Southpaw Fishing Charters

(15) Selling out fast!
Oceans EdgeMarina 5950 Peninsu…
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.

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

Select date to see available trips and rates:

Trip Date:
  • Dawn to Dusk
    11 hour trip, starts at 6:00 AM
    US$ 1400 private charter
  • Full Day Trip
    8 hour trip, starts at 7:30 AM
    US$ 1200 private charter
  • 3/4 Day Trip
    6 hour trip, starts at 7:30 AM
    US$ 900 private charter
  • Half Day Trip AM
    4 hour trip, starts at 7:30 AM
    US$ 700 private charter
  • Half Day Trip PM
    4 hour trip, starts at 1:00 PM
    US$ 700 private charter
There are 4 people looking at this charter.

About this listing

Targeted Species

  Barracuda (Great)
  Dolphin (Mahi Mahi)
  Grouper (Black)

  King Mackerel (Kingfish)
  Snapper (Mangrove)
  Snapper (Mutton)

  Snapper (Red)
  Snapper (Yellowtail)
  Tuna (Skipjack)

Boat Specs

Torres (Convertible) originally built in 2002. Powered by a 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


Fighting Chair
Life Jackets
Live Bait Well
Ice Box
Fighting Chair
Life Jackets

Trip Includes

Rods, reels & tackle
Live Bait
Catch cleaning & filleting
First Mate
Fishing License Included


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.
Child Friendly
You Keep Catch
Catch and Release Allowed
Disabled Accessible


Book with 15% deposit
When the captain confirms your trip, FishingBooker charges your credit card a 15% deposit to guarantee your reservation.
Pay remaining balance to captain
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

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: 4 hours
Response rate: 94%

Key West Fishing Calendar

Customer Reviews

4.71 out of 5 stars from 15 reviews

5 stars
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1 star

A group of us fished 3 days on the Southpaw with captain Brad Simonds and his mate Matt. We are all experienced fisherman but this was only our second year fishing Key West so we were still looking for a solid captain. Without question this was the most professional boat and crew I have ever used. They were spot on with a super clean boat every day and during the trip. Their equipment was varied and all in excellent working order because it is well maintained. Brad and Matt worked hard constantly keeping us on fish and making sure we were always tied up. They used several new fishing techniques and taught us some new stuff. They were patient and helpful and very friendly. Most importantly they sent us home with tasty fish and helped us land a sailfish double in the last day - awesome! Brad cleaned all our fish and even gave us some wasabi and soy to eat sushi on the dock. We will be repeat customers for sure - thanks a lot guys! Come up and see us in Gainesville when you can and we’ll treat you good!

Fished March 8, 2018
Brad Simonds (The Captain)
Replied to this review on March 11, 2018

Thanks Dave for your kind review
We look forward to your next trip

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Beautiful boat and hard-working talented captain and mate.  Despite poor fishing conditions we caught fish!  I would highly recommend them!

Fished February 12, 2018
Brad Simonds (The Captain)
Replied to this review on February 14, 2018

Thanks for your kind review. We are always a little disappointed when the fish don’t cooperate to our satisfaction. We look forward to better fishing on your next trip.
Capt. Brad

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Fished January 17, 2018
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