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Jesse James Charters

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Islamorada FL

Guidesly Guarantee

Jack Nakashian, Captain at Jesse James Charters

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Jesse James Charters is the ultimate choice for those seeking a powerful and luxurious fishing experience. With a knowledgeable crew and top-of-the-line equipment, these charters are perfect for both seasoned anglers and novice fishermen looking for a memorable adventure. Captain Jack, your experienced host, and guide, brings over 30 years of expertise to ensure you have the opportunity to catch the fish of your dreams.


The flagship vessel, the Jesse James, is a state-of-the-art Everglades 36' center console boat designed to provide comfort and convenience for up to six anglers of all skill levels. Equipped with ample seating, an electric reel, and expanded live wells for bait and catch storage, this boat takes fishing to a whole new level. Powered by triple 350 HP Yamaha engines, the Jesse James offers a smooth and powerful ride, while also featuring a private toilet for your comfort.


All fishing trips with Jesse James Charters are full-day charters, allowing you to fully immerse yourself in the fishing experience. You have the freedom to choose how far you want to venture and what kind of fish you want to target. Whether you have your sights set on Swordfish or prefer a more versatile fishing experience, such as pursuing Mahi Mahi, Snapper, Tuna, Amberjack, Kingfish, and many other species, the crew will cater to your preferences.


When you book a fishing charter with Jesse James Charters, you can leave all the necessary things needed to the captain. Florida Fishing licenses, fishing equipment, and even the cleaning service for your catch are all taken care of. All you need to bring is your own food, drinks, and sun protection to ensure a comfortable day on the water. It is customary to provide a gratuity tip of 20% to the First Mate who will be accompanying you on the charter.


Jesse James Charters offers more than just a fishing trip; they provide an opportunity to upgrade your fishing skills, catch a trophy-worthy fish that you'll be proud of, and spend quality time with your friends and family. Whether you are seeking a thrilling adventure or a relaxing day on the water, these charters are your ticket to an unforgettable experience.


So, step aboard the Jesse James and get ready for a perfect day of fishing. Let the crew take care of all the details while you focus on making lasting memories. Upgrade your fishing skills, reel in that trophy fish, and enjoy the company of your loved ones. Welcome aboard, book your Islamorada fishing charter today!

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Upcoming Availability

June 2025
July 2025

Expertise & Attributes

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fishing

fishing

Deep Sea FishingDeep Sea FishingDrift FishingDrift FishingGood with FamiliesGood with FamiliesGood with KidsGood with KidsGood with Large GroupsGood with Large GroupsGood with New AnglersGood with New AnglersMaster GuideMaster GuideSaltwater FishingSaltwater Fishing

Fishing Techniques

JiggingTrolling FishingHeavy TackleDeep Sea / Bottom FishingDrift Boat Fishing

What's Included

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Keep your Catch

Keep your Catch

This guide offers trips that you are able to take home your catch.

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Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

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License

License

Read about the licensing details that is / is not covered in the below trips.

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Nature / Wildlife Views

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

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Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

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What's Included

Keep your Catch

Keep your Catch

This guide offers trips that you are able to take home your catch.

Show More

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

Show More

License

License

Read about the licensing details that is / is not covered in the below trips.

Show More

Nature / Wildlife Views

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

Show More

Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

Show More

Trips Available with Jesse James Charters

Experience the Ultimate Fishing Challenge with this Islamorada's Swordfishing Trip!

Fishing

Starting At $2,800

Experience the Ultimate Fishing Challenge with this Islamorada's Swordfishing Trip!

Fishing Area: Islamorada

Fishing: Offshore

Capacity:

Max 6 guests (base trip price includes 6 guests)

Description: Embark on an unforgettable swordfish fishing adventure in Islamorada and make lasting memories! Dive into the deep sea and feel the thrill of reeling in these magnificent creatures. Our experienced fishing charter captain will be by your side, offering assistance whenever you need it. Your Florida fishing licenses and necessary fishing equipment will be taken care of, so you can focus on the excitement. To show appreciation for our First Mate, a 20% gratuity is greatly appreciated. Get ready to create lifelong memories on this exhilarating Islamorada swordfish fishing trip. Book now!

Unleash Your Inner Angler on an Unforgettable Islamorada Fishing Charters!

Fishing

Starting At $1,100

Unleash Your Inner Angler on an Unforgettable Islamorada Fishing Charters!

Fishing Area: Islamorada

Fishing: Offshore

Capacity:

Max 6 guests (base trip price includes 6 guests)

Description: Experience the thrill of nearshore and offshore fishing in Islamorada! Join us on this exciting Florida Keys fishing trip where you can target a variety of species, including Mahi Mahi, Tuna, Grouper, Snapper, and more. We've got you covered with fishing licenses, top-quality fishing equipment, and even cleaning your catch. To show appreciation for our hardworking First Mate, a 20% gratuity is greatly appreciated. Get ready for an unforgettable fishing adventure in the beautiful waters of Islamorada! Book your next fishing charter today with Jesse James Charters!

Vehicle

Jesse James

Boat Type:

Boat Guest Capacity:

6

Boat Length:

36 ft

Manufacturer Name:

Everglades 365

Model Year:

2016

Engine Manufacturer Name:

Yamaha

# of Engines:

3

Horsepower Per Engine:

350

Maximum Cruising Speed:

56

Features: Bait Tank Outriggers Tuna Tubes Toilet Ice-Box Multimedia System Refrigerator Fish Finder GPS Radar

Jesse James Charters Everglades 365 Boat

The Everglades 365 is a sleek center console boat built in 2016. Powered by three 350HP Yamaha engines, it offers a maximum cruising speed of 56 knots.

Boat

Jesse James Charters Everglades 365 Boat image 0

Jesse James

Boat Type:

Boat Guest Capacity:

6

Boat Length:

36 ft

Vehicle Details

FAQs about Jesse James Charters

Ratings & Reviews Summary

5.00
out of 5
Based on 6 ratings
100%
recommended
recommended
Based on 6 recommendations
5
6
4
3
2
1

June 5, 2025

Had a great day fishing with Jesse James Charters and Jack. A great experience started with the drive to the first fishing spot. His boat is very clean and has great equipment and electronics. All fishing rods were ready for our first spot so no time wasted getting ready when we arrived. All we had to do was catch fish. Jack helped us get the fish onto the boat and made sure we were ready to put the line back in the water to catch more fish. A very professional charter and a great captain! Will definitely go out with him again. Check it out if you are planning a fishing trip in the Keys!!

June 5, 2025

Had a great day on the water with Captain Jack and his buddy Tommy. Despite fairly rough seas, they allowed me to operate both offshore and near shore. The boat is top notch fishing equipment with proper rigs and bait!! Highly recommended! !

June 5, 2025

We had a wonderful day on the water! Captain Jack was professional, knowledgeable and his Edgewater boat was great. I highly recommend Jesse James Charters to everyone from experienced anglers to novices.

June 5, 2025

Traveling with Captain Jack will surprise, excite and enrich you. He is very friendly and he is always ready to help.

June 5, 2025

My wife and I had a wonderful time with Captain Jack. We look forward to hosting it again in the near future. I highly recommend you give it a try!!

June 5, 2025

Great captain, great boat, great trip. High winds forced a change in the original plan, but Captain Jack adapted and kept bending the poles throughout the trip.

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