Capt. Trentin Leary

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.  We also offer shorter 2 hour trips, however fishing options are much more limited but you can still get out on the water to enjoy Islamorada, and usually catch a few fish.  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 custom restored 22’ SeaCraft center console that can comfortably fish 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, so be aware of that.  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, so you’re welcome to bring your kids for a fun fishing adventure.

Book your trip now and hit the water with Capt. Trentin Leary!



Select date to see available trips and rates:

  • Private trip
    2 Hour Trip (AM)
    FREE Cancellation 7 days notice
    2 Hour Trip, starts at 7:00 AM
    Seasonal trip Nov 1 - Nov 30 (Mon, Tue, Wed, Thu, Fri)
    $350
    The 2 Hour trip is our most inexpensive way to get out on the water. Unfortunately with only two hours you are very limited as to what you can do fishing wise, so we usually book this trip as more of an eco/sight seeing tour. We can try fishing very close to home to catch something, but of course with that time window it can be tough to have a productive fishing experience. But if you just want to get out on the water and enjoy seeing beautiful Islamorada it's a good way to do that.
  • Private trip
    2 Hour Trip (PM)
    FREE Cancellation 7 days notice
    2 Hour Trip, starts at 12:00 PM
    Seasonal trip Nov 8 - Nov 30 (Mon, Tue, Wed, Thu, Fri)
    $350
    The 2 Hour trip is our most inexpensive way to get out on the water. Unfortunately with only two hours you are very limited as to what you can do fishing wise, so we usually book this trip as more of an eco/sight seeing tour. We can try fishing very close to home to catch something, but of course with that time window it can be tough to have a productive fishing experience. But if you just want to get out on the water and enjoy seeing beautiful Islamorada it's a good way to do that.
  • Private trip
    Seasonal Evening Trip (4PM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 4:00 PM
    Seasonal trip Nov 1 - Dec 22
    $600
    Late afternoon/early evening trips are primarily for tarpon. This is a great time to be on the water as it's often less busy with boat traffic and people. Tarpon naturally like to feed right near sunset too so it's a great time to be on the water. Nothing beats hooking up to a silver king as the sun sets in the beautiful Florida Keys! Occasionally we can do other things on an evening trip if there is bait available, but plan on fishing for tarpon unless it's discussed otherwise.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Flats Fishing
    Backcountry Fishing
    Fishing techniques
    Bottom Fishing
    Light Tackle
    Spinning
    Targeted fish
    Tarpon
    Tarpon
  • Private trip
    Seasonal Half Day Trip (12 PM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 12:00 PM
    Seasonal trip Nov 1 - Dec 22
    $600
    This is a 4-hour trip fishing the local waters around Islamorada. We generally do not go much further than about 10 miles from the marina. If you want to catch some Snapper around the islands, fish the shallow patch reefs for various reef fish (Snapper, Grouper, Porgy, etc. – weather permitting), Tarpon around the bridges (mostly spring/summertime), or Mackerel fishing in the local bays, this is a good option.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Flats Fishing
    Backcountry Fishing
    Fishing techniques
    Bottom Fishing
    Light Tackle
    Spinning
    Targeted fish
    Bonefish
    Bonefish
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Shark (Bonnethead)
    Bonnethead Shark
    Shark (Lemon)
    Lemon Shark
  • Private trip
    Seasonal Half Day Trip (7 AM)
    In demand! Last booked: 4 days ago
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 7:00 AM
    Seasonal trip Nov 1 - Dec 22
    $600
    This is a 4-hour trip fishing the local waters around Islamorada. We generally do not go much further than ~10 miles from the marina. If you want to catch some Snappers around the islands, fish the shallow patch reefs for various reef fish (Snapper, Grouper, Porgy, etc.. - and weather permitting), Tarpon around the bridges (mostly spring/summer time), or Mackerel fishing in the local bays, this is a good option.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Flats Fishing
    Backcountry Fishing
    Fishing techniques
    Bottom Fishing
    Light Tackle
    Spinning
    Targeted fish
    Bonefish
    Bonefish
    Jack Crevalle
    Jack Crevalle
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Shark (Bonnethead)
    Bonnethead Shark
    Shark (Lemon)
    Lemon Shark
  • Private trip
    Seasonal 3/4 Day Trip (12 PM)
    FREE Cancellation 7 days notice
    6 Hour Trip, starts at 12:00 PM
    Seasonal trip Oct 1 - Dec 22
    $750
    A 6 hour trip (3/4 day) is basically our extended half day trip. You'll get a couple extra hours to fish over a standard half day trip. During March this often is enough time to try a bit for a trophy tarpon (the silver king!) and if things play out right still have time to catch a few snappers for dinner nearby (dinner & a show!) or try something else. If the tarpon fishing is tougher this also gives you a little extra time compared to a half day to hopefully catch that window where they are biting.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Flats Fishing
    Backcountry Fishing
    Fishing techniques
    Bottom Fishing
    Light Tackle
    Spinning
    Targeted fish
    Bonefish
    Bonefish
    Jack Crevalle
    Jack Crevalle
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Shark (Blacktip)
    Blacktip Shark
    Shark (Bull)
    Bull Shark
  • Private trip
    Seasonal 3/4 Day Trip (7 AM)
    FREE Cancellation 7 days notice
    6 Hour Trip, starts at 7:00 AM
    Seasonal trip Oct 1 - Dec 22
    $750
    A 6 hour trip (3/4 day) is basically our extended half day trip. You'll get a couple extra hours to fish over a standard half day trip. During March this often is enough time to try a bit for a trophy tarpon (the silver king!) and if things play out right still have time to catch a few snappers for dinner nearby (dinner & a show!) or try something else. If the tarpon fishing is tougher this also gives you a little extra time compared to a half day to hopefully catch that window where they are biting.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Flats Fishing
    Backcountry Fishing
    Fishing techniques
    Bottom Fishing
    Light Tackle
    Spinning
    Targeted fish
    Bonefish
    Bonefish
    Jack Crevalle
    Jack Crevalle
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Shark (Blacktip)
    Blacktip Shark
    Shark (Bull)
    Bull Shark
  • Private trip
    Seasonal Full Day Trip (7AM)
    FREE Cancellation 7 days notice
    8 Hour Trip, starts at 7:00 AM
    Seasonal trip Nov 7 - Dec 22
    $900
    A full day of fishing during our busy prime fishing season! March is when the big tarpon start to come in to the Florida Keys and that can be very productive. Still some good opportunities for snook, redfish, bonefish, sharks, and others. Dinner fishing for trout and mangrove snapper is a good bet - of the always popular combo 'dinner & a show' catch your snappers and hook into a large silver king or shark.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Flats Fishing
    Backcountry Fishing
    Fishing techniques
    Bottom Fishing
    Light Tackle
    Spinning
    Targeted fish
    Bonefish
    Bonefish
    Jack Crevalle
    Jack Crevalle
    Permit
    Permit
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Redfish
    Redfish
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Shark (Bull)
    Bull Shark
    Shark (Lemon)
    Lemon Shark
There are 22 people looking at this charter.

FAQs about Capt. Trentin Leary

Capt. Trentin Leary offers the following trips to customers:
  • $350 per group, additional $100 per person after 3 guests - 2 Hour Trip (AM) (2 hours)
  • $350 per group, additional $100 per person after 3 guests - 2 Hour Trip (PM) (2 hours)
  • $600 per group, additional $100 per person after 3 guests - Seasonal Evening Trip (4PM) (4 hours)
  • $600 per group, additional $100 per person after 3 guests - Seasonal Half Day Trip (12 PM) (4 hours)
  • $600 per group, additional $100 per person after 3 guests - Seasonal Half Day Trip (7 AM) (4 hours)
  • $750 per group, additional $100 per person after 3 guests - Seasonal 3/4 Day Trip (12 PM) (6 hours)
  • $750 per group, additional $100 per person after 3 guests - Seasonal 3/4 Day Trip (7 AM) (6 hours)
  • $900 per group, additional $100 per person after 3 guests - Seasonal Full Day Trip (7AM) (8 hours)

When you book a trip with Capt. Trentin Leary, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Live Bait Well
  • Wireless Trolling Motor 36 Volt MinnKota w/ Spot Lock, alternator charger
  • Ice Box

Trips booked with Capt. Trentin Leary include:
  • Rods, reels & tackle
  • Live Bait
  • Lures
  • Catch cleaning & filleting
  • Fishing License (Everglades pass may be needed, which angler buys)

Capt. Trentin Leary offers the following types of fishing:
  • Nearshore Fishing
  • Reef Fishing
  • Flats Fishing
  • Backcountry Fishing

Capt. Trentin Leary offers the following fishing techniques:
  • Light Tackle
  • Bottom Fishing
  • Spinning

Top targeted fish species with Capt. Trentin Leary include:
  • Bonefish
  • Cobia
  • Permit
  • Redfish
  • Shark (Blacktip)
  • Shark (Bull)
  • Shark (Lemon)
  • Snapper (Mangrove)
  • Snook
  • Spanish Mackerel
  • Spanish Mackerel (Narrow-barred)
  • Tarpon

Meet the Charter Operator

Islamorada Fishing Charters and Tarpon Fishing
Islamorada, Florida, United States
34 Fishing Reports
ID & license verified
64 Customer reviews
Response time within an hour
Member since January 2023
Angler's Choice
The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.
Capt. Richard Stanczyk is the owner and operator of Islamorada Fishing Charters and Tarpon Fishing. He has a team of young talented guides who he has been training and who are running trips with him. Capt. Trentin Leary is running his 18’ Action Craft Skiff. He recently got his captain’s license in 2022 and has been fishing offshore as a mate for several years. His love & passion for fishing has pushed him to want to run his own boat which he now has the opportunity. Come book a day with Capt. Trentin to experience all the Florida Keys backcountry has to offer.

About this listing

Targeted species

Bonefish Bonefish
Cobia Cobia
Permit Permit
Redfish Redfish

Boat specs

SeaCraft (Bay boat) originally built in 1977, and restored in 2017. Powered by a 200HP Yamaha engine, with a maximum cruising speed of 30 knots.

Length
22 ft
Capacity
4 persons

Types of fishing

Nearshore Fishing
Reef Fishing
Flats Fishing
Backcountry Fishing

Fishing techniques

Light Tackle
Bottom Fishing
Spinning

Amenities

GPS
Fishfinder
Live Bait Well
Wireless Trolling Motor
36 Volt MinnKota w/ Spot Lock, alternator charger
Ice Box

Trip includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Fishing License
Everglades pass may be needed, which angler buys

Cancellation policy

Free cancellation up to 7 days prior to trip

You can cancel or modify your booking up to 7 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

Listing policies

Pickup agreed upon reservation
Transfer to/from departure site may be available and included in price depending on your location and distance from the dock.
Child Friendly
No Alcohol
Beer OK, no hard liquor
You Keep Catch
Catch and Release Allowed

Payment

Pay online in full

Pay online in full through FishingBooker and save on credit card fees at the dock.

No additional fees.
Book with 25% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 25% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

Cash
Checks

Islamorada fishing calendar

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Recent fishing reports

November Half Day Patch Reef fishing in
November Half Day Patch Reef fishing in
November 20, 2023
Got out on the patches for a trip today. The patches are sets of coral heads, sea fans, and lively hard bottom that are on the atlantic side of the Florida Keys. So not exactly the same as the 'backcountry' gulf side, but it's still fairly shallow 15-30 foot of water. The seacraft boat is great for fishing out here because of it's high gunwales and bow, so you can get out on these bits of reef even when the wind is blowing a little bit. Moreso than you could on a skiff anyways. And the fishing tends to be really good in the fall, winter, and spring when the water is cooler out here. It's a great option on half days you can get good table fare, and pull on a big variety of fish. We had action with barracudas which was fun on light tackle. Also some various groupers on the bottom including a juvenile goliath. A huge nurse shark gave us a good battle as well look how big that sucker is! Hogfish were on the scene too which unfortunately we can't really keep much any longer due to regulations, but they are fun to catch and beautiful to see. And of course a variety of snappers out there too that we were able to get a bucket of for a meal. The phones starting to ring for Christmas week and season next year, and we still have some openings around Thanksgiving.
Continue reading
Great half day with young boy catching s
Great half day with young boy catching s
November 19, 2023
Well a great half day trip today. I had customers book directly. Father and his young 6 year old son. We had beautiful weather with a nice dry north breeze. Caught our live pilchards for bait and hung around some locao bay islands. The juvenile tarpon were happy we hooked several and landed two nice ones. You nornally arent allowed to take tarpon out of the water but these juveniles we can as long as they are under 40 inches and you are careful with them. We also had our nice snappers for action and table fare. We had a half day bookes but we were having such a good time they extended things.
Continue reading
Patch reefs on Fire!
Patch reefs on Fire!
November 7, 2023
Had another awesome half day trip today! We caught pilchards early to start the day, plenty of 'em around as mentioned last report. We hit some shallow water patch reefs on the ocean side with the calmer weather. These are small clusters of coral heads and sea fans on the atlantic side, usually in anywhere from 15 to 30 ft of water. The seacraft I'm running now can get out there even on the slightly rougher days and it is often great fishing this time of year. We had all kinds of action with various snappers, groupers, jacks, and more! We had a few nice jumbo mangrove snappers, and even got a large mutton snapper which was awesome! He got us in the rocks for a few minutes and we let him be, and then maneuvered the boat around and managed to get him loose! We also had quite a few yellow jacks which make for great table fare too.
Continue reading

Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 64 reviews
Boat
Excellent
4.7 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (45)
Great fishing experience
Great fishing experience
3\/4 day inshore. Multiple species. Catch of a lifetime!
+42
Angler rating
56
5
1
1
0
Anglers claimed
Good experience
92%
Friendly captain
100%
Recommend this charter
95%
Appropriate for children
94%
Satisfied with the boat
98%
Caught fish
90%
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Featured  
Showing:
5 of 64 reviews
Brian F.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

It was a good trip.

VERIFIED   NEW  Seasonal Half Day Trip (7 AM) on November 25, 2023
Capt Trenton did a great job with everything. He was knowledgeable and efficient.  I requested that we go after something...
Brian F. recommends Capt. Trentin Leary
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Brian F. recommends Capt. Trentin Leary
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Dan W.
Hazelwood, MO
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

For something different...

VERIFIED   Seasonal Half Day Trip (7 AM) on June 23, 2023
I have been on many charter fishing trips. This was different and fun. I found it interesting taking a few minutes to catch...
Dan W. recommends Capt. Trentin Leary
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Dan W. recommends Capt. Trentin Leary
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Denice B.
Jensen Beach, Florida
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fun filled day with Capt. Trentin

VERIFIED   Seasonal Full Day Trip (7AM) on June 10, 2023
We could not have asked for a better captain for this full day of back country fishing.  He had gone above and beyond to make...
Denice B. recommends Capt. Trentin Leary
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Denice B. recommends Capt. Trentin Leary
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Tim J.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Richard

VERIFIED   Seasonal Half Day Trip (7 AM) on April 14, 2023
Tim J. recommends Capt. Trentin Leary
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Tim J. recommends Capt. Trentin Leary
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Kevin R.
Snyder, NY
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half Day Trip with Captain Trentin

VERIFIED   Half Day Trip (7 AM) on February 12, 2023
Awesome morning on the water with Captain Trentin Leary out of Bud n Mary’s Marina. Texted him the day before and asked if...
Kevin R. recommends Capt. Trentin Leary
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Kevin R. recommends Capt. Trentin Leary
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