Southpaw Fishing Charters

5950 Peninsular Ave
Key West FL, United States

Capt. Brad Simonds owns and operates Southpaw Fishing Charters, a 43’ custom-built Torres Sportfisher, constructed in 2002 by Claude Torres, a distinguished boat builder. The boat is powered by a 700HP Lugger diesel engine, and comes outfitted with a comprehensive package of navigational and marine electronics, which includes a GPS/Chart plotter, multiple fish finders and depth sounders, several VHF radios and a radar by Northstar and Simrad.

The vessels’ two-tiered livewell system enables the crew to maintain large quantities of live bait throughout the trip. Inside the cabin, there’s a comfy seating area surrounding a dinette and a spacious cushioned bench. One of Southpaw’s more prominent features is its Tuna tower, which the crew utilizes for a variety of fishing techniques all throughout the year, and which they feel gives them the edge over many of their competitors that don’t have a tower on board.

Born and raised in Massachusets, Capt. Brad first started working as a Captain over 30 years ago, running a 55’ Holton out of Key Largo, and spending the spring months on the Yucatan Peninsula. After being at the helm of several private and corporate-owned charters, Brad decided to go independent and started the Southpaw Fishing Charters in 2002.

The Southpaw crew specializes in light tackle live bait fishing, trolling, kite fishing, bottom and wreck fishing for a variety of pelagics and resident game fish inhabiting the area, including Billfish, Tuna, Dorado, Kingfish, Snapper, Grouper and many others. Custom fishing charters can also be organized upon request, such as bluewater fly fishing, live bait kite fishing, tournament sportfishing, night Snapper or Swordfish trips, as well as fishing excursions to the Tortugas and other long range trips.

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About this listing

Boat Specs

Torres (Convertible) originally built in 2002. Powered by 700HP Lugger engine, with a maximum cruising speed of 19 knots.

43 ft
6 persons
Types of Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing
Fishing Techniques
Light Tackle
Heavy Tackle
Bottom Fishing
Fly Fishing
Drift Fishing
Kite Fishing
Targeted Species
Barracuda (Great)

Dolphin (Mahi Mahi)
Grouper (Black)

King Mackerel (Kingfish)

Snapper (Mangrove)
Snapper (Mutton)

Snapper (Red)
Snapper (Yellowtail)

Tuna (Skipjack)
Air Conditioning
Fighting Chair
Life Jackets
Fly Fishing Equipment
Snorkeling Equipment
Live Bait Well
Multimedia System
Wireless Trolling Motor
Tuna Tubes
Spearfishing Equipment
Ice Box
Fighting Chair
Life Jackets
Trip Includes
Rods, reels & tackle
Penn, Shimano, Daiwa
Live Bait
Catch cleaning & filleting
Soft drinks & water
First Mate
Fishing License
Fly Fishing Equipment
FREE Cancellation
You can cancel or change your booking free of charge up to 7 days before the trip date.
Pickup not included
Transfer to/from departure site is not included in trip rates.

Other Policies  
Child Friendly
You Keep Catch
Catch and Release Allowed
Disabled Accessible

15% deposit charged upfront by FishingBooker to guarantee your reservation. The remaining balance is to be paid directly to the captain on or prior to your trip date in one of the following payment methods: Cash, Visa, Mastercard, Checks.

About the Captain

Brad Simonds
Key West, Florida, United States
Member since May 2014
Capt. Brad has over 30 years of recreational and tournament sportfishing experience. Apart from running a charter business, he's also spent 9 years as a member of the Sanctuary Advisory Council to the Florida Keys National Marine Sanctuary.
Response time: 11 hours
Response rate: 79%

Key West Fishing Calendar

Customer Reviews

4.72 out of 5 stars from 6 reviews

5 stars
4 stars
3 stars
2 stars
1 star

Despite 25 knot winds, captain agreed to try to find protected waters. We are glad he did! He made our vacation. We caught numerous snapper varieties, a dozen blue tail that we released, and two large tuna. But the thrill of a lifetime was hooking a 150lb Goliath grouper. Took pictures of the aquarium worthy beast to prove it.
We have booked charters in Nassau Bahamas, and five times on Lake Michigan for fresh water salmon. Fishing the Southpaw was the largest number of catches by far.

Jennifer Szczesniak  • Fished December 30, 2016
  • Boat
  • Crew
  • Overall

My family and I had a wonderful time on the South paw with Captain Simmons and first mate matt who worked very hard to make sure we caught lots of Yellowtail snapper and grouper! We felt totally safe and at home on the spacious 43 footer and the crew were very patient with us beginners but especially with my 9 year old son who had a thousand questions for Captain Simmons! He was thrilled being able to ride up on top on with the captain who later filleted our fish and told us where to go to get it cooked can’t wait to do it again someday thanks again guys for a great experience! ...

Ron Curvelo  • Fished July 26, 2016
  • Boat
  • Crew
  • Overall

We were planning on going to Key West on vacation with family & friends & had always wanted to fish in the surrounding waters.
Fishing party was made up of my friend and myself with his 2 teenage sons.
Both adults had fished all over Scotland whilst 2 teenagers had never fished before.
Following on from all the positive reviews on trip advisor and Fishing booker we decided to book the Southpaw with Captain Brad for our trip.
All communication leading up to the trip was excellent and there were no issues at all.
Boat was clean and in good condition with plenty fishing rods / tackle on show.
We booked a ½ day trip and on the fishing front we did catch a variety of different fish with a few nice sized snappers on show.

The downside was captain Brad’s lack of enthusiasm and lack of fishing time for all members of the party.
There were 4 of us on board and we only had a maximum of 2 fishing at any one time whilst the other 2 could spend up to 20 mins sitting watching before we swapped over.
At one stage captain Brad was fishing himself whilst his mate assisted one of our party.
It appeared to be a chore to captain Brad that we were out fishing and various times when we were trying to make conversation he did not reply to us.
The teenage boys had not fished before and his teaching techniques / manner were more aggressive that we expected.
What should have been a fun day fishing was made less enjoyable by the less than enthusiastic captain.
Caught some nice fish and will certainly fish again when in the keys but not on Southpaw with Captain Brad.

Craig Mcfarlane  • Fished June 29, 2016
  • Boat
  • Crew
  • Overall