Key West Fishing Charters

Enjoy your Key West fishing charters with award winning Capt. Brad Simonds aboard his premier charter boat, the 43′ custom built charter fishing vessel, SOUTHPAW.  We offer fishing charters for up to 6 anglers.  Our highly skilled fishing crew is kid friendly and courteous.  Capt. Brad Simonds has 38 years of experience in the Florida Keys water and a reputation for excellence.  Your captain is a multiple time winner of both local and international fishing tournaments as well as an Orvis endorsed guide.

Southpaw Fishing offers the best deep sea fishing in Key West as well as, bottom fishing, wreck fishing, kite fishing, live bait fishing, and light tackle fishing.

Our custom built charter boat SOUTHPAW is clean and well maintained with Key West’s best designed fishing layout.  Our boat is quite literally the envy of the fleet.  Why settle for less?  Fish with the best Key West fishing charters, Southpaw Fishing.

Couple posing with fresh caught mahi mahi


  • The largest fishing cockpit
  • A functioning Tuna Tower
  • Extra-large live well capacity
  • Clean well maintained and uncluttered
Woman holding a nice black grouper

Fishing Techniques

  • Emphasis on light tackle
  • Live bait slow trolling
  • Reef & wreck
  • Kite fishing
  • Blue water fly fishing
  • Dead bait trolling


Our Clients Say

Fish Avatar

“We really enjoyed our recent fishing trip with you, you do a great job of making all of the group comfortable, and fully involved…Your new boat is great, very comfortable and very conducive to great fishing–I’m looking forward to fishing with you many more times. Tight lines and screaming reels.”

Jim Toabe – 30 year client
Fish Avatar

“Accommodating us with trolling and shallow water was great in itself let alone taking the extra time to try for the Cobias. My mother-in-law and the rest of the group are still talking about it. Hooking my first billfish was awesome and a double header with my wife made it that [much] more special. Like I told you before, whenever I get the chance to fish out of Key West, you will be my first call and I’ll recommend you to anyone I know going down there.”

Steven Dean – first time client
Fish Avatar

“Just wanted to drop you guys a line and thank you again for a great day out on the water. You guys totally surpassed my expectations. I was a little nervous about how the day was going to go and what we would catch being the cost of a 3/4 day trip, but I would not hesitate to do it again every time I’m in Key West. You and Heath are a real class act and make a great team and will book again in the future. Thanks!”

Tyler Randell—first time client
Fish Avatar

“Just a quick note to let you all know that we had a great outing. I was on Southpaw with Captain Brad & 1st mate Heath. Not only were these guys friendly & jovial but their professionalism was clearly evident in the level of preparedness of tackle, bait & boat! All day long they put forth the effort to make sure we had a great time and to give us every opportunity to catch fish. I’ve been on enough charters with other outfits to know that Team Southpaw ranks at the high end of high!”

Russ - first time client

Latest Key West Fishing Reports

July 2, 2019

July 2nd, 2019|

Dolphin fishing has been our primary focus over the last month. This is typical for this time of year. Most of the action has taken place well offshore from the edge of the wall where

May 28, 2019

May 28th, 2019|

Over the past month we have seen a steady improvement in the fishing. A distinct color change has been in place for three week, featuring green water on one side and bright blue water with

April 30, 2019

May 1st, 2019|

Fishing over the last month has been challenging. We have had an on going issue with scattered Sargasso weed which has been so thick it is often impossible to fish a given area. Water quality

Book Online