Jesse James Charters
Captain

Jesse James Charters

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
4.9
Fishing Experience

What anglers say

97%
Recommend this charter

All reviews (36)

Showing 15 of 36 reviews
  • Gordon Savage
    Gordon Savage
    us
    Wilmington, NC, US
    Member since 2025
    5.0
    Verified

    Outstanding Day of Fishing

    Half Day Trip3 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 Trip2 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 Trip4 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 Trip4 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
    Outstanding Day of Fishing
    Gordon S.
    Gordon S.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    Great captain, boat, and experience
    Joseph G.
    Joseph G.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    First class charter
    Nathan B.
    Nathan B.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    Islamorada mahi success
    Brian B.
    Brian B.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    Black Fin Tuna & Mahi
    Kim F.
    Kim F.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    Fishing with Jack
    Dustin B.
    Dustin B.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    Thoroughly thoughtful
    Jill H.
    Jill H.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    Perfect ending to our Trip
    Brandon H.
    Brandon H.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    June fishing trip
    Daniel K.
    Daniel K.
  • Jesse James Charters
    Jesse James ChartersIslamorada, FL
    Full Day
    Nick L.
    Nick L.

What's biting with Jesse James Charters in Islamorada

The fall is the best time of year to fish the flats in Islamorada, and you'll see this in September. With fewer crowds, lots of Bonefish and Permit on the flats, and Snook in the mangroves, you're in for a treat.

Top catches for September