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.
  • Private trip
    Half Day Trip (PM)
    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!
  • Private trip
    3/4 Day Trip
    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.
  • 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.
  • Private trip
    Dawn to Dusk
    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.
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About the Captain

Brad Simonds
Key West, Florida, United States
6 Fishing Reports
ID & License verified
152 Customer reviews
Response time 5 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

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
No min. age, life jackets supplied
You Keep Catch
Catch and Release Allowed
Disabled Accessible

Payment

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

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Customer reviews

Rating Summary
Excellent
4.9 / 5
out of 5 stars from 152 reviews
Boat
Excellent
5.0 / 5
Crew
Excellent
4.8 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (210)
3\/4 day trip
3\/4 trip
3\/4 trip
+207
Angler Rating
135
10
4
0
0
Anglers Claimed
Good experience
96%
Friendly captain
95%
Recommend this charter
95%
Appropriate for children
91%
Satisfied with the boat
100%
Catch intended fish
90%
Sort By:
Featured  
Showing:
5 of 152 reviews
David D.
Bentonville, AR
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Full Day Trip with Captain Brad and 1st Mate Mick

VERIFIED   Full Day Trip on May 29, 2022
We had an excellent experience.  Captain Brad worked hard on finding the Mahi and never skimped on driving all over the place...
David D. recommends Southpaw Fishing Charters
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You found this review helpful
  Brad Simonds Captain replied

Mark F.
Key West, FL
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Day Trip on the Southpaw

VERIFIED   Dawn to Dusk on April 17, 2022
Wife and I had a Great trip with Captain Brad and First Mate Mick.  First half of day spent kite fishing, targeting Sailfish,...
Mark F. recommends Southpaw Fishing Charters
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You found this review helpful
  Brad Simonds Captain replied

Jacob R.
Savannah, GA
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

3/4 trip

VERIFIED   3/4 Day Trip on June 24, 2022
Captain warned us of the slow bite at this time and still got us on. 2nd time with Capt. Brad this guy knows what’s he’s...
Jacob R. recommends Southpaw Fishing Charters
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  Brad Simonds Captain replied

Steve V.
Westminster, CO
Very good
4.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Good
3.0 / 5
Crew
Very good
4.0 / 5
Overall

Full day. Captain Brad. Deck mate Mick

VERIFIED   Full Day Trip on April 28, 2022
Captain Brad and Mick are knowledgeable and very competent. The fish were biting on this day and we limited on Mahi and also...
Steve V. recommends Southpaw Fishing Charters
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Steve V. recommends Southpaw Fishing Charters
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Malcolm B.
Secaucus, New Jersey
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Amazing half day with Brad

VERIFIED   Half Day Trip (PM) on June 6, 2022
My son and I are complete novices, yet with the skillful skippering from Brad and expert guidance from Basha we managed to...
Malcolm B. recommends Southpaw Fishing Charters
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Malcolm B. recommends Southpaw Fishing Charters
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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