Jesse James Charters with Captain Experiences

About Your Guide

Jack Nakashian

Independent Guide

Quiet

Intense

Instructional

Beginner Oriented

Adventurous

Quality

Captain Jack and his experienced friendly Jesse James crew welcome you aboard for a great day on the water in beautiful Islamorada, also known as the Fishing Capital of the World.
Jesse James is a versatile state of the art Everglades 365 vessel comfortably equipped for 6 anglers at all levels. With ample seating, electric reel and expanded live wells, for bait and catch, we can take the hard-core fisherman to a new level. We excel in hands on guidance and instruction to catch Mahi, Wahoo, Sailfish, Tuna, as well as deeper drop (300ft to 600ft) for Vermillion Snapper and Snowy Grouper, as well as, other deep water fish species. Every deep water outing brings the possibility of wrangling a SWORD Fish, Marlin, Sharks, Cobia or other Sport Fish. We are committed to making your Sport Fishing trip as productive as possible, taking into account that adverse weather and No fish in area can limit catch quantity. We troll the Reef and Gulf Stream for the best fishing opportunities each day to target your personalized outing. Jesse James is a...

About Your Guide

Jack Nakashian

Independent Guide

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Islamorada Fishing Adventure

NEW Islamorada, FL 1 - 6 People 4 - 8 Hours From $1,100

Reserve Your Trip

Islamorada Fishing Adventure

Deep Sea, Nearshore Fishing in Islamorada

NEW Guided by Jack

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Book your trip with confidence — We only work with the best local guides that know where to put you on fish.

Pricing Matrix

	8 Hours	6 Hours	4 Hours
1 Person	$1,100.00	$1,400.00	$1,700.00
2 People	$1,100.00	$1,400.00	$1,700.00
3 People	$1,100.00	$1,400.00	$1,700.00
4 People	$1,100.00	$1,400.00	$1,700.00
5 People	$1,100.00	$1,400.00	$1,700.00
6 People	$1,100.00	$1,400.00	$1,700.00

Pay 15% of the price as a deposit today, with the balance due on the day of the trip.

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Browse Similar Trips

About Your Trip

Water Type

Deep Sea, Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather

About Your Trip

Are you ready for your next fishing adventure? Captain Jack and his experienced crew are here to offer a luxurious, fun-filled day on the water, perfect for both passionate anglers and families looking to create lasting memories. With over 30 years of expertise, Captain Jack knows exactly how to guide you toward the catch of your dreams, whether you’re a seasoned pro or just starting out.

Step aboard the 36’ Everglades center console, a state-of-the-art vessel designed for up to six anglers of all skill levels. Powered by triple 350 HP Yamaha engines, this boat is built for both comfort and performance. It features ample seating, an electric reel, expanded live wells, and even a private toilet to ensure a smooth and enjoyable ride. Modern technology such as GPS, radar, fishfinders, and outriggers adds to the excitement, making your trip both productive and thrilling.

Each trip with Captain Jack is a full-day adventure, allowing you the time and flexibility to tailor your experience to your goals. Whether you choose a half-day, 3/4 day, or full-day trip, the possibilities are endless. Target popular species like Mahi Mahi, Red Snapper, Wahoo, and Black Grouper, or go offshore to chase Tuna, Amberjack, and Kingfish. The adventure is yours to shape.

The boat is equipped with all the amenities you need for an incredible day, including a live bait well, tuna tubes, refrigerator, multimedia system, and ice box to keep your catch fresh. Captain Jack takes care of the details, providing fishing licenses, rods, reels, tackle, live bait, and lures, as well as cleaning and filleting your catch so it’s ready to take home. All you need to bring is food, drinks, sun protection, and plenty of enthusiasm. A 20% gratuity for the hardworking First Mate is recommended to show your appreciation.

This is more than just a fishing trip—it’s your chance to level up your skills, catch a trophy fish, and spend quality time with your loved ones. Whether you’re drawn to inshore, offshore, reef, or wreck fishing, Captain Jack and his team are ready to create an experience you’ll never forget. Book your trip today and get ready for the adventure. Welcome aboard!

Amenities

Water Type

Deep Sea, Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Boat Restroom

This boat has a restroom.

Live Bait

Live bait is included for this trip.

Weather

You won’t lose your deposit if the trip is canceled due to weather

Flexible Cancelation

This trip can be canceled for a refund up to 3 days before the trip.

Beer

No beer allowed.

Kid Friendly

This trip is best for adults.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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About Your Boat

Boat photo for Islamorada Fishing Adventure

Boat Type: Center Console
Boat Manufacturer: Everglades 365
Year Built: 2016
Boat Length: 36'

About Your Boat

Boat Type: Center Console
Boat Manufacturer: Everglades 365
Year Built: 2016
Boat Length: 36'
Engine Manufacturer: Yamaha F300 4.2L V6
Total Horsepower: 1050
Number of Engines: 3
Additional Amenities: GPS, Fishfinder, Live Bait Well, Refrigerator, Multimedia System, Outriggers, Tuna Tubes, Ice Box, Radar

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Potential Target Species

Color-coded seasonality below is based on .

	January	February	March	April	May	June	July	August	September	October	November	December
Amberjack	Good	Good	Good	Good	Great	Great	Great	Great	Great	Good	Good	Good
Black Grouper	Good	Good	Good	Good	Great	Great	Great	Great	Great	Great	Great	Great
Bluefin Tuna	Not Ideal	Not Ideal	Good	Good	Great	Great	Great	Good	Good	Good	Good	Not Ideal
False Albacore	Not Ideal	Not Ideal	Not Ideal	Good	Great	Great	Great	Good	Good	Good	Not Ideal	Not Ideal
Gag Grouper	Good	Good	Good	Great	Great	Great	Great	Good	Good	Good	Good	Good
Goliath Grouper	Good	Good	Great	Great	Good	Good	Good	Good	Not Ideal	Not Ideal	Good	Good
Jack Crevalle	Good	Good	Good	Good	Great	Great	Great	Great	Good	Good	Good	Good
Kingfish	Great	Great	Great	Good	Good	Good	Good	Good	Good	Good	Good	Great
Mahi Mahi	Good	Good	Good	Great	Great	Great	Great	Great	Great	Great	Good	Good
Red Snapper	Good	Good	Good	Great	Great	Great	Great	Great	Great	Great	Good	Good
Snowy Grouper	Good	Good	Good	Great	Great	Great	Good	Good	Good	Great	Good	Good
Vermillion Snapper	Good	Good	Good	Good	Good	Good	Good	Good	Good	Good	Good	Good
Wahoo	Great	Great	Good	Good	Good	Good	Good	Good	Good	Good	Great	Great