Southpaw Fishing Charters with Captain Experiences

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A Certified Damn Good Guide is someone who goes above and beyond to show you an incredible experience on your trip. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.

Brad Simonds

Certified Damn Good Guide

Independent Guide 41 years of exp.

Instructional

Quality

Quiet

Comfortable

Intense

Expert Oriented

Captain Brad was born and raised in Massachusetts. After graduating from Princeton University, he moved to the Florida Keys in 1979 to pursue a fishing career. For many years Capt. Brad operated corporately owned sportfishers which were available for charter on the Caribbean fishing circuit. This included winters in the Fl Keys, spring on Mexico’s Yucatan Peninsula, and summer in St. Thomas USVI. Brad also spent 5 fall seasons fishing Venezuela. It's safe to say he knows the Caribbean inside and out!

In 2002 Brad decided to go into business for himself and contracted legendary Key West boat builder Claude Torres for the construction of a 43’ charter boat, which would be home ported in Key West. Seventeen years later Capt. Brad continues to run his daily charter service out of Key West, while also traveling to fish more exotic locales. His 43' vessel remains by common consensus among Key West’s best designed fishing boats.

Now in his 38th year as a charter Captain, Brad has fished from Nova Scotia to South America, and as far afield as Australia. He's...

About Your Guide

Brad Simonds

Certified Damn Good Guide

Independent Guide 41 years of exp.

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Recent Reviews of Southpaw Fishing Charters

5.0

based on 8 reviews

María

Verified Review

We had an amazing time! We had a special interest in Mahi and captain brad and his first mate made it happen. It was great, they made us feel super comfortable and confident. We were able to score Mackerel, Yellowtail and we latched on 3 Mahi’s at the very very last second! Super lucky. Brad and his first mate made it happen! We were able to leave with 2 mackerels and 2 Mahi Mahi’s! Thank...

María

Verified Review

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Karen

Verified Review

Captain Brad and his first mate were amazing. It was my first time fishing off of a boat and I'm glad it was with them! They were both very patient, helpful, and made it an unforgettable experience. We caught snapper and grouper and even hooked an eel! Thanks to both of you for a fantastic time on the water. Highly recommend

Karen

Verified Review

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Johnny

Verified Review

Captain Brad and his deck hand Dennis was awesome given the weather and seas where not very good they still put us on fish and took care of us perfectly. Boat was very nice clean had lots of room (perfect set up) . Would highly recommended Captain Brad !!!!

Johnny

Verified Review

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Shai

Verified Review

We had a fantastic time with captain Brad. We tried different techniques and despite being a rough choppy day we still have out with a lot of fish. We all enjoyed it and highly recommend him to anyone!

Shai

Verified Review

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Jeremiah

Verified Review

Great trip !! Capt and Mate both great boat and equipment well maintained. We landed 2 sails 4 of 5 tuna and a variety of other fish including grouper and snapper.

Jeremiah

Verified Review

Great trip !! Capt and Mate both great boat and equipment well maintained. We landed 2 sails 4 of 5 tuna and a variety of other fish including grouper and snapper.

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Jason

Verified Review

Great time on the water! Very nice boat with plenty of room. Captain and deck hand were great!

Jason

Verified Review

Great time on the water! Very nice boat with plenty of room. Captain and deck hand were great!

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Thomas

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Thomas

Verified Review

Doug, my best friend, and I had a great fishing experience with Captain Brad. Captain Brad and First Mate Jameson are very professional and enjoyable to fish with. The had rigs and bait ready when we arrived. The Southpaw was clean and ready to go. We left on time and had a fantastic "Dawn to Dusk" trip. We started with a quick stop at a buoy to catch some live bait, which was fun. Next we travelled to the first trolling spot. At 8:45 we had a bite on the left outrigger. 45 minutes, and many jumps and runs, later, we had a beautiful blue marlin beside the boat. We have little deep sea fishing experience. The fish was caught on 30 pound test line. Captain Brad and First Mate Jameson did an amazing job ensuring we caught and released the fish. We then continued trolling and around 11 Captain Brad found Mahi Mahi. We made several circles by the weed line they were under and caught 15. We continued trolling and along the way we boated a barracuda and a king mackerel. We did a deep drop and caught some rose fish. We fished a wreck and Doug had something big on the line but could never get it off the bottom. We trolled some more until it was time to return to port.
Captain Brad worked all day long. He never lost focus. He truly loves to do what he does. Jameson was on point all day as well. He is relatively new as a first mate and has learned quickly and always was focused and energetic. Captain Brad has spent a lifetime doing what he does and is still passionate about giving people a great time on the water. He designed his vessel to be a great deep sea fishing vessel, and the Southpaw is. I will recommend Captain Brad to anyone. Fishing is a game of chance. All you can ask for is a captain who is knowledgeable and passionate, a great vessel, and a competent first mate.
We had that experience. Thank you Captain Brad.

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Glenn

Verified Review

Captain Brad had a beautiful well maintained boat. We had a very windy day so difficult to fish the fish were not very active related to the weather but he tried as best he could moved frequently and kept in touch with other captains but no one was having luck that day. His first mate Ryan was very good kept all the fishing poles maintained and gave us helpful instructions....

Glenn

Verified Review

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Potential Target Species

Color-coded seasonality below is based on .

	January	February	March	April	May	June	July	August	September	October	November	December
African Pompano	Great	Great	Good	Good	Good	Good	Good	Good	Good	Good	Great	Great
Amberjack	Good	Good	Good	Good	Great	Great	Great	Great	Great	Good	Good	Good
Black Grouper	Good	Good	Good	Good	Great	Great	Great	Great	Great	Great	Great	Great
Blackfin Tuna	Good	Good	Good	Great	Great	Great	Great	Great	Great	Great	Good	Good
Blue Marlin	Good	Good	Good	Great	Great	Great	Great	Good	Good	Good	Good	Good
Bonito	Good	Good	Good	Good	Great	Great	Great	Great	Good	Good	Good	Good
Cobia	Great	Great	Great	Good	Good	Good	Good	Good	Good	Good	Good	Good
Florida Pompano	Good	Good	Great	Great	Great	Great	Great	Great	Good	Good	Good	Good
Goliath Grouper	Good	Good	Great	Great	Good	Good	Good	Good	Not Ideal	Not Ideal	Good	Good
Hogfish	Good	Good	Good	Great	Great	Great	Good	Good	Good	Good	Good	Good
Kingfish	Great	Great	Great	Good	Good	Good	Good	Good	Good	Good	Good	Great
Mahi Mahi	Good	Good	Good	Great	Great	Great	Great	Great	Great	Great	Good	Good
Mangrove Snapper	Not Ideal	Not Ideal	Not Ideal	Good	Good	Good	Great	Great	Great	Good	Good	Not Ideal
Mutton Snapper	Great	Great	Great	Great	Good	Good	Good	Good	Good	Good	Great	Great
Red Grouper	Good	Good	Good	Good	Great	Great	Great	Great	Great	Great	Great	Great
Red Snapper	Good	Good	Good	Great	Great	Great	Great	Great	Great	Great	Good	Good
Sailfish	Great	Good	Good	Great	Great	Good	Good	Good	Good	Good	Great	Great
Skipjack Tuna	Good	Good	Good	Good	Great	Great	Great	Good	Good	Good	Good	Good
Tilefish	Good	Good	Good	Good	Good	Great	Great	Great	Great	Good	Good	Good
Wahoo	Great	Great	Good	Good	Good	Good	Good	Good	Good	Good	Great	Great
White Marlin	Good	Good	Good	Great	Great	Great	Great	Good	Good	Good	Good	Good
Yellowtail Snapper	Good	Good	Good	Great	Great	Great	Great	Great	Great	Great	Good	Good