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.
Customer reviews
Rating summary
Photos & videos by reviewers (290)
+287Angler rating
Anglers claimed
Good experience
97%
Appropriate for children
90%
Friendly captain
97%
Satisfied with the boat
100%
Recommend this charter
96%
Caught fish
94%
Jul 13, 2025
Half Day Trip (AM)
An Excellent Experience
Capt. Brad and James were very nice and knowledgeable. They worked hard to put us on top of fish and kept the lines baited the entire time. They gave my family helpful pointers and managed all aspects of the trip to make it memorable and worry free. In the end, we kept 12 mangrove snapper, but caught many more. My son also caught a barracuda which was exciting. A few big mystery fish and a sailfish got away. We would definitely do it again!
Capt. Brad and James were very nice and knowledgeable. They worked hard to put us on top of fish and kept the lines baited the...
Jun 17, 2025
Half Day Trip (AM)
Friendly crew, excellent boat, beautiful views!
The captain and first mate were super friendly and very good at their jobs. The seas were a bit rocky for my liking so we came back a tad earlier than scheduled, but Captain Brad and James were very gracious about it. They put us right on the mahi and we reeled in about 8…5 of which were big enough to keep. The captain offered to clean them for us which we took him up on that. Watching him throw the fish carcasses into the water and see all the tarpon in a frenzy to eat them was entertaining in and of itself. Great experience all around!!!
The captain and first mate were super friendly and very good at their jobs. The seas were a bit rocky for my liking so we came...
Jun 6, 2025
Half Day Trip (AM)
Top-Notch Equipment and Professionalism
Captain Brad & First Mate James did their very best to take us out for Mahi on a 1/2 day AM trip (bit of a tall order on limited time). Though it was a slow day, we did catch 6 Mahi, and 1 was pretty sizable! The boat was immaculately clean and comfortable. Captain Brad cleaned the fish we kept and recommended a local restaurant for lunch. He was also very patient and responsive to my emails/questions prior to booking. We would have loved a bit more conversation from James teaching us about the whys and hows of everything he was doing, but overall a great first-time experience--100% would book again.
Captain Brad & First Mate James did their very best to take us out for Mahi on a 1/2 day AM trip (bit of a tall order on limited...
Jul 3, 2025
3/4 Day Trip
Amazing Experience!
Amazing experience! We’ve gone on several fishing charters and this by far was the best. The first mate, James, was unbelievable with the amount of rods he kept going all the time and it was just two of us. We caught a variety of fish…mahi Mahi (both small and large) which is what you normally catch this time of year, but then we caught blackfin tuna which we’ve wanted to catch for several years now. And to top it all off, we caught a sailfish!
Amazing experience! We’ve gone on several fishing charters and this by far was the best. The first mate, James, was unbelievable...
Dec 28, 2024
3/4 Day Trip
Rough Waters but Great Fishing!
We had a great day with Capt. Brad and First Mate James this past weekend. It was ROUGH getting out to the fishing grounds and anchoring up was a challenge. However, once we got there - we were on the meat! We caught 4 large mutton snapper, 4 kingfish - one of which was more than 20 lbs! Also caught bonita, barracuda and hooked up to a shark. Tons of fun for me and my teen son. I would say that Brad is a serious fisherman so book him if you want to fish - not F around drunk for the day! Brad and James both helped us with our technique and made it so we could reel in a great catch. Totally recommend!
We had a great day with Capt. Brad and First Mate James this past weekend. It was ROUGH getting out to the fishing grounds and...
Captain replied
Trip availability and prices
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Customer reviews
Rating summary
Photos & videos by reviewers (290)
+287Angler rating
Anglers claimed
Good experience
97%
Appropriate for children
90%
Friendly captain
97%
Satisfied with the boat
100%
Recommend this charter
96%
Caught fish
94%
Experience:
Boat
Crew
Overall
An Excellent Experience
Half Day Trip (AM) on July 13, 2025
Capt. Brad and James were very nice and knowledgeable. They worked hard to put us on top of fish and kept the lines baited the entire time. They gave my family helpful pointers and managed all aspects of the trip to make it memorable and worry free. In the end, we kept 12 mangrove snapper, but caught many more. My son also caught a barracuda which was exciting. A few big mystery fish and a sailfish got away. We would definitely do it again!
Capt. Brad and James were very nice and knowledgeable. They worked hard to put us on top of fish and kept the lines baited the entire time. They gave my family helpful pointers and managed all aspects of the trip to make it memorable and worry free. In the end, we kept 12 mangrove snapper, but caught many more. My son also caught a barracuda which was exciting. A few big mystery fish and a sailfish got away. We would definitely do it again!
Experience:
Boat
Crew
Overall
Friendly crew, excellent boat, beautiful views!
Half Day Trip (AM) on June 17, 2025
The captain and first mate were super friendly and very good at their jobs. The seas were a bit rocky for my liking so we came back a tad earlier than scheduled, but Captain Brad and James were very gracious about it. They put us right on the mahi and we reeled in about 8…5 of which were big enough to keep. The captain offered to clean them for us which we took him up on that. Watching him throw the fish carcasses into the water and see all the tarpon in a frenzy to eat them was entertaining in and of itself. Great experience all around!!!
The captain and first mate were super friendly and very good at their jobs. The seas were a bit rocky for my liking so we came back a tad earlier than scheduled, but Captain Brad and James were very gracious about it. They put us right on the mahi and we reeled in about 8…5 of which were big enough to keep. The captain offered to clean them for us which we took him up on that. Watching him throw the fish carcasses into the water and see all the tarpon in a frenzy to eat them was entertaining...
Experience:
Boat
Crew
Overall
Top-Notch Equipment and Professionalism
Half Day Trip (AM) on June 6, 2025
Captain Brad & First Mate James did their very best to take us out for Mahi on a 1/2 day AM trip (bit of a tall order on limited time). Though it was a slow day, we did catch 6 Mahi, and 1 was pretty sizable! The boat was immaculately clean and comfortable. Captain Brad cleaned the fish we kept and recommended a local restaurant for lunch. He was also very patient and responsive to my emails/questions prior to booking. We would have loved a bit more conversation from James teaching us about the whys and hows of everything he was doing, but overall a great first-time experience--100% would book again.
Captain Brad & First Mate James did their very best to take us out for Mahi on a 1/2 day AM trip (bit of a tall order on limited time). Though it was a slow day, we did catch 6 Mahi, and 1 was pretty sizable! The boat was immaculately clean and comfortable. Captain Brad cleaned the fish we kept and recommended a local restaurant for lunch. He was also very patient and responsive to my emails/questions prior to booking. We would have loved a bit more conversation from James teaching us about...
Experience:
Boat
Crew
Overall
Amazing Experience!
3/4 Day Trip on July 3, 2025
Amazing experience! We’ve gone on several fishing charters and this by far was the best. The first mate, James, was unbelievable with the amount of rods he kept going all the time and it was just two of us. We caught a variety of fish…mahi Mahi (both small and large) which is what you normally catch this time of year, but then we caught blackfin tuna which we’ve wanted to catch for several years now. And to top it all off, we caught a sailfish!
Amazing experience! We’ve gone on several fishing charters and this by far was the best. The first mate, James, was unbelievable with the amount of rods he kept going all the time and it was just two of us. We caught a variety of fish…mahi Mahi (both small and large) which is what you normally catch this time of year, but then we caught blackfin tuna which we’ve wanted to catch for several years now. And to top it all off, we caught a sailfish!
Experience:
Boat
Crew
Overall
Rough Waters but Great Fishing!
3/4 Day Trip on December 28, 2024
We had a great day with Capt. Brad and First Mate James this past weekend. It was ROUGH getting out to the fishing grounds and anchoring up was a challenge. However, once we got there - we were on the meat! We caught 4 large mutton snapper, 4 kingfish - one of which was more than 20 lbs! Also caught bonita, barracuda and hooked up to a shark. Tons of fun for me and my teen son. I would say that Brad is a serious fisherman so book him if you want to fish - not F around drunk for the day! Brad and James both helped us with our technique and made it so we could reel in a great catch. Totally recommend!
We had a great day with Capt. Brad and First Mate James this past weekend. It was ROUGH getting out to the fishing grounds and anchoring up was a challenge. However, once we got there - we were on the meat! We caught 4 large mutton snapper, 4 kingfish - one of which was more than 20 lbs! Also caught bonita, barracuda and hooked up to a shark. Tons of fun for me and my teen son. I would say that Brad is a serious fisherman so book him if you want to fish - not F around drunk for the day! Brad...
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