Southpaw Fishing Key West

Southpaw Fishing Key West 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

Fishing, Kite Fishing, Live Bait Fishing, Light Tackle Fishing

Our vessel is clean and well maintained with the biggest fishing cockpit in the fleet. Don’t settle for less, fish the best- SOUTHPAW.

Late August Mahi. The one in the middle weighed 20 lbs.
08/30/2026

Late August Mahi. The one in the middle weighed 20 lbs.

Mahi’s and a Sail
08/11/2026

Mahi’s and a Sail

Found a few
08/06/2026

Found a few

We had 6 clients, they each kept 5
07/29/2026

We had 6 clients, they each kept 5

Plenty of schoolies around
07/24/2026

Plenty of schoolies around

Morning 1/2 day.
07/20/2026

Morning 1/2 day.

A mess of Mangroves
07/19/2026

A mess of Mangroves

Stayed on the reef for the morning
07/08/2026

Stayed on the reef for the morning

They didn’t want to Dolphin fish all day so we did a bunch of different things.
06/18/2026

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

Lots of schoolie Dolphin around the last 10 days.
06/14/2026

Lots of schoolie Dolphin around the last 10 days.

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

Telephone

+13053932306

Website

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