Southpaw Fishing Key West

Southpaw Fishing Key West

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At Southpaw Fishing Key West, we offer an unparalleled chartered fishing experience. Let us take you Charter fishing in Key West with award winning Capt. Capt.

Brad Simonds aboard his 43′ custom built charter fishing vessel, SOUTHPAW. Key West fishing charters for up to 6 anglers. Highly skilled fishing crew is kid friendly and courteous. Brad Simonds has over 30 years of experience in Florida Keys waters. A multiple time winner of both local and international fishing tournaments as well as an Orvis endorsed guide. Deep Sea Fishing, Bottom Fishing, Wreck

07/29/2026

We had 6 clients, they each kept 5

07/24/2026

Plenty of schoolies around

07/20/2026

Morning 1/2 day.

07/19/2026

A mess of Mangroves

07/08/2026

Stayed on the reef for the morning

06/18/2026

They didn’t want to Dolphin fish all day so we did a bunch of different things.

Photos from Southpaw Fishing Key West's post 06/14/2026

Lots of schoolie Dolphin around the last 10 days.

Photos from Southpaw Fishing Key West's post 05/14/2026

Only had 1 Sailfish bite today, but the meat fish were willing to participate.

Photos from Southpaw Fishing Key West's post 05/11/2026

We’ve caught a couple Sails each of the last several days, also Blackfins up to 24lbs and a few decent Mahi.

05/07/2026

Morning 1/2 day, just the occasional bite from 15-20 lb fish.

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Location

Telephone

Address


5950 Penninsular Avenue
Key West, FL
33040

Opening Hours

Monday 6am - 10pm
Tuesday 6am - 10pm
Wednesday 6am - 10pm
Thursday 6am - 10pm
Friday 6am - 10pm
Saturday 6am - 10pm
Sunday 6am - 10pm