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
    Half Day Trip (AM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 7:30 AM
    $850
    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.
    Targeted fish
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    King Mackerel (Kingfish)
    King Mackerel (Kingfish)
    Tuna (Skipjack)
    Skipjack Tuna
    Wahoo
    Wahoo
    Grouper (Black)
    Black Grouper
  • Private trip
    Half Day Trip (PM)
    Just booked! Last booked: 5 hours ago
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 1:00 PM
    $850
    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!
    Targeted fish
    Amberjack
    Amberjack
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Sailfish
    Sailfish
    Tuna (Skipjack)
    Skipjack Tuna
    Snapper (Mangrove)
    Mangrove Snapper
    Grouper (Black)
    Black Grouper
    Snapper (Mutton)
    Mutton Snapper
  • Private trip
    3/4 Day Trip
    In demand! Last booked: 5 days ago
    FREE Cancellation 7 days notice
    6 Hour Trip, starts at 7:30 AM
    $1,300
    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.
    Targeted fish
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Sailfish
    Sailfish
    Tuna (Skipjack)
    Skipjack Tuna
    Grouper (Black)
    Black Grouper
    Snapper (Mutton)
    Mutton Snapper
  • Private trip
    Full Day Trip
    FREE Cancellation 7 days notice
    8 Hour Trip, starts at 7:30 AM
    $1,500
    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.
    Targeted fish
    Barracuda (Great)
    Great Barracuda
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Sailfish
    Sailfish
    Wahoo
    Wahoo
  • Private trip
    Dawn to Dusk
    In demand! Last booked: 1 day ago
    FREE Cancellation 7 days notice
    11 Hour Trip, starts at 6:00 AM
    $2,000
    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.
There is 1 person looking at this charter.

FAQs about Southpaw Fishing Charters

Southpaw Fishing Charters offers the following trips to customers:
  • $850 per group - Half Day Trip (AM) (4 hours)
  • $850 per group - Half Day Trip (PM) (4 hours)
  • $1,300 per group - 3/4 Day Trip (6 hours)
  • $1,500 per group - Full Day Trip (8 hours)
  • $2,000 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

Meet the Captain

Brad Simonds
Key West, Florida, United States
7 Fishing Reports
ID & license verified
167 Customer reviews
Response time 4 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) Great Barracuda
Dolphin (Mahi Mahi) Dolphin (Mahi Mahi)
Grouper (Black) Black Grouper

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
Up to 20 miles
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

Trip includes

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

Cancellation policy

Free cancellation up to 7 days prior to trip

You can cancel or modify your booking up to 7 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

Listing policies

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
No min. age, life jackets supplied
You Keep Catch
Catch and Release Allowed
Disabled Accessible

Payment

Pay online in full

Pay online in full through FishingBooker and save on credit card fees at the dock.

No additional fees.
Book with 15% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 15% deposit to guarantee your reservation.

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...

Recent fishing reports

IGFA 2023 Tommy Gifford award recipient
IGFA 2023 Tommy Gifford award recipient
October 26, 2023
On Oct 26, 2023 Capt Brad was honored with the Tommy Gifford award by the IGFA, International Gamefish Association. This Award based on lifetime achievement is the most prestigious honor a saltwater Capt can earn.
Continue reading

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 167 reviews
Boat
Excellent
5.0 / 5
Crew
Excellent
4.8 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (234)
Highly Recommend
Highly Recommend
Highly Recommend
+231
Angler rating
150
10
4
0
0
Anglers claimed
Good experience
97%
Friendly captain
96%
Recommend this charter
95%
Appropriate for children
91%
Satisfied with the boat
100%
Caught fish
91%
Sort by:
Featured  
Showing:
5 of 167 reviews
Tyler B.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Brad

VERIFIED   Full Day Trip on June 17, 2023
Tyler B. recommends Southpaw Fishing Charters
Mark review as helpful
You found this review helpful
Tyler B. recommends Southpaw Fishing Charters
Mark review as helpful
You found this review helpful

Elsa M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Highly Recommend

VERIFIED   NEW  Full Day Trip on December 2, 2023
We feel very appreciative for Captain Brad and mate. They were genuinely concerned that we have a good experience on our first...
Elsa M. recommends Southpaw Fishing Charters
Mark review as helpful
You found this review helpful
Elsa M. recommends Southpaw Fishing Charters
Mark review as helpful
You found this review helpful

John M.
Brighton, MI
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half day trip with Capt. Brad

VERIFIED   Half Day Trip (AM) on December 31, 2022
The boat was immaculate! Ryan, the first mate, worked tirelessly getting rods set and helping us reel in our catches. Captain...
John M. recommends Southpaw Fishing Charters
Mark review as helpful
You found this review helpful
  Brad Simonds Captain replied

Charles M.
Pompano Beach, FL
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great morning with Capt.Brad

VERIFIED   Half Day Trip (AM) on April 15, 2023
We had a great morning out on the Southpaw. Capt. Brad and mate Sean worked hard to put us on the fish and we put 12 in the...
Charles M. recommends Southpaw Fishing Charters
Mark review as helpful
You found this review helpful
  Brad Simonds Captain replied

Clint F.
Key West, Florida
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half day trip

VERIFIED   Half Day Trip (PM) on March 22, 2023
Great day with Captain Brad and Sean aboard the southpaw! Everyone caught fish and Capt Brad truly catered to our needs with...
Clint F. recommends Southpaw Fishing Charters
Mark review as helpful
You found this review helpful
Clint F. recommends Southpaw Fishing Charters
Mark review as helpful
You found this review helpful