Captain
Kerry Hennessy

Member since September 2023 Marathon, United States
Background
I am a 4th generation native Floridian and fisherman with a true passion for the water. I have been fishing in the Keys since 1993. These days I get the most joy giving my clients the experience of a lifetime and making forever memories.
Techniques
I am geared up for whatever is biting at the time. Fishing in the Keys is situational and specific species may be seasonal. The best part is something is always biting and I know where they live and how and when to target them.

Hey, I'm Captain Kerry Hennessy

Marathon, United States
Background
I am a 4th generation native Floridian and fisherman with a true passion for the water. I have been fishing in the Keys since 1993. These days I get the most joy giving my clients the experience of a lifetime and making forever memories.
Techniques
I am geared up for whatever is biting at the time. Fishing in the Keys is situational and specific species may be seasonal. The best part is something is always biting and I know where they live and how and when to target them.
Verified
Our Team
Marie K.
Business partner
Dez S.
Captain
Randy K.
Captain

My Charter Listings

Excellent
4.9 / 5
(108 reviews)
Marathon
 Instant Confirmation
Trips from US $775
Excellent
4.7 / 5
(1 review)
Marathon
 Last booking: 1 day ago
 Instant Confirmation
Trips from US $750

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 109 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (190)
Fishing with Kerry
Fishing with Kerry
Fishing with Kerry
+187
Angler rating
97
6
1
2
0
Anglers claimed
Good experience
95%
Friendly captain
98%
Recommend this charter
94%
Appropriate for children
97%
Satisfied with the boat
97%
Caught fish
98%
Sort by:
Featured  
Showing:
5 of 109 reviews
Sean H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

4 hour trip with Captain Dez

VERIFIED   4 Hour Reef and Wreck Trip on October 12, 2025
We had a great 4 hour trip with Captain Dez and Mate Jose. Dez had us on the fish within 20-25 minutes of leaving the dock,...
Sean H. recommends Hennessy Sportfishing - Mako 28
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Gary B.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

BEST day, BEST experience!

VERIFIED   6 Hour Reef and Wreck Trip on November 15, 2025
Dez and Jose helped make my dreams come true today. Deep sea fishing has been at the top of my bucket list all of my life and...
Gary B. recommends Hennessy Sportfishing - Mako 28
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George H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Targeting Snapper

VERIFIED   4 Hour Reef and Wreck - (PM) trip on November 7, 2025
Our original plan was to focus on Yellowtail & Mutton snapper and then go after bigger fish. We got several Yellowtails immediately,...
George H. recommends Hennessy Sportfishing - Mako 28
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Shaun H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Awesome day of catching!

VERIFIED   6 Hour - (PM) Trip on March 10, 2026
Captain Dez & Captain Dillon provided an amazing variety of action packed fishing from sharks to snapper and everything in...
Shaun H. recommends Hennessy Sportfishing - Mako 28
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Mark R.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Choppy day but the bite was on

VERIFIED   4 Hour Reef and Wreck - (PM) trip on March 9, 2026
Captain Erik worked hard to make sure our party of 6 was well taken care of. Very positive and upbeat vibe, saw plenty of fish...
Mark R. recommends Hennessy Sportfishing - Mako 28
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