John, and Key West Nearshore/Offshore Trip guided by Mike.

Our guides in Key West are rated a 4.86 out of 5 based on 3816 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 Key West? Check out our beginner and family friendly deep dropping guides in Key West.

What types of deep dropping charters are common in Key West?

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

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

How much do Key West deep dropping fishing charters cost?

Prices for deep dropping in Key West can range anywhere from about $1,000 to $3,000, but the average price for a half day trip for deep dropping in Key West is $1,499. The average price for a full day trip for deep dropping in Key West is $2,182.

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 Key West?

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

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

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

Recent Reviews

  • ★★★★★
    We had a blast with Joe and Captain Chuck. Will definitely return!

    Yohannes H. | October 28, 2024

    Trip: Legendary Fishing in Key West

  • ★★★★★
    We had such a great time and our guide was fun, knowledgeable, and put us on the fish all trip! We will be going back for sure.

    Rae S. | October 6, 2024

    Trip: Key West Offshore Action

  • ★★★★★
    My families trip with Captain John was awesome. John is a humble, hardworking, easy going, chill, dude and fit right in with our families vibe. He was great with our 5 year old son and answered all of his many fishing questions. John made it clear that between the time of year and conditions that day we would have to really work at it to get anything. That’s exactly what we did and we ended up catching a good amount of fish. Most importantly our 5 year old son, who is obsessed with fishing, had the time of his life and caught fish he’s never seen before. 5 stars, highly recommend. If you have a small group this is the charter to go on!

    Jacob D. | August 25, 2024

    Trip: Full Day Private Fishing Charter

  • ★★★★★
    Great day on the water, Captain Mark and mate Will were awesome. They put me on fish and stayed out until the last minute. I would definitely recommend.

    Nicholas W. | August 8, 2024

    Trip: Key West Deep Sea Run - 40' Luhrs

  • ★★★★★
    Our charter with Captain John was incredible! He was very professional but also personable! We enjoyed everything about the fishing trip! We had a beautiful day & caught several large dolphins! Will definitely rebook with Capt. John the next time we are in Key West!

    Deanna H. | July 31, 2024

    Trip: Morning 1/2 Day Fishing Charter

  • ★★★★★
    We had an absolutely amazing time deep sea fishing with Captain Anthony! He is a fun and knowledgeable fisherman with LOTS of experience and great stories (ask him about how he’d dive for lobsters to impress his dates). He does all the work but lets you learn and participate as much or as little as you want. We knew we had an expert when we heard the radio chatter of all the other guides complaining that nothing was biting, while we pulled in six (only four mahi in pic). The other two were a small tuna and a ~32” barracuda). We highly recommend Kilo Whiskey Charter & Captain Anthony!

    Dan W. | July 18, 2024

    Trip: Ultimate Action Fishing in Key West

  • ★★★★★
    Absolutely the highlight of our trip. Mike and his crew were fantastic teachers, patient and focused on helping all of us catch terrific fish. They are great with kids of all ages - 5 years to 16 years. Everyone had a great time and we caught a lot of fish.

    Vicki L. | July 16, 2024

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    Capt John was top notch!! Our planned morning trip hit a snag due to bad weather…But John was honest and informative suggesting that we should hold off a few hours…so we did. Our afternoon ended up being an awesome fishing encounter. We would highly recommend…thank you Capt John!!!

    Kelly L. | July 1, 2024

    Trip: Morning 1/2 Day Fishing Charter

  • ★★★★★
    The family had an absolutely phenomenal time with Captain Mike and his crew. We caught plenty of fish. The crew was very helpful to the family. The boat was great. I will 100% recommend them to anyone looking for a great trip.

    Tommy L. | June 25, 2024

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    We had a great time on our first family fishing trip. We brought enthusiasm, and very little experience. John was a great teacher for all of us, and took us to several good spots in Lake Passage. We caught shark, black grouper and enough snapper to feast on for days. The fine folks at Hurricane Hole cooked it up for us and it was amazing!! We would definitely book another trip with John!!

    Karl H. | June 23, 2024

    Trip: Morning 1/2 Day Fishing Charter

  • ★★★★★
    Awesome experience. Captain chuck and Joe Joe were great. Nice boat, good times

    Stephen M. | June 22, 2024

    Trip: Legendary Fishing in Key West

  • ★★★★★
    Captain Mike and his crew were amazing!! We went out with 5 kids all under the age of 16 and they all caught fish and had a blast!!

    Fred S. | June 17, 2024

    Trip: Key West Nearshore/Offshore Trip

  • ★★★★★
    Mason was phenomenal. Easy to talk to, engaging, great at teaching, and fun to be with… we got Mahi-Mahi and an exotic. We had a blast and will go fishing with Mason again soon!!!

    Patrick C. | May 27, 2024

    Trip: Key West to Dry Tortugas Charter

  • ★★★★★
    Captain John was simply incredible! I have been fishing my entire life and know a great guide… Captain John is the real deal. He took the time to understand what we wanted to catch and then nailed it… put us on exactly what we wanted all day long. He was friendly, engaging and fun. We will be back to fish w Captain John again!!

    Patrick C. | May 26, 2024

    Trip: Morning 1/2 Day Fishing Charter

  • ★★★★★
    Great Trip. Would schedule another.

    David T. | May 9, 2024

    Trip: Reef Fishing

  • ★★★★★
    Had a great time today Caught a lot of fish. Thoroughly enjoyed our charter. Will return.

    Jorge E. | May 9, 2024

    Trip: Legendary Fishing in Key West

  • ★★★★★
    The best charter captain we have found and we have been on charters all over Fl.

    Theresa L. | May 5, 2024

    Trip: Reef Fishing

  • ★★★★★
    Has a great time. We all enjoyed

    Clayton S. | May 1, 2024

    Trip: Ultimate Action Fishing in Key West

  • ★★★★★
    Captain Allen was absolutely amazing! We have 3 children and he was so awesome with them and very accommodating! He took us out and showed us a wonderful time and we came back with a ton of fish!

    Sarah L. | April 25, 2024

    Trip: Reef Fishing

  • ★★★★★
    Mike and Cole were fantastic. We had four small kids with us, and they handled them perfectly. We caught lots of yellowtail snapper and a nurse shark! 10/10, would book again (and plan to).

    Daniel K. | April 3, 2024

    Trip: Key West Nearshore/Offshore Trip

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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:

See All Deep Dropping Trips in Key West