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Jack Nakashian
Captain

Jack Nakashian

Islamorada, United States
Federal waters
25+ reviews
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

Charter

Rating

4.9
36 reviews
5.0
Boat & Equipment
4.9
Captain & Crew
4.8
Fishing Experience

What anglers say

97%
Recommend this charter

All reviews (36)

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 • 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)
    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 • 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.

    Response from Captain

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

  • Joseph Green
    Joseph Green
    Repeat angler
    us
    Alabama, US
    Member since 2023
    2 trips
    5.0
    Verified

    Great captain, boat, and experience

    3/4 Day Trip • 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)
    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

    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!!

    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 • 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.

    Response from Captain

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

Real catches shared by our community

  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    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!
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    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.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    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.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    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.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    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!
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    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.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    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!
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    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.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    Large platter of prepared fried and grilled fish with lemon wedges, sauces, and salad at a dining table.
    Daniel K.
    Daniel K.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    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's biting with Jesse James Charters in Islamorada

Cobia start to appear, sometimes in big schools. The mullet migration brings Sailfish close to the shore, along with the last of the Blackfin Tuna. This is also a great time for Trout and Redfish in the shallows.

Top catches for November