Capt. Trentin Leary 

4.9/5 (118 reviews)
 
State licensed
 79851 Overseas Highway, Islamorada, FL 33036, United States

Capt. Trentin Leary 

 
State licensed
4.9/5 (118)
 Angler's Choice
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79851 Overseas Highway
Islamorada, FL, United States
You may qualify for a Loyalty Program discount with Capt. Trentin Leary. To check if you can use a Loyalty Program discount for your selected dates, please sign in.

Capt. Trentin Leary is located in Islamorada and would love to show you a memorable time on these waters! 

You're looking at 4 to 8-hour trips most of the time, where you'll go after the likes of Tarpon, Snapper, Snook, Redfish, Permit, and Grouper, and more depending on the weather and time of year.  Capt. Trentin is a big fan of live bait fishing and will often bring live shrimp from the marina, and many days catch live pilchards or mullet to use to give you a better opportunity at catching quality fish!

Your boat for the day will be a classic 1977 (restored in 2024) custom 22' SeaCraft center console that can comfortably fish and seat 3 anglers. We will book trips with 4 anglers, however this is usually best with two adults and two kids on half day trips.  Seating options are limited and one person will have to be standing and holding the leaning post while running with 4 guests, so be aware of that.  We do not recommend booking with 4 guests where everyone will require a seat for the whole trip or for guests that have difficulty maneuvering around.

The boat comes with an ice box and is outfitted with a 200 HP Yamaha outboard to get you to the fish quickly.  SeaCraft boats have a great reputation as being comfortable boats and the 70's models are very desirable for restoration project boats.

All the necessary fishing gear is included in the price of your trip.  We typically use all quality PENN spinfishing gear on our charters. We can assist novices in casting so no prior experience is required.  The captain will supply all the needed fishing licenses for your excursion.

You can keep anything you catch as long as it's legal to do so.  Capt. Trentin is happy to filet your fish at the end of the trip for you to either take to cook or bring to any of our wonderful local restaurants for them to prepare.

This is a children-friendly charter, though we typically don't recommend children under the age of 6.  Please contact the captain if you have younger kids.

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Customer reviews

Rating summary

4.9/5
out of 5 stars from 118 reviews
Boat
4.8/5
Crew
4.9/5
Experience
4.9/5

Photos & videos by reviewers (92)

Tarpon Fishing Dreams came true!!
Tarpon Fishing Dreams came true!!
Tarpon Fishing Dreams came true!!
+89

Angler rating

107
8
1
1
0

Anglers claimed

Good experience

94%

Appropriate for children

94%

Friendly captain

100%

Satisfied with the boat

99%

Recommend this charter

97%

Caught fish

95%

Showing 1 - 5 of 118 reviews
Showing: 5 of 118 reviews
Dawn K.
Dawn K.
5.0/5

Aug 25, 2025

Evening Tarpon Trip 4PM

Tarpon Fishing Dreams came true!!

VERIFIED

Capt Trentin Leary was the perfect Captain for our trip. He made my son's dreams come true and then some. My husband and I are so happy we found this charter because it was perfect and the sun setting while fishing was absolutely gorgeous. Looking forward to future trips, no doubt!! A captain who has the passion And knowledge needed for my 20 year old twins who are just as passionate about fishing.

Capt Trentin Leary was the perfect Captain for our trip. He made my son's dreams come true and then some. My husband and I are...  

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 Dawn K. recommends Capt. Trentin Leary
 Dawn K. recommends Capt. Trentin Leary

Chad K.
Chad K.
5.0/5

Jul 30, 2025

Seasonal Half Day Trip (PM)

Summer Tarpon trip

VERIFIED

I chose Capt. Trentin simply from his review status and he did not disappoint. We had a wonderful evening tarpon trip. He had plenty of good fresh bait and knew exactly where to put us on the fish. I will definitely re-book with him.if given the chance. Thanks Trentin for the awesome experience.

I chose Capt. Trentin simply from his review status and he did not disappoint. We had a wonderful evening tarpon trip. He had...  

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Review media 1
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 Chad K. recommends Capt. Trentin Leary
1 person finds this review helpful
 Chad K. recommends Capt. Trentin Leary
1 person finds this review helpful

Joe D.
Joe D.
5.0/5

Jan 9, 2025

Seasonal Full Day Trip (7AM)

Great multi species day

VERIFIED

What could have been a tough day after a cold front swept into the ended up being a pleasant day catching multiple species we'd never seen before. It was like fishing in an aquarium. It was the kind of trip I was looking for. Everything we caught doesn't exist back home. We fished every nook cranny and canal to find fish. The Captain apologized that we didn't catch any trophies, but in fact, they all were. Thanks Trentin!

What could have been a tough day after a cold front swept into the ended up being a pleasant day catching multiple species we'd...  

 Joe D. recommends Capt. Trentin Leary
1 person finds this review helpful
 Joe D. recommends Capt. Trentin Leary
1 person finds this review helpful

Nicholas A.
Nicholas A.
5.0/5

Jan 2, 2025

Off Season Half Day Trip (7 AM)

Great Day on the Water with a Great Captain

VERIFIED

Trentin was really knowledgable of the waters and where the fish were hiding. He put us on fish in just a few minutes. Once on the reef Trentin used his experience to help us reel in a 4 foot barracuda which we eventually released. We had a wonderful time and will travel back to Bud N Mary’s to go out with him again.

Trentin was really knowledgable of the waters and where the fish were hiding. He put us on fish in just a few minutes. Once...  

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Review media 1
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 Nicholas A. recommends Capt. Trentin Leary
1 person finds this review helpful
 Nicholas A. recommends Capt. Trentin Leary
1 person finds this review helpful

Jason S.
Jason S.
5.0/5

Jul 15, 2025

Evening Tarpon Trip 4PM

HUGE TARPON

VERIFIED

Captain Trent put us on an absolute giant tarpon. We also caught a huge sting Ray, and a massive Jack. Me and my wife had a great time.

Captain Trent put us on an absolute giant tarpon. We also caught a huge sting Ray, and a massive Jack. Me and my wife had a great...  

 Jason S. recommends Capt. Trentin Leary
 Jason S. recommends Capt. Trentin Leary

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
November 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
Seasonal Half Day Trip (7 AM)
FREE Cancellation 7 days notice
4 Hour Trip, starts at 7:00 AM
Seasonal trip Oct 22 - Nov 30
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US $700 
Entire boat: up to 4 people
Seasonal Half Day Trip (PM)
FREE Cancellation 7 days notice
4 Hour Trip, starts at 11:30 AM
Seasonal trip Oct 22 - Nov 30
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US $700 
Entire boat: up to 4 people
Evening Tarpon Trip 4PM
FREE Cancellation 7 days notice
4 Hour Trip, starts at 4:00 PM
Seasonal trip Jun 1 - Aug 31
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US $700 
Entire boat: up to 4 people
Seasonal 3/4 Day Trip (7 AM)
FREE Cancellation 7 days notice
6 Hour Trip, starts at 7:00 AM
Seasonal trip Oct 22 - Nov 30
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US $900 
Entire boat: up to 4 people
Seasonal 3/4 Day Trip (12 PM)
FREE Cancellation 7 days notice
6 Hour Trip, starts at 12:00 PM
Seasonal trip Jun 1 - Aug 31
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US $900 
Entire boat: up to 4 people
Seasonal Full Day Trip (7AM)
FREE Cancellation 7 days notice
8 Hour Trip, starts at 7:00 AM
Seasonal trip Oct 22 - Nov 30
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US $1,100 
Entire boat: up to 4 people

Customer reviews

Rating summary

4.9/5
out of 5 stars from 118 reviews
Boat
4.8/5
Crew
4.9/5
Experience
4.9/5

Photos & videos by reviewers (92)

Tarpon Fishing Dreams came true!!
Tarpon Fishing Dreams came true!!
Tarpon Fishing Dreams came true!!
+89

Angler rating

107
8
1
1
0

Anglers claimed

Good experience

94%

Appropriate for children

94%

Friendly captain

100%

Satisfied with the boat

99%

Recommend this charter

97%

Caught fish

95%

Showing 1 - 5 of 118 reviews
Showing: 5 of 118 reviews
Dawn K.
Dawn K.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Tarpon Fishing Dreams came true!!

VERIFIED

Evening Tarpon Trip 4PM on August 25, 2025

Capt Trentin Leary was the perfect Captain for our trip. He made my son's dreams come true and then some. My husband and I are so happy we found this charter because it was perfect and the sun setting while fishing was absolutely gorgeous. Looking forward to future trips, no doubt!! A captain who has the passion And knowledge needed for my 20 year old twins who are just as passionate about fishing.

Capt Trentin Leary was the perfect Captain for our trip. He made my son's dreams come true and then some. My husband and I are so happy we found this charter because it was perfect and the sun setting while fishing was absolutely gorgeous. Looking forward to future trips, no doubt!! A captain who has the passion And knowledge needed for my 20 year old twins who are just as passionate about fishing.  

Review media 0
Review media 1
Review media 1
Review media 2
Review media 3
 Dawn K. recommends Capt. Trentin Leary

Chad K.
Chad K.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Summer Tarpon trip

VERIFIED

Seasonal Half Day Trip (PM) on July 30, 2025

I chose Capt. Trentin simply from his review status and he did not disappoint. We had a wonderful evening tarpon trip. He had plenty of good fresh bait and knew exactly where to put us on the fish. I will definitely re-book with him.if given the chance. Thanks Trentin for the awesome experience.

I chose Capt. Trentin simply from his review status and he did not disappoint. We had a wonderful evening tarpon trip. He had plenty of good fresh bait and knew exactly where to put us on the fish. I will definitely re-book with him.if given the chance. Thanks Trentin for the awesome experience.  

Review media 0
Review media 1
Review media 2
Review media 3
Review media 4
Review media 5
 Chad K. recommends Capt. Trentin Leary
1 person finds this review helpful

Joe D.
Joe D.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Great multi species day

VERIFIED

Seasonal Full Day Trip (7AM) on January 9, 2025

What could have been a tough day after a cold front swept into the ended up being a pleasant day catching multiple species we'd never seen before. It was like fishing in an aquarium. It was the kind of trip I was looking for. Everything we caught doesn't exist back home. We fished every nook cranny and canal to find fish. The Captain apologized that we didn't catch any trophies, but in fact, they all were. Thanks Trentin!

What could have been a tough day after a cold front swept into the ended up being a pleasant day catching multiple species we'd never seen before. It was like fishing in an aquarium. It was the kind of trip I was looking for. Everything we caught doesn't exist back home. We fished every nook cranny and canal to find fish. The Captain apologized that we didn't catch any trophies, but in fact, they all were. Thanks Trentin!  

 Joe D. recommends Capt. Trentin Leary
1 person finds this review helpful

Nicholas A.
Nicholas A.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Great Day on the Water with a Great Captain

VERIFIED

Off Season Half Day Trip (7 AM) on January 2, 2025

Trentin was really knowledgable of the waters and where the fish were hiding. He put us on fish in just a few minutes. Once on the reef Trentin used his experience to help us reel in a 4 foot barracuda which we eventually released. We had a wonderful time and will travel back to Bud N Mary’s to go out with him again.

Trentin was really knowledgable of the waters and where the fish were hiding. He put us on fish in just a few minutes. Once on the reef Trentin used his experience to help us reel in a 4 foot barracuda which we eventually released. We had a wonderful time and will travel back to Bud N Mary’s to go out with him again.  

Review media 0
Review media 1
Review media 2
Review media 3
 Nicholas A. recommends Capt. Trentin Leary
1 person finds this review helpful

Jason S.
Jason S.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

HUGE TARPON

VERIFIED

Evening Tarpon Trip 4PM on July 15, 2025

Captain Trent put us on an absolute giant tarpon. We also caught a huge sting Ray, and a massive Jack. Me and my wife had a great time.

Captain Trent put us on an absolute giant tarpon. We also caught a huge sting Ray, and a massive Jack. Me and my wife had a great time.  

 Jason S. recommends Capt. Trentin Leary

FAQs about Capt. Trentin Leary

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Center console boats
Capacity
4 persons
Boat length
22 ft
Year built
1977
Restored in
2024
Boat manufacturer
SeaCraft
Boat type
Bay boat

Engine model
Yamaha
Powered by
1 x 200HP
Max cruising speed
30 knots
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