Jesse James Charters 

4.9
(36 reviews)
 
Federally permitted
 101 Buena Vista Court, Islamorada, FL 33036, United States–

Jesse James Charters 

Islamorada, FL, United States
–
36 ft
6
4.9
(36 reviews)

Jesse James Charters offers a powerful luxury ride with a knowledgeable crew, making them equally versatile for both sport fishing and/or family charter for novice anglers. Captain Jack is your host and guide for this adventure. You can count on him to use everything he learned over the past 30 years to help you catch the fish of your dreams.

The Jesse James is a versatile state-of-the-art Everglades 36' center console, comfortably equipped for 6 anglers of All levels. With ample seating, an electric reel, and expanded live wells, for bait and catch, this boat can take the hardcore fisherman to a new level. The boat is powered by triple 350 HP Yamaha engines and features a private toilet as well.

All trips are full day adventures, so you only need to choose how far you want to go and what you want to catch. There's a specialized trip for Swordfish, or you can have versatile targets, and go after Mahi Mahi, Snapper, Tuna, Amberjack, Kingfish, and many more.

The captain covers your fishing licenses, equipment, and catch cleaning service. You only need to pack your food, drinks, and sun protection. A gratuity tip of 20% is advised as the First Mate will be on board with you as well.

Jesse James Charters are your ticket for a perfect day on the water. Upgrade your fishing skills, catch a trophy you'll be proud of, and spend some quality time with your friends and family. Welcome aboard!

Jesse James Charters offers a powerful luxury ride with a knowledgeable crew, making them equally versatile for both sport fishing and/or family charter for novice anglers. Captain Jack is your host and guide for this adventure. You can count on him to use everything he learned over the past 30 years to help you catch the fish of your dreams.

The Jesse James is a versatile state-of-the-art Everglades 36' center console, comfortably equipped for 6 anglers of All levels. With ample seating, an electric reel, and expanded live wells, for bait and catch, this boat can take the hardcore fisherman to a new level. The boat is powered by triple 350 HP Yamaha engines and features a private toilet as well.

All trips are full day adventures, so you only need to choose how far you want to go and what you want to catch. There's a specialized trip for Swordfish, or you can have versatile targets, and go after Mahi Mahi, Snapper, Tuna, Amberjack, Kingfish, and many more.

The captain covers your fishing licenses, equipment, and catch cleaning service. You only need to pack your food, drinks, and sun protection. A gratuity tip of 20% is advised as the First Mate will be on board with you as well.

Jesse James Charters are your ticket for a perfect day on the water. Upgrade your fishing skills, catch a trophy you'll be proud of, and spend some quality time with your friends and family. Welcome aboard!

Jack Nakashian
Captain
Jack Nakashian
ID & credentials verified

Select date to see availability

Trip date:
Group Size:
November 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
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Half Day Trip
FREE Cancellation 3 days notice
4 hour trip starts at 7:00 AM
Dolphin (Mahi Mahi)
Snapper (Red)
Wahoo
Grouper (Black)
US $1,200
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 3 days notice
6 hour trip starts at 7:00 AM
Dolphin (Mahi Mahi)
Snapper (Red)
Wahoo
Grouper (Black)
US $1,500
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 3 days notice
8 hour trip starts at 6:30 AM
US $1,800
Entire boat: up to 6 people
Swordfishing Trip
FREE Cancellation 3 days notice
8 hour trip starts at 6:30 AM
US $2,900
Entire boat: up to 6 people

Customer reviews

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Rating

4.9
36 reviews
5.0
Boat & equipment
4.9
Captain & crew
4.8
Fishing Experience

Anglers' gallery (98)

What anglers say

92%
Recommended

All reviews (36)

Frequently mentioned
Showing 1 – 5 of 36 reviews
Gordon Savage
Gordon Savage
us
North Carolina, US
Member since 2025
5.0
Verified
Outstanding Day of Fishing
Half Day Trip on August 9, 2025 • 3 adults

We had a great day of fishing with Captain Jack. My sons and I booked a last minute trip with Jesse James Charters. Jack was quick to respond and very accommodating for the kind of fishing experience we were looking for. The boat was perfect for our off-shore run on a marginal weather day and Jack had it outfitted for any type of fishing opportunity we came across. We could hear the radio chatter from other boats coming home empty while Jack was able to get us onto some good tuna and mahi fun. If you’re considering some fishing in the Keys, look up Captain Jack at Jesse James Charters!

Reported catch:
Dolphin (Mahi Mahi)
Jack Nakashian
Response from Captain

Thank you guys amazing trip. Can’t wait to see you guys back.

Nathan Bitter
Nathan Bitter
us
Florida, US
Member since 2024
5.0
Verified
First class charter
Half Day Trip on July 27, 2024 • 2 adults

Jesse James charter, with Capt Jack, was awesome. It was evident from the moment we arrived at the dock, that Capt Jack clearly takes pride in his boat and his fishing equipment. The boat was perfectly outfitted, with high quality gear, to ensure the trip had every chance to be successful. The Jesse James was clean, well maintained, and in good working order. All fishing gear was also in good shape, and rigged to go.No time wasted on this charter. Those was my wife’s first time offshore, and also first time dolphin fishing. Capt Jack was an excellent communicator, and quickly taught her the technique to both hook, and land, lots of big dolphin. He struck a great balance of teaching a new fisher (wife) while simultaneously catering to the demands of an experienced angler. No easy feat. Capt Jack went above and beyond to make sure we had a fun, and productive day. We will definitely be using Jesse James charters again, and next time with our kids. Thanks to Capt Jack, our freezer is stocked and we have some excellent new memories.

Jack Nakashian
Response from Captain

Thank you have a great day. Love to see you guys back soon.🎣

Andy Green
Andy Green
Repeat angler
us
Alabama, US
Member since 2023
2 trips
5.0
Verified
Great captain, boat, and experience
3/4 Day Trip on May 30, 2025 • 4 adults

We had a great day with captain Jack catching just over 20 Mahi mahi and then deep dropping to catch a tilefish. He also took extra time on the way back in to let my wife try to catch Mahi with her fly rod. Very accommodating and knowledgeable. We will definitely book Jesse James charter again.

Reported catch:
Dolphin (Mahi Mahi)
Jack Nakashian
Response from Captain

Thanks guys appreciate the review. Can’t wait to see you guys again.

Allen Cox
Allen Cox
Member since 2023
5.0
Great Day Fishing with Captain Jack
3/4 Day Trip on March 29, 2023

Had a great day out fishing with Jesse James Charters with Jack. Awesome experience started with the ride out to our first fishing spot, his boat is very clean and equipped with great gear and electronics. Fishing rods were all set up for our first spot to start fishing so that there was no wasted time getting things ready when we got there. All we had to do was catch fish and Jack assisted to get them in the boat and made sure we were ready to get the lines back in the water to catch more fish. Very professional run charter and a great captain! Will definitely be going back out with him again. If you are planning a fishing trip in the Key's you should definitely look him up!!

Jack Nakashian
Response from Captain
Brandon Heaps
Brandon Heaps
Repeat angler
us
Maryland, US
Member since 2023
2 trips
5.0
Verified
Perfect ending to our Trip
Half Day Trip on August 4, 2023 • 4 adults

Captain Jack was amazing! My wife was nervous about going 20-30 miles off shore, Capt. Jack was compassionate and patient, he talked her through it, gave advice and was a great coach. Capt. Jack was fantastic with my teenage boys, he was a teacher and built confidence. He put us on the fish and we caught enough for dinner for an army. As a boat owner, I was overly impressed with the care he takes in his boat and equipment, everything was in pristine condition. Thanks again Captain Jack, we will be back for sure.

Jack Nakashian
Response from Captain

Pleasure is all mine. Great family. Amazing kids. 🎣👍👍 thank you very much.

FAQs about Jesse James Charters

Jesse James Charters offers the following trips to customers:
  • US $1,200 per group - Half Day Trip (4 hours)
  • US $1,500 per group - 3/4 Day Trip (6 hours)
  • US $1,800 per group - Full Day Trip (8 hours)
  • US $2,900 per group - Swordfishing Trip (8 hours)
When you book a trip with Jesse James Charters, you can expect the following amenities onboard:
  • Toilet
  • GPS
  • Fishfinder
  • Live bait well
  • Refrigerator
  • Multimedia system
  • Outriggers
  • Tuna tubes
  • Ice box
  • Radar
Trips booked with Jesse James Charters include:
  • Rods, reels & tackle
  • Live bait
  • Lures
  • Catch cleaning & filleting
  • First mate (20% gratuity surcharge)
  • Fishing license
Jesse James Charters offers the following types of fishing:
  • Inshore fishing
  • Offshore fishing
  • Reef fishing
  • Wreck fishing
Jesse James Charters offers the following fishing techniques:
  • Light tackle
  • Heavy tackle
  • Bottom fishing
  • Trolling
  • Jigging
  • Drift fishing
  • Deep sea fishing
Top targeted fish species with Jesse James Charters include:
  • Amberjack
  • Dolphin (Mahi Mahi)
  • Grouper (Gag)
  • Grouper (Goliath)
  • Grouper (Snowy)
  • Jack Crevalle
  • King Mackerel (Kingfish)
  • Little Tunny (False Albacore)
  • Snapper (Red)
  • Snapper (Vermilion)
  • Swordfish
  • Tuna (Bluefin)

Your captain

Jack Nakashian
Jack Nakashian
Islamorada, Florida, United States
ID & license verified
36 Customer reviews
Typical response within 6 hours
Member since February 2021
Captain Jack has over 30 years of experience on the Atlantic coastal waters. He likes nothing more than sharing his love of boating and passion for the sport, all making for a memorable day and guaranteed bucket list experience
Jack Nakashian
Jack Nakashian
Fully verified
36
reviews
2021
member since
~6h
response
Captain Jack has over 30 years of experience on the Atlantic coastal waters. He likes nothing more than sharing his love of boating and passion for the sport, all making for a memorable day and guaranteed bucket list experience

The fish you can target

Amberjack
Amberjack
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Gag Grouper
Gag Grouper
Goliath Grouper
Goliath Grouper
Snowy Grouper
Snowy Grouper
Jack Crevalle
Jack Crevalle
King Mackerel (Kingfish)
King Mackerel (Kingfish)
Little Tunny (False Albacore)
Little Tunny (False Albacore)
Red Snapper
Red Snapper
Vermilion Snapper
Vermilion Snapper
Swordfish
Swordfish
Bluefin Tuna
Bluefin Tuna
Amberjack
Amberjack
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Gag Grouper
Gag Grouper
Goliath Grouper
Goliath Grouper
Snowy Grouper
Snowy Grouper

Real catches by this captain

  • Two anglers proudly displaying their catches of Mahi Mahi while fishing on a charter boat in open waters.
    Fish 1
    Fish 2
    Skipjack Tuna
    Gordon S.
    Gordon S.
    We had a great day of fishing with Captain Jack. My sons and I booked a last minute trip with Jesse James Charters. Jack was quick to respond and very accommodating for the kind of fishing experience we were looking for. The boat was perfect for our off-shore run on a marginal weather day and Jack had it outfitted for any type of fishing opportunity we came across. We could hear the radio chatter from other boats coming home empty while Jack was able to get us onto some good tuna and mahi fun. If you’re considering some fishing in the Keys, look up Captain Jack at Jesse James Charters!
  • Three anglers proudly displaying their catch of Mahi Mahi aboard a fishing boat in open waters.
    Fish 1
    Dolphin (Mahi Mahi)
    Joseph G.
    Joseph G.
    We had a great day with captain Jack catching just over 20 Mahi mahi and then deep dropping to catch a tilefish. He also took extra time on the way back in to let my wife try to catch Mahi with her fly rod. Very accommodating and knowledgeable. We will definitely book Jesse James charter again.
  • Two anglers proudly displaying their catch of Mahi Mahi on a sunny day aboard a fishing boat in a tropical setting.
    Fish 1
    Dolphin (Mahi Mahi)
    Nathan B.
    Nathan B.
    Jesse James charter, with Capt Jack, was awesome. It was evident from the moment we arrived at the dock, that Capt Jack clearly takes pride in his boat and his fishing equipment. The boat was perfectly outfitted, with high quality gear, to ensure the trip had every chance to be successful. The Jesse James was clean, well maintained, and in good working order. All fishing gear was also in good shape, and rigged to go.No time wasted on this charter. Those was my wife’s first time offshore, and also first time dolphin fishing. Capt Jack was an excellent communicator, and quickly taught her the technique to both hook, and land, lots of big dolphin. He struck a great balance of teaching a new fisher (wife) while simultaneously catering to the demands of an experienced angler. No easy feat. Capt Jack went above and beyond to make sure we had a fun, and productive day. We will definitely be using Jesse James charters again, and next time with our kids. Thanks to Capt Jack, our freezer is stocked and we have some excellent new memories.
  • Two anglers inside a boat, one adjusting the helm while the other observes the serene ocean view, showcasing a relaxed fishing environment.
    Fish 1
    Dolphin (Mahi Mahi)
    Brian B.
    Brian B.
    Captain Jack of JesseJames Charters is magnificent. He put us on fish and kept us there. The boat is beautiful and well stocked with plenty of rods and tackle. It has full sized toilet. Captain Jack Nakashian knows how to fish various species.
  • Two anglers proudly display a tuna and mahi-mahi aboard a center-console fishing boat offshore.
    Fish 1
    Fish 2
    Blackfin Tuna
    Kim F.
    Kim F.
    We enjoyed our fishing trip with Captain Jack. Caught a few Mahi and a Black Fin Tuna. The boat is very clean and well maintained. Captain Jack spent time teaching us a new fishing technique which was challenging and fun. A great day on the water!
  • An angler proudly displaying a catch of Mahi Mahi and other species on a sunny day at the dock.
    Fish 1
    Dolphin (Mahi Mahi)
    Dustin B.
    Dustin B.
  • Young angler proudly holding a large Snapper while fishing offshore, showcasing a successful day on the water.
    Fish 1
    Fish 2
    Red Snapper
    Jill H.
    Jill H.
    Captain Jack was personable and has a personality to mesh with anyone! He gave instructions that we all could understand. Shared his experiences with us and treated us with the upmost respect and kindness! Exceptional host! Can’t wait to come back down to do more fishing. My 2 teen boys really had a terrific time!
  • Group of anglers holding colorful mahi-mahi beside a neatly arranged catch at a sunny tropical waterfront.
    Fish 1
    Dolphin (Mahi Mahi)
    Brandon H.
    Brandon H.
    Captain Jack was amazing! My wife was nervous about going 20-30 miles off shore, Capt. Jack was compassionate and patient, he talked her through it, gave advice and was a great coach. Capt. Jack was fantastic with my teenage boys, he was a teacher and built confidence. He put us on the fish and we caught enough for dinner for an army. As a boat owner, I was overly impressed with the care he takes in his boat and equipment, everything was in pristine condition. Thanks again Captain Jack, we will be back for sure.
  • Large platter of prepared fried and grilled fish with lemon wedges, sauces, and salad at a dining table.
    Daniel K.
    Daniel K.
  • A young angler and an adult proudly displaying a caught shark aboard a fishing boat, enjoying a sunny day on the water.
    Fish 1
    Fish 2
    Blacktip Shark
    Nick L.
    Nick L.
    Great captain, great boat, great trip. High winds forced us to change our original plans but Capt Jack adjusted and kept the poles bent throughout the trip.

What is the boat like?

Boat image
Boat category
Center console boats
Capacity
6 persons
Boat length
36 ft
Year built
2016
Boat manufacturer
Everglades 365
Boat type
Center console
Engine model
Yamaha F300 4.2L V6
Powered by
3 x 350HP
Max cruising speed
56 knots

What kind of fishing will you do?

Inshore Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Jigging
Drift Fishing
Deep Sea Fishing

Which amenities are available onboard

Toilet
GPS
Fishfinder
Live bait well
Refrigerator
Multimedia system
Outriggers
Tuna tubes
Ice box
Radar
What's included in the trip price
Rods, reels & tackle
Live bait
Lures
Catch cleaning & filleting
First mate
20% gratuity surcharge
Fishing license

How cancellations work

Free cancellation up to 3 days prior to trip
You can cancel or modify your booking up to 3 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.
More details

What the listing policies are

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child friendly
You keep catch
Disabled accessible

How you can pay

Book with 15% deposit, pay rest to captain
When the captain confirms your trip, FishingBooker charges your credit card a 15% 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
 Bank transfer

What’s biting in Islamorada right now

AmberjackAmberjack
Dolphin (Mahi Mahi)Dolphin (Mahi Mahi)
Grouper (Goliath)Grouper (Goliath)
Jack CrevalleJack Crevalle
King Mackerel (Kingfish)King Mackerel (Kingfish)
Snapper (Vermilion)Snapper (Vermilion)
SwordfishSwordfish

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Current
Jesse James Charters
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4 hour trip • 6 persons
US $1,200