Southpaw Fishing Charters
Southpaw Fishing Charters
Capt. Brad Simonds owns and operates Southpaw Fishing Charters. He'll take you on exciting fishing trips aboard a 43' custom-built Torres Sportfisher, constructed in 2002 by Claude Torres, a distinguished boat builder. The boat is powered by a 700 HP Lugger diesel engine and comes outfitted with a comprehensive package of navigational and marine electronics. These include a GPS/Chart plotter, multiple fish finders and depth sounders, several VHF radios, and a radar by Northstar and Simrad.
The vessels' two-tiered livewell system enables the crew to maintain large quantities of live bait throughout the trip. Inside the cabin, there's a comfy seating area surrounding a dinette and a spacious cushioned bench.
One of Southpaw's more prominent features is its Tuna tower, which the crew utilizes for a variety of fishing techniques all throughout the year, and which they feel gives them the edge over many of their competitors that don't have a tower on board.
Born and raised in Massachusets, Capt. Brad first started working as a Captain over 30 years ago, running a 55' Holton out of Key Largo, and spending the spring months on the Yucatan Peninsula. After being at the helm of several private and corporate-owned charters, Brad decided to go independent and started the Southpaw Fishing Charters in 2002.
The Southpaw crew specializes in light tackle live bait fishing, trolling, kite fishing, bottom, and wreck fishing for a variety of pelagics and resident game fish inhabiting the area. Those include Billfish, Tuna, Mahi Mahi, Kingfish, Snapper, Grouper and many others.
Custom fishing trips can also be organized upon request, such as bluewater fly fishing, live bait kite fishing, tournament sportfishing, night Snapper or Swordfish trips, as well as fishing excursions to the Tortugas and other long-range trips.
Capt. Brad Simonds owns and operates Southpaw Fishing Charters. He'll take you on exciting fishing trips aboard a 43' custom-built Torres Sportfisher, constructed in 2002 by Claude Torres, a distinguished boat builder. The boat is powered by a 700 HP Lugger diesel engine and comes outfitted with a comprehensive package of navigational and marine electronics. These include a GPS/Chart plotter, multiple fish finders and depth sounders, several VHF radios, and a radar by Northstar and Simrad.
The vessels' two-tiered livewell system enables the crew to maintain large quantities of live bait throughout the trip. Inside the cabin, there's a comfy seating area surrounding a dinette and a spacious cushioned bench.
One of Southpaw's more prominent features is its Tuna tower, which the crew utilizes for a variety of fishing techniques all throughout the year, and which they feel gives them the edge over many of their competitors that don't have a tower on board.
Born and raised in Massachusets, Capt. Brad first started working as a Captain over 30 years ago, running a 55' Holton out of Key Largo, and spending the spring months on the Yucatan Peninsula. After being at the helm of several private and corporate-owned charters, Brad decided to go independent and started the Southpaw Fishing Charters in 2002.
The Southpaw crew specializes in light tackle live bait fishing, trolling, kite fishing, bottom, and wreck fishing for a variety of pelagics and resident game fish inhabiting the area. Those include Billfish, Tuna, Mahi Mahi, Kingfish, Snapper, Grouper and many others.
Custom fishing trips can also be organized upon request, such as bluewater fly fishing, live bait kite fishing, tournament sportfishing, night Snapper or Swordfish trips, as well as fishing excursions to the Tortugas and other long-range trips.
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Customer reviews
Rating
Anglers' gallery (366)
What anglers say
Reviews (286)
Shannon Nelson5.0VerifiedFantastic day
Full Day Trip on August 4, 2026 • 3 adultsI would encourage anyone looking to go out with a family to consider southpaw. The pictures don’t really show it but the boat is set up super nice. My wife appreciated that there was a bathroom and you can sit in the shade at “the kitchen table” and watch the rods or watch your son or anyone else reel in a fish. I don’t really know how else to explain it other than it’s very well thought out. The captain definitely kept us on top of the fish but I can’t say enough about the first mate James. He was amazing. He worked his tail off for us and watched the lines like a hawk. When we did catch a fish he called out fish on and when we had brought it in he got the fish on ice and he had the lines re baited and out in record time. He was truly committed to making sure we got the most of our time. I cannot recommend them enough.
Quinton Bailey5.0VerifiedUnforgettable Experience
3/4 Day Trip on November 13, 2025 • 2 adultsCaptain Brad and James were organized, tactical and hardworking - made for a successful and unforgettable trip. Choppy water but they made us feel very safe. Put us on 3 sailfish and caught plenty of eaters too. Could have brought us back to shore but fished to the last minute hunting down the 3rd sailfish. Sushi at the docks (incredible), filleted our fish, offered pictures, gave restaurant recommendations, gave us the leader of the first sailfish we ever caught - lots of attention to detail that made it excellent. James is incredibly hardworking and patient with all our questions…. Will be coming back!
Sten Gustafson5.0VerifiedCapt. Travis is awesome! Non-stop action
3/4 Day Trip on July 3, 2026 • 4 adultsCapt. Travis is one of the best fishing guides I've ever used (and I've used a lot). Great attitude and demeanor. He asked us what we were looking to catch, and he delivered tremendous fishing action for every kind of fish we were looking for (snapper, grouper, sharks) immediately the moment we pulled up to each spot. My son and nephews had a blast, and were wondering about whether we could come back soon. Highly recommend!
Gene Kittredge5.0VerifiedAnother awesome experience!
Full Day Trip on August 12, 2026 • 3 adultsThis is the second time I booked with Southpaw charter and just as the first time, it did not disappoint. We caught 14 Mahi and a very nice black grouper. Captain Brad and his helper James were very friendly,helpful and patient throughout the trip. They had lots of helpful tips on properly storing and caring for the fish afterwards. I would not hesitate on booking with them.
Deborah CominskiRepeat angler5.0VerifiedOutstanding
3/4 Day Trip on July 6, 2026 • 2 adultsEveryone was complaining that they weren’t catching any fish. Captain Brad and first mate, James did not disappoint. James kept 7 plus lines going effortlessly and we caught seven different kinds of fish from red snapper to Mahi Mahi. Took it to a restaurant and ate it same day and shared it with the restaurant staff. Nothing like it. Melt in your mouth fish! Thanks Captain Brad and James!!
Lawrence Melanson5.0VerifiedGreat Boat. Great Crew.
Half Day Trip on June 6, 2026 • 4 adultsCapt. James and First Mate Jameson were awesome. Boat was clean and organized. Gear was top notch. The fish cooperated. Trolled for Mahi Mahi. At one point, three on at once. Jameson was ready with spinning gear if other fish followed the first one in. Jameson was great with our special needs son. They cleaned, filleted and bagged our catch. Highly recommend Southpaw Fishing.
Abby SmithRepeat angler5.0VerifiedBetter than expected!
3/4 Day Trip on June 3, 2026 • 3 adults • 1 childWe went on this fishing trip with our 9 Yr old son who loves fishing. He said it was better than he thought it would be! Brad and Jameson were awesome! They took the time to answer all of his questions and let him help! We caught a lot of Mahi Mahi! We would definitely recommend this charter to anyone!
Theodore KocakRepeat angler5.0VerifiedSouthpaw Captain Brad Simonds
Half Day Trip on May 7, 2026 • 2 adultsI have fished with Captain Brad when in Key West over the past 20yrs, In my opinion he is best Captain I have ever fished with and we always catch a great variety of fish. We fished May 6th and 7th and have 40lbs of fillets to bring home. Caught a sailfish this trip, snappers, mahi mahi are just some this trip.
Michael Beres5.0VerifiedAttention to Detail
Full Day Trip on January 4, 2026 • 4 adultsCapt. Brad runs a top notch charter. His ship was extremely clean. He goes to great lengths to help you catch what you are looking for. In our case it was sailfish. We had a very successful trip. Also cannot say enough about first mate James. He was on top of line placment and didnt mind answering our children’s questions. I would highly recommend taking your children on Southpaw. We look forward to doing this again!
Chris Scangarello5.0VerifiedWe wanted to get on some mahi mahi.
Half Day Trip - 1:00 PM on July 19, 2026 • 4 adultsCaptain Brad and 1st Mate James were awesome! You could tell they were very knowledgeable and they put us on the mahi. The boat and fishing equipment were all in excellent condition. I highly recommend Southpaw Fishing Charters! Thanks for a great trip!!
Rating
Anglers' gallery (366)
What anglers say
All reviews (286)
I would encourage anyone looking to go out with a family to consider southpaw. The pictures don’t really show it but the boat is set up super nice. My wife appreciated that there was a bathroom and you can sit in the shade at “the kitchen table” and watch the rods or watch your son or anyone else reel in a fish. I don’t really know how else to explain it other than it’s very well thought out. The captain definitely kept us on top of the fish but I can’t say enough about the first mate James. He was amazing. He worked his tail off for us and watched the lines like a hawk. When we did catch a fish he called out fish on and when we had brought it in he got the fish on ice and he had the lines re baited and out in record time. He was truly committed to making sure we got the most of our time. I cannot recommend them enough.
Everything from the Captain, first mate, the boat, the fishing equipment, and all things in-between was fantastic. James, the first mate, was informative and very kind to a number of our first timers. The Captain knew exactly where to go to catch our bait fish and sailfish. About ten minutes in fishing we hooked a sailfish. After about 30ish minutes we landed it. Captain Brad called the day before to confirm everything, provide info about the conditions, and made sure we knew how to find his boat at the marina. We honestly couldn't have asked for a better experience. Highly recommend.
Captain Brad and James were organized, tactical and hardworking - made for a successful and unforgettable trip. Choppy water but they made us feel very safe. Put us on 3 sailfish and caught plenty of eaters too. Could have brought us back to shore but fished to the last minute hunting down the 3rd sailfish. Sushi at the docks (incredible), filleted our fish, offered pictures, gave restaurant recommendations, gave us the leader of the first sailfish we ever caught - lots of attention to detail that made it excellent. James is incredibly hardworking and patient with all our questions…. Will be coming back!
Capt. Travis is one of the best fishing guides I've ever used (and I've used a lot). Great attitude and demeanor. He asked us what we were looking to catch, and he delivered tremendous fishing action for every kind of fish we were looking for (snapper, grouper, sharks) immediately the moment we pulled up to each spot. My son and nephews had a blast, and were wondering about whether we could come back soon. Highly recommend!
This is the second time I booked with Southpaw charter and just as the first time, it did not disappoint. We caught 14 Mahi and a very nice black grouper. Captain Brad and his helper James were very friendly,helpful and patient throughout the trip. They had lots of helpful tips on properly storing and caring for the fish afterwards. I would not hesitate on booking with them.
Thanks Gene, we’ll look forward to your next trip.
FAQs about Southpaw Fishing Charters
- US $1,000 per group - Half Day Trip (4 hours)
- US $1,000 per group - Half Day Trip - 1:00 PM (4 hours)
- US $1,500 per group - 3/4 Day Trip (6 hours)
- US $1,800 per group - Full Day Trip (8 hours)
- US $2,500 per group - Dawn to Dusk (11 hours)
- Toilet Full sized bathroom with electric marine toilet
- Fighting chair
- GPS
- Fishfinder
- Flybridge
- Live bait well
- Outriggers
- Ice box
- Rods, reels & tackle (Penn, Shimano, Daiwa)
- Live bait (In the winter and spring our fishing is almost exclusively live bait fishing. There is no additional charge for live bait. Some days clients are expected to help catch bait.)
- Lures
- Catch cleaning & filleting (We clean and bag your fish free of charge)
- Drinks (Soft drinks & water)
- First mate (15% tip is expected)
- Fishing license (The boat covers fishing licenses for all clients. There is no charge for your license.)
- Fly fishing equipment
- Offshore fishing (Up to 20 miles)
- Reef fishing
- Wreck fishing
- Light tackle
- Heavy tackle
- Bottom fishing
- Trolling
- Spinning
- Jigging
- Fly fishing
- Drift fishing
- Kite fishing
- Deep sea fishing
- Amberjack
- Barracuda (Great)
- Dolphin (Mahi Mahi)
- Grouper (Black)
- King Mackerel (Kingfish)
- Sailfish
- Snapper (Mangrove)
- Snapper (Mutton)
- Snapper (Red)
- Snapper (Yellowtail)
- Tuna (Skipjack)
- Wahoo
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ChecksWhat’s biting in Key West right now
Amberjack
Barracuda (Great)
Dolphin (Mahi Mahi)
Grouper (Black)
King Mackerel (Kingfish)
Sailfish
Snapper (Mangrove)
Snapper (Mutton)
Snapper (Yellowtail)
Tuna (Skipjack)
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