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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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.
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!

Everyone 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!!
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. 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.
Capt. Brad has 40 years of charter fishing and tournament sportfishing experience. Apart from running a charter business, he's also spent 9 years as a member of the Sanctuary Advisory Council to the Florida Keys National Marine Sanctuary representing the charter boat industry. He welcomes anglers of all skill levels on board – he can help you from teaching basics to a first-timer to providing assistance to a seasoned sea wolf.
Capt. Brad has 40 years of charter fishing and tournament sportfishing experience. Apart from running a charter business, he's also spent 9 years as a member of the Sanctuary Advisory Council to the Florida Keys National Marine Sanctuary representing the charter boat industry. He welcomes anglers of all skill levels on board – he can help you from teaching basics to a first-timer to providing assistance to a seasoned sea wolf.
Free cancellation up to 7 days prior to trip
You can cancel or modify your booking up to 7 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.
Pickup not included
Transfer to/from departure site is not included in trip rates.
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
Visa
Mastercard
Checks
