Southpaw Fishing Charters - Key West

Starting at $800

Pricing & Availability

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Fishing Info


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

Water Type


Skill Level

Beginner, Intermediate, Advanced


Amberjack, Bonito, Cobia, Mahi Mahi / Dorado, Black Grouper, Goliath Grouper, Red Grouper, Hogfish, African Pompano, King Mackerel / Kingfish, Florida Pompano, Sailfish, Mangrove Snapper, Mutton Snapper, Red Snapper, Yellowtail Snapper, Tilefish, Blackfin Tuna, Skipjack Tuna, Wahoo

About Your Trip

Join Captain Brad Simonds of Southpaw Fishing Charters 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.

Southpaw Fishing Charters 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!

About Your Boat

Boat type: Sportfisher

Boat Manufacturer: Torres

Boat length: 43ft

Engine Manufacturer: Lugger

Engine HP: 700HP

Number of engines: 1

Extras: Fighting Chair, GPS, Fishfinder, Flybridge, Live Bait Well, Outriggers, Ice Box


Tom H.

June 13, 2020

Captain Brad and Mick were first class. The boat and equipment were impeccably kept. Their attention to detail was noticed and appreciated. Mick was the hardest working mate I’ve ever been around. We did two trips with them. The first was a 4-Hour reef trip where I brought my three sons and two of their girlfriends for the afternoon. We caught a nice variety of fish and everyone had a great time. The second trip was an 8-hour offshore on Saturday for me and my three sons. We had a great day. We again caught a nice amount of Mahi, Tuna and my youngest son even caught a Sailfish! It was a day I will never forget as a father and when I get back to Key West, The Southpaw will be our boat!

Jonathan S.

September 18, 2020

Capt. Brad and his mate Mick were excellent. The September bite off key west for Mahi isn’t the best but they got us on the fish and we had a great time. Multiple double, triple and even a few quad headers in that short span. Tossed a few back due to size but had a great time regardless. Would 100% recommend using this boat and crew. Boat is newer and in excellent shape, plenty of room and nice and wide open for everyone to fish at the same time.

Scott S.

September 17, 2020

My wife and I had a great time fishing with Capt. Brad and 1st mate Mick. The fishing wasn’t spectacular but we still ended up landing 8 tunas and a whole mess of Mahi! When we had a fish on Mick was on it, he did a great job and really knew his stuff. The boat was spotless, well maintained, very roomy, and plenty of shade to get out of the blazing sun when the fish weren’t biting. Highly recommend.



All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.


Feel free to enjoy responsibly, but please no glass.

Boat Restroom


Live Bait

Yes, Included


You will get a refund if the trip is canceled due to weather.


No meal provided.

Gear & Packing


Rods, reels, tackle

At an Additional Rate

No added costs.

Recommended Packing

Hat, sunscreen, polarized sunglasses, foods, and drinks

Required Items

A valid fishing license.

Things to Keep in Mind

Payment & Tipping

After paying the deposit, a QR Code will be emailed to you. On the day of the trip, your guide will scan your QR code to automatically transfer the remaining balance. The only cash needed is for a customary tip (we recommend 20%).

Cancellation/Refund Policy

Yes, cancel for free up to 7 days before the trip.

Where to Buy a Fishing License

Find a license for your state here.


Start Location

Oceans Edge Resort & Marina Key West, 5950 Peninsular Ave, Key West, FL 33040, United States

Start Time(s)

07:00 AM, 08:00 AM, 01:00 PM


4 hours, 6 hours, 8 hours,