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The "SouthPaw"

Key West Deep Sea Sport Fishing boat with Capt Brad Simonds.

Key West florida deep sea fishing


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Key West Deep Sea Fishing On the "SouthPaw"

Come charter fishing in Key West with award winning Capt. Brad Simonds aboard his 43′ custom charter fishing boat, SOUTHPAW. We offer Key West Fishing charters for up to 6 anglers. Our highly skilled fishing crew is kid friendly and courteous. Capt. Simonds boasts 30 years experience in Florida Keys waters and is an Orvis endorsed guide.

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Capt. Brad Simonds

Troll the blue water of the deep sea or anchor over reefs and wrecks. From Sailfish to Snapper, we offer a wide variety of fishing experiences specializing in live bait and light tackle. Our vessel is clean and well maintained with the biggest fishing cockpit in the fleet. Don’t settle for less, fish the best- SOUTHPAW.

Go With The "SouthPaw" Charters
Key West Deep Sea Sport Fishing

southpaw deep sea

The Charter Boat "SouthPaw"

The SOUTHPAW is a custom 43’ Torres sportfisherman. Constructed in 2002 by renowned Key West boat builder Claude Torres, she incorporates specific design features requested by Capt. Brad which render her an ideal Key West charter fishing platform.

Power aboard the SOUTHPAW is provided by a 700 horsepower Lugger diesel. This power plant is renowned for its dependability and provides a cruising speed of 19 knots which is among the fastest in the fleet. We take the safety of our clients seriously. Our engine room and bilge areas are kept meticulously clean with all bilge pumps and high water alarms in good working order. The most recent marine survey conducted aboard the SOUTHPAW on May 16, 2012 concluded: “The MV SOUTHPAW was found to be in very good to excellent condition overall with signs of continued professional maintenance, upgrades and obvious pride of ownership throughout.”

Charter Details on The "SouthPaw"

We Supply

Ice - Bait - Tournament Rigged Tackle - Licenses

You need to Bring

Food and Drinks - Sunscreen - Hat - Camera - Video Camera - Towels - Polarized Sunglasses

Where are we

Located in the heart of Key West about 5 minutes from anything on the island. When you make reservations we give you easy detailed instructions to get to your boat.


  Private Charters  
8 Hours 6 Hours 4 hours
$1400.00 $1200.00 $900.00
Max 6 passengers

See Our Other Deep Sea Fishing Charter Rates - Key West Fishing Rates

Booking Policies

Booking a fishing charter on this boat requires a deposit of 20% of the total trip fare to secure a day with the balance paid in full at the dock upon your charter date.

There is a 7 day cancellation policy. Cancellations due to bad weather are the captains discretion.

Confirmation of your charter will be sent to you via e-mail after booking. Please make sure your dates are correct before you sign it. Please bring your confirmation with you when you travel.

Call our office to make your reservation on this or any boat in Key West. Our offices are open from 9-5 Mon - Sat. E-mail us for more info -

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The Keys To Key West is a Locally Owned and Operated Company, Members of The Key West Chamber of Commerce.