Capt. Brad Simonds owns and operates Southpaw Fishing Charters. He’ll take you on exciting fishing trips aboard a 43’ custom-built Torres Sportfisher, constructed in 2002 by Claude Torres, a distinguished boat builder. The boat is powered by a 700 HP Lugger diesel engine, and comes outfitted with a comprehensive package of navigational and marine electronics. These include 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. Those include Billfish, Tuna, Mahi Mahi, Kingfish, Snapper, Grouper and many others. Custom fishing trips 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.



Select date to see available trips and rates:

  • Private trip
    Dawn to Dusk
    FREE Cancellation 7 days notice
    11 Hour Trip, starts at 6:00 AM
    $1,800
    Fishing the reefs, wrecks, and blue waters far to the west of Key West. This trip is perfect to get some serious fishing done in waters under less pressure. The captain will supply you with all the required equipment.
  • Private trip
    Full Day Trip
    FREE Cancellation 7 days notice
    8 Hour Trip, starts at 7:30 AM
    $1,400
    A full day trip gives you the time to run to more distant areas and experience even better fishing than on shorter trips. Expect to target Marlin, Sailfish, Mahi Mahi, Barracuda, and other prestigious species.
  • Private trip
    3/4 Day Trip
    FREE Cancellation 7 days notice
    6 Hour Trip, starts at 7:30 AM
    $1,200
    A 3/4 day trip allows you the chance to experience multiple types of fishing on the same trip. Spend half of your time trolling the blue water for Sailfish, Tuna, and Mahi Mahi then anchor down on a reef or wreck for Snapper and Grouper.
  • Private trip
    Half Day Trip (AM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 7:30 AM
    $800
    Short runs to the fishing grounds ensure a maximum amount of fishing time. You will target seasonal abundances of many different game fish, from Sailfish to Snapper including Tuna, Wahoo, Mackerel, Mahi Mahi, and Grouper.
  • Private trip
    Half Day Trip (PM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 1:00 PM
    $800
    Sleep in and then go fishing, what can beat starting your day off like that? You'll go after a wide range of exciting species like Groupers, Snappers, Amberjack, Barracuda, Mahi Mahi, maybe even a Sailfish or Marlin will wander in your range!
There are 25 people looking at this charter.

About the Captain

Brad Simonds
Key West, Florida, United States
6 Fishing Reports
ID & License verified
117 Customer Reviews
Response time 3 hours
Member since May 2014
Capt. Brad has 40 years of charter fishing 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 representing the charter boat industry. He welcomes anglers of all skill levels on board – he can help you from teaching basics to a first-timer to providing assistance to a seasoned sea wolf.

About this listing

Targeted Species

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

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

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

Boat Specs

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

Length
43 ft
Capacity
6 persons

Types of Fishing

Offshore Fishing
Reef Fishing
Wreck Fishing

Fishing Techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Spinning
Jigging
Fly Fishing
Drift Fishing
Kite Fishing
Deep Sea Fishing

Amenities

Toilet
Fighting Chair
GPS
Fishfinder
Flybridge
Live Bait Well
Outriggers
Ice Box
Toilet
Fighting Chair
GPS
Fishfinder
Flybridge
Live Bait Well

Trip Includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Drinks
First Mate
Fishing License
Fly Fishing Equipment

Cancellation Policy

Free cancellation up to 7 days prior to trip

Customers can cancel or modify their booking up to 7 days before the trip date free of charge. If the trip is canceled or modified later, or in the event of a no-show, 100% of the deposit will be charged.

Listing Policies

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

Payment

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:
Cash
Visa
Mastercard
Checks

Key West Fishing Calendar

Loading Fish Calendar!
Please Wait...

Customer Reviews

Rating Summary
Photos & videos by reviewers (174)
4.88
Excellent Excellent Excellent Excellent Excellent
out of 5 stars from 117 reviews
Boat
Excellent Excellent Excellent Excellent Excellent
Crew
Excellent Excellent Excellent Excellent Excellent
Experience
Excellent Excellent Excellent Excellent Excellent
Southpaw for the Win!
Southpaw for the Win!
Southpaw for the Win!
+171
Angler Rating
107
5
4
0
0
Anglers Claimed
Good experience
97%
Friendly captain
97%
Recommend this charter
96%
Appropriate for children
92%
Satisfied with the boat
100%
Catch intended fish
93%
Sort By:
Featured  
Showing:
5 of 117 reviews
Rodney C.
Key West, Florida
Excellent Excellent Excellent Excellent Excellent  5.00
Experience:
Excellent Excellent Excellent Excellent Excellent Boat
Excellent Excellent Excellent Excellent Excellent Crew
Excellent Excellent Excellent Excellent Excellent Overall

3/4 day trip

VERIFIED   NEW  Full Day Trip on June 25, 2021
We had scheduled a full day trip with Captain Brad, but the weather cut us down to 3/4 day. We had a great time catching dolphinfish!...
Rodney C. recommends Southpaw Fishing Charters
Mark as helpful
You found this helpful
Rodney C. recommends Southpaw Fishing Charters
Mark as helpful
You found this helpful

Jai I.
Riverview, Florida
Excellent Excellent Excellent Excellent Excellent  5.00
Experience:
Excellent Excellent Excellent Excellent Excellent Boat
Excellent Excellent Excellent Excellent Excellent Crew
Excellent Excellent Excellent Excellent Excellent Overall

3/4 day

VERIFIED   NEW  3/4 Day Trip on June 29, 2021
We had an outstanding day of fishing with Southpaw Charters. Capt Brad put us on the fish and Mitch was an excellent mate (Parker...
Jai I. recommends Southpaw Fishing Charters
Mark as helpful
You found this helpful
Jai I. recommends Southpaw Fishing Charters
Mark as helpful
You found this helpful

Ryan F.
Hiawatha, IA
Excellent Excellent Excellent Excellent Excellent  5.00
Experience:
Excellent Excellent Excellent Excellent Excellent Boat
Excellent Excellent Excellent Excellent Excellent Crew
Excellent Excellent Excellent Excellent Excellent Overall

Fantastic Experience with this crew!

VERIFIED   3/4 Day Trip on May 17, 2021
Captain and First mate Mick were truly incredible on this experience. They were prepared early when we arrived so we could...
Ryan F. recommends Southpaw Fishing Charters
Mark as helpful
You found this helpful
  Brad Simonds Captain replied

Matt S.
Excellent Excellent Excellent Excellent Excellent  5.00
Experience:
Excellent Excellent Excellent Excellent Excellent Boat
Excellent Excellent Excellent Excellent Excellent Crew
Excellent Excellent Excellent Excellent Excellent Overall

Half Day with tons of action

VERIFIED   Half Day Trip (PM) on March 31, 2021
Have taken many charters and this was one of the very best.  The Southpaw is probably the best designed fishing boat I have...
Matt S. recommends Southpaw Fishing Charters
Mark as helpful
You found this helpful
  Brad Simonds Captain replied

Denis W.
Bradenton, FL
Excellent Excellent Excellent Excellent Excellent  5.00
Experience:
Excellent Excellent Excellent Excellent Excellent Boat
Excellent Excellent Excellent Excellent Excellent Crew
Excellent Excellent Excellent Excellent Excellent Overall

2 days with Captain Brad and first mate Mick

VERIFIED   Full Day Trip on February 16, 2021
Our first day was a bit bumpy because of the wind. But Capt Brad took us out to the reef and put us on some nice Snapper, Mackerel...
Denis W. recommends Southpaw Fishing Charters
Mark as helpful
You found this helpful
  Brad Simonds Captain replied

FAQs about Southpaw Fishing Charters

Southpaw Fishing Charters offers the following trips to customers:
  • $800 per group - Half Day Trip (AM) (4 hours)
  • $800 per group - Half Day Trip (PM) (4 hours)
  • $1,200 per group - 3/4 Day Trip (6 hours)
  • $1,400 per group - Full Day Trip (8 hours)
  • $1,800 per group - Dawn to Dusk (11 hours)

When you book a trip with Southpaw Fishing Charters, you can expect the following amenities onboard:
  • Toilet
  • Fighting Chair
  • GPS
  • Fishfinder
  • Flybridge
  • Live Bait Well
  • Outriggers
  • Ice Box

Trips booked with Southpaw Fishing Charters include:
  • Rods, reels & tackle (Penn, Shimano, Daiwa)
  • Live Bait
  • Lures
  • Catch cleaning & filleting
  • Drinks (Soft drinks & water)
  • First Mate (15% tip is expected)
  • Fishing License
  • Fly Fishing Equipment

Southpaw Fishing Charters offers the following types of fishing:
  • Offshore Fishing (Up to 20 miles)
  • Reef Fishing
  • Wreck Fishing

Southpaw Fishing Charters offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Trolling
  • Spinning
  • Jigging
  • Fly Fishing
  • Drift Fishing
  • Kite Fishing
  • Deep Sea Fishing

Top targeted fish species with Southpaw Fishing Charters include:
  • Amberjack
  • Barracuda (Great)
  • Dolphin (Mahi Mahi)
  • Grouper (Black)
  • King Mackerel (Kingfish)
  • Sailfish
  • Snapper (Mangrove)
  • Snapper (Mutton)
  • Snapper (Red)
  • Snapper (Yellowtail)
  • Tuna (Skipjack)
  • Wahoo