Southpaw Fishing Charters in Key West, Florida

Guided by Brad Simonds

Deep Sea Nearshore

About Your Guide

41 Years of Experience
Profile photo of Captain Experiences guide Brad

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 gone just about everywhere and fished for just about everything, but to him, the Keys are home.

Southpaw Fishing Charters Trips

Join Captain Brad on an exciting fishing adventure in Key West, Florida. Captain Brad is extremely friendly and courteous, and wants to help you reel in your personal best! On these 4, 6, and 8-hour adventures, Captain Brad will help you catch a variety of species, including Mahi Mahi / Dorado, Black Grouper, Goliath Grouper, Red Grouper, King Mackerel / Kingfish, Sailfish, Red Snapper (depending on the season), Yellowtail Snapper, and Wahoo. You’ll be fishing aboard Capt. Brad’s 43-foot sportfisher which is equipped with a large fishing cockpit, a functioning Tuna Tower, and an extra-large live well capacity. On this trip, Captain Brad emphasizes light tackle but is more than happy to accommodate for live bait slow trolling, reef & wreck, dead bait trolling, kite fishing, and blue water fly fishing. Captain Brad will provide Penn, Shimano, and Daiwa rods, reels, tackle, and lures. They will also provide live bait, drinks, fly fishing equipment, and fish cleaning/filleting at no extra cost. A first mate will be on board to help you at all times. Make sure you bring a hat, sunscreen, and some food/snacks for the day! The crew is excited to give you a great fishing trip – it doesn’t matter if you’ve fished a hundred times or whether this is your first time taking the family fishing – there’s something for everyone to enjoy! Read More

Deep Sea, Nearshore Fishing Charter in Key West

Key West Mixed Bag Trip

100% (2)
43 ft 1 - 6 People From $142 / person

Join Captain Brad on an exciting all-day fishing adventure in Key West, Florida. Captain Brad is extremely friendly and courteous, and wants to help you reel in your personal best! On this 11-hour adventure, Captain Brad will help you catch some trophy-sized fish, including Dorado (Mahi Mahi), Blue Marlin, Red Snapper, Striped Marlin, White Marlin, and Sailfish. You’ll want to stretch out before this trip - some of these guys will put up one hell of a fight! You’ll be fishing aboard Capt. Brad’s 43-foot sportfisher which is equipped with a large fishing cockpit, a functioning Tuna Tower, and an extra-large live well capacity. On this trip, Captain Brad emphasizes light tackle but is more than happy to accommodate for live bait slow trolling, reef & wreck, dead bait trolling, kite fishing, and blue water fly fishing. Captain Brad will provide Penn, Shimano, and Daiwa rods, reels, tackle, and lures. They will also provide live bait, drinks, fly fishing equipment, and fish cleaning/filleting at no extra cost. A first mate will be on board to help you at all times. Make sure you bring a hat, sunscreen, and some food/snacks for the day! Test your skills and strength and fill the boat on what promises to be an exhilarating day with Captain Brad and his crew! Read More

Deep Sea Fishing Charter in Key West

Dawn To Dusk Key West Fishing Trip

100% (2)
43 ft 1 - 6 People From $333 / person

Recent Reviews of Southpaw Fishing Charters

Jeremiah

Verified Review Fishing

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.

Jason

Verified Review Fishing

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

Thomas

Verified Review Fishing

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.

Glenn

Verified Review Fishing

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. He kept moving the whole 8 hr trip. Hopefully next time fishing conditions will be better.

Species

African Pompano, Amberjack, Black Grouper, Blackfin Tuna, Blue Marlin, Bonito, Cobia, Florida Pompano, Goliath Grouper, Hogfish, Kingfish, Mahi Mahi, Mangrove Snapper, Mutton Snapper, Red Grouper, Red Snapper, Sailfish, Skipjack Tuna, Striped Marlin, Tilefish, Wahoo, White Marlin, Yellowtail Snapper

Techniques

Bottom Fishing, Heavy Tackle Fishing, Jigging, Kite Fishing, Light Tackle Fishing, Trolling

Types of Fishing

Deep Sea, Nearshore

Start Location

Oceans Edge Resort & Marina Key West, 5950 Peninsular Ave, Key West, FL 33040, United States | Bodies of water fished: Florida Keys, Big Pine Key, Cudjoe Key, Summerland Key, Key West

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