Captain Jack’s Fishing Charter’s goal is to create the memory of a lifetime on every trip. Capt. Jack has been fishing the waters of Southwest Florida since he was a toddler and was lucky to have a father and grandfather (who first moved to Fort Myers in 1956) pass on their fishing knowledge to him. All ages and skill levels are welcomed aboard, from rookies to hardcore anglers, Capt. Jack can cater a trip to your needs.

Capt. Jack pilots a beautiful, 2023 Southern Cross 23’ vessel powered by a reliable 2023 Yamaha 225 horsepower motor that can handle rough days and get into shallow fishing holes making it perfect for plying the waters of Southwest Florida. It’s T-top gives plenty of shade from Florida’s brutal sun complete with a tower and second station. An extra-wide beam and clutter-free deck give his clients plenty of room to move around, fight fish and relax. With a brand new trolling motor, massive bait-well, state-of-the-art GPS/SONAR, Bluetooth sound system, and more to help our clients increase their chances of landing fish.

You’ll target a bunch of different fish species, depending on the season and fishing technique you’re using. Some of the most popular catches are Mackerel, Snapper, Redfish, Snook, and Sheepshead. You can keep the catch and the captain will clean it for you after the trip.

Fishing is not the only way to enjoy these waters! Capt. Jack also combines fishing with eco-tours, shelling trips, and sunset cruises. Enjoy the isolated beaches of North Captiva and Cayo Costa State Park, picking up shells the majority can’t reach. Watch beautiful birds, dolphins, and manatees play in their natural habitat instead of an aquarium.

With Captain Jack’s Fishing Charters you simply can’t go wrong!



Select date to see available trips and rates:

  • Private trip
    1/2 Day Eco-Tour/Fishing Trip (AM)
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 8:00 AM
    US $550
    A very family friendly trip! Perfect for groups with children or who want to do more than just fishing. The captain will do whatever makes your party have the best trip possible by fishing for most of the trip or for only a short time. The average trip starts with fishing before switching to sightseeing, shelling, manatee/dolphin watching, swimming, or island hopping. The goal is to provide you with the best day on the water!
    Targeted fish
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    1/2 Day Eco-Tour/Fishing Trip (PM)
    In demand! Last booked: 1 day ago
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 1:00 PM
    US $550
    Depart in the afternoon and start your trip fishing before switching to manatee/dolphin watching, sightseeing, swimming, shelling, or island hopping. Perfect for groups with children or those who want to do more than just fishing. The captain will do whatever makes your party have the best trip possible by fishing for most of the trip or for only a short time. His goal is to provide you with the best day on the water!
    Targeted fish
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    1/2 Day Fishing/Shelling Trip (AM)
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 8:00 AM
    US $550
    Our area is known for two things; our amazing fisheries and beaches full of shells. Take advantage of both in one trip! We can start off fishing inshore for Snook, Redfish, Tripletail, Trout, etc. before switching to shelling. The best way to gather the rarer and more beautiful shells is to take a boat ride to the isolated islands of North Captiva and Cayo Costa. Some parties choose to split-up, with half the group spending time shelling on deserted beaches while the other half fish the nearby waters.
    Targeted fish
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    1/2 Day Fishing/Shelling Trip (PM)
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 1:00 PM
    US $550
    Our area is known for two things; our amazing fisheries and beaches full of shells. Take advantage of both in one trip! We can start off fishing inshore for Snook, Redfish, Tripletail, Trout, etc. before switching to shelling. The best way to gather the rarer and more beautiful shells is to take a boat ride to the isolated islands of North Captiva and Cayo Costa. Some parties choose to split-up, with half the group spending time shelling on deserted beaches while the other half fish the nearby waters.
    Targeted fish
    Jack Crevalle
    Jack Crevalle
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Redfish
    Redfish
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    Half Day Trip – Inshore (AM)
    In demand! Last booked: 4 days ago
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 8:00 AM
    US $550
    On this morning trip, you can target Redfish, Tarpon, Snook, Mangrove Snapper, Spanish Mackerel, Tripletail, Sharks, and more. Let's get on the water and put some fish in the boat! Inshore trips mean visiting fishing holes such as mangrove islands, oyster bars, docks, and passes, while occasionally venturing out into the gulf to fish the beaches.
    Targeted fish
    Jack Crevalle
    Jack Crevalle
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    Half Day Trip – Inshore (PM)
    In demand! Last booked: 1 day ago
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 1:00 PM
    US $550
    Let's get on the water and put some fish in the boat! Inshore trips mean visiting fishing holes such as mangrove islands, oyster bars, docks, and passes, while occasionally venturing out into the gulf to fish the beaches. Catches can include Snook, Spanish Mackerel, Tarpon, Redfish, Seatrout, Mangrove Snapper, Jack, Sharks, and more!
    Targeted fish
    Jack Crevalle
    Jack Crevalle
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    3/4 Day Fishing/Eco-Tour
    FREE Cancellation 1 day notice
    6 Hour Trip, starts at 7:00 AM
    US $750
    A very family friendly trip! Perfect for groups with children or who want to do more than just fishing. We will do whatever makes your party have the best trip possible by fishing for most of the trip or for only a short time. The average trip starts with fishing before switching to sightseeing, shelling, manatee/dolphin watching, swimming, or island hopping. Our goal is to provide you with the best day on the water!
    Targeted fish
    Jack Crevalle
    Jack Crevalle
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    3/4 Day Fishing/Shelling Trip
    FREE Cancellation 1 day notice
    6 Hour Trip, starts at 7:00 AM
    US $750
    Our area is known for two things; our amazing fisheries and beaches full of shells. Take advantage of both in one trip! We can start off fishing inshore for snook, redfish, tripletail, trout, etc. before switching to shelling. The best way to gather the rarer and more beautiful shells is to take a boat ride to the isolated islands of North Captiva and Cayo Costa. Some parties choose to split-up, with half the group spending time shelling on deserted beaches while the other half fish the nearby waters.
    Targeted fish
    Jack Crevalle
    Jack Crevalle
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    3/4 Day Trip – Inshore
    FREE Cancellation 1 day notice
    6 Hour Trip, starts at 7:00 AM
    US $750
    At 6 hours long, a 3/4 day trip offers enough time to do it all! An inshore fishing trip means visiting fishing holes such as mangrove islands, oyster bars, docks, and passes, while occasionally venturing out into the gulf to fish the beaches. Catches can include Snook, Tripletail, Redfish, Seatrout, Tarpon, Mangrove Snapper, Jacks, Spanish Mackerel, Sharks and more!
    Targeted fish
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    Full Day Eco-Tour/Fishing Trip
    FREE Cancellation 1 day notice
    8 Hour Trip, starts at 8:00 AM
    US $950
    A very family friendly trip! Perfect for groups with children or who want to do more than just fishing. We will do whatever makes your party have the best trip possible by fishing for most of the trip or for only a short time. The average trip starts with fishing before switching to sightseeing, shelling, manatee/dolphin watching, swimming, or island hopping. Our goal is to provide you with the best day on the water!
    Targeted fish
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    Full Day Shelling/Fishing Trip
    FREE Cancellation 1 day notice
    8 Hour Trip, starts at 8:00 AM
    US $950
    Our area is known for two things; our amazing fisheries and beaches full of shells. Take advantage of both in one trip! We can start off fishing inshore for Snook, Redfish, Tripletail, Trout, etc. before switching to shelling. The best way to gather the rarer and more beautiful shells is to take a boat ride to the isolated islands of North Captiva and Cayo Costa. Some parties choose to split-up, with half the group spending time shelling on deserted beaches while the other half fish the nearby waters.
    Targeted fish
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
  • Private trip
    Full Day Trip – Inshore
    FREE Cancellation 1 day notice
    8 Hour Trip, starts at 8:00 AM
    US $950
    For the serious anglers that just can't get enough! Let's get on the water and put some fish in the boat! Inshore trips mean visiting fishing holes such as mangrove islands, oyster bars, docks, and passes, while occasionally venturing out into the gulf to fish the beaches. Catches can include Snook, Redfish, Seatrout, Tarpon, Mangrove Snapper, Tripletail, Jacks, Spanish Mackerel, Sharks and more!
    Targeted fish
    Snook
    Snook
    Tarpon
    Tarpon
    Snapper (Mangrove)
    Mangrove Snapper
    Black Drum
    Black Drum
    Redfish
    Redfish
    Grouper (Gag)
    Gag Grouper
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Shark (Blacktip)
    Blacktip Shark
    Tripletail
    Tripletail
    Pompano
    Pompano
    Sheepshead
    Sheepshead
There are 31 people looking at this charter.

FAQs about Captain Jack’s Fishing Charters

Captain Jack’s Fishing Charters offers the following trips to customers:
  • US $500 per group, additional US $50 per person after 3 guests - 1/2 Day Eco-Tour/Fishing Trip (AM) (4 hours)
  • US $500 per group, additional US $50 per person after 3 guests - 1/2 Day Eco-Tour/Fishing Trip (PM) (4 hours)
  • US $500 per group, additional US $50 per person after 3 guests - 1/2 Day Fishing/Shelling Trip (AM) (4 hours)
  • US $500 per group, additional US $50 per person after 3 guests - 1/2 Day Fishing/Shelling Trip (PM) (4 hours)
  • US $500 per group, additional US $50 per person after 3 guests - Half Day Trip – Inshore (AM) (4 hours)
  • US $500 per group, additional US $50 per person after 3 guests - Half Day Trip – Inshore (PM) (4 hours)
  • US $700 per group, additional US $50 per person after 3 guests - 3/4 Day Fishing/Eco-Tour (6 hours)
  • US $700 per group, additional US $50 per person after 3 guests - 3/4 Day Fishing/Shelling Trip (6 hours)
  • US $700 per group, additional US $50 per person after 3 guests - 3/4 Day Trip – Inshore (6 hours)
  • US $900 per group, additional US $50 per person after 3 guests - Full Day Eco-Tour/Fishing Trip (8 hours)
  • US $900 per group, additional US $50 per person after 3 guests - Full Day Shelling/Fishing Trip (8 hours)
  • US $900 per group, additional US $50 per person after 3 guests - Full Day Trip – Inshore (8 hours)

When you book a trip with Captain Jack’s Fishing Charters, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Live Bait Well
  • Multimedia System
  • Wireless Trolling Motor
  • Ice Box

Trips booked with Captain Jack’s Fishing Charters include:
  • Rods, reels & tackle
  • Live Bait (Caught in advance. Baitfish and shrimp.)
  • Lures (Rarely used.)
  • Catch cleaning & filleting (Cleaning, filleting, and bagging fish is included.)
  • Drinks (Water/Gatorade)
  • Fishing License (All licenses are covered in the trip price.)

Captain Jack’s Fishing Charters offers the following types of fishing:
  • Inshore Fishing
  • Nearshore Fishing (When conditions permit.)
  • Flats Fishing
  • Backcountry Fishing

Captain Jack’s Fishing Charters offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Trolling
  • Spinning
  • Deep Sea Fishing

Top targeted fish species with Captain Jack’s Fishing Charters include:
  • Black Drum
  • Grouper (Goliath)
  • Pompano
  • Redfish
  • Shark (Blacktip)
  • Sheepshead
  • Snapper (Mangrove)
  • Snook
  • Spanish Mackerel
  • Spotted Seatrout
  • Tarpon
  • Tripletail

Meet the Captain

Jack Yeslow
Fort Myers, Florida, United States
11 Fishing Reports
ID & license verified
383 Customer reviews
Response time within an hour
Member since October 2019
Let's go out today and make the memory of a lifetime! Fishing is my greatest passion in life, my father and grandfather began fishing our waters in 1956 and instilled an appreciation for this slice of paradise in me. Passing my passion and knowledge onto clients always brings a smile to my face. I hope we get to spend a day on the water together soon!!!

About this listing

Targeted species

Black Drum Black Drum
Grouper (Goliath) Goliath Grouper
Pompano Pompano
Redfish Redfish

Boat specs

Southern Cross (Bay boat) originally built in 2023. Powered by a 225HP Yamaha engine, with a maximum cruising speed of 45 knots.

Length
23 ft
Capacity
6 persons

Types of fishing

Inshore Fishing
Nearshore Fishing
When conditions permit.
Flats Fishing
Backcountry Fishing

Fishing techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Spinning
Deep Sea Fishing

Amenities

GPS
Fishfinder
Live Bait Well
Multimedia System
Wireless Trolling Motor
Ice Box

Trip includes

Rods, reels & tackle
Live Bait
Caught in advance. Baitfish and shrimp.
Lures
Rarely used.
Catch cleaning & filleting
Cleaning, filleting, and bagging fish is included.
Drinks
Water/Gatorade
Fishing License
All licenses are covered in the trip price.

Cancellation policy

Free cancellation up to 1 day prior to trip

You can cancel or modify your booking up to 1 day 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 not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
All ages welcome; life vests provided
You Keep Catch
Captain will clean & bag catch. Regulations apply.
Catch and Release Allowed
Disabled Accessible

Payment

Book with 20% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 20% 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
Visa
Mastercard
American Express
PayPal
Checks
Bank Transfer

Fort Myers Fishing Calendar

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Recent fishing reports

Snook and Seatrout bite is on ???
Snook and Seatrout bite is on ???
March 25, 2024
We’ve been catching a ton of big seatrout out on the flats/sandbars and the snook have moved out of their winter homes and into the creeks/mangrove walls near the rivermouth. We’re getting a few redfish mixed in and small blacktip sharks.
Continue reading
Spring is here!!!
Spring is here!!!
February 29, 2024
These photos are from 2/29/24, the sea trout bite is on fire!!! Great species for kids and those who want to bring home a few meals. We’ve been catching them both with shrimp and live baitfish, fishing sandbars and grassflats with popping corks. The snook have started to really move out of their winter homes. We’ve been catching a good amount of medium sized snook with some slot-sized fish mixed in. Snook season just opened up, it runs for march and april. We’ve been catching a few Redfish mixed-in but not a ton. Lets get out there and bend some rods!!!
Continue reading

Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 383 reviews
Boat
Excellent
4.8 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (349)
Family Friendly-So worth it!
Family Friendly-So worth it!
Family Friendly-So worth it!
+346
Angler rating
342
31
1
5
1
Anglers claimed
Good experience
96%
Friendly captain
99%
Recommend this charter
97%
Appropriate for children
97%
Satisfied with the boat
99%
Caught fish
93%
Sort by:
Featured  
Showing:
5 of 383 reviews
Jamie D.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Family Friendly-So worth it!

VERIFIED   NEW  1/2 Day Eco-Tour/Fishing Trip (AM) on March 25, 2024
This was our first time deep sea fishing and Jack out did himself. First of all, Jack was very patient and understanding with...
Jamie D. recommends Captain Jack’s Fishing Charters
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Jamie D. recommends Captain Jack’s Fishing Charters
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Eric M. L.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Lots of action!

VERIFIED   Half Day Trip – Inshore (PM) on February 19, 2024
We scheduled a 4 man trip the evening prior to the afternoon of our desired charter.  Captain Jack quickly confirmed the trip,...
Eric M. L. recommends Captain Jack’s Fishing Charters
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Eric M. L. recommends Captain Jack’s Fishing Charters
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Brandon J.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Family 1st Charter

VERIFIED   3/4 Day Fishing/Eco-Tour on November 22, 2023
This was our first charter trip so nothing to really compare the trip to, but we had an amazing time.  We had our 10 year...
Brandon J. recommends Captain Jack’s Fishing Charters
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Brandon J. recommends Captain Jack’s Fishing Charters
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Kevin F.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

We’ll be back!

VERIFIED   NEW  Half Day Trip – Inshore (AM) on March 15, 2024
Thanks Captain Jack…the boys had a great time and we’ll see you next spring break!  My youngest had certain fish he wanted...
Kevin F. recommends Captain Jack’s Fishing Charters
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Kevin F. recommends Captain Jack’s Fishing Charters
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You found this review helpful

Alan R.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fun trip

VERIFIED   NEW  Half Day Trip – Inshore (AM) on March 11, 2024
Captain took good care of us, worked hard to keep us fishing. We had new fishermen on board and got lines tangled a couple...
Alan R. recommends Captain Jack’s Fishing Charters
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Alan R. recommends Captain Jack’s Fishing Charters
Mark review as helpful
You found this review helpful