Southpaw Fishing Charters

(48) In demand!

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 Cancelation 7 days notice
    11 hours trip, starts at 6:00 AM
    Seasonal trip available 1 Nov - 15 Aug
    $1,500
    up to 6 persons
    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
    In demand!
      FREE Cancelation 7 days notice
    8 hours trip, starts at 7:30 AM
    Seasonal trip available 1 Nov - 15 Aug
    $1,200
    up to 6 persons
    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 Cancelation 7 days notice
    6 hours trip, starts at 7:30 AM
    Seasonal trip available 1 Nov - 15 Aug
    $1,000
    up to 6 persons
    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 Cancelation 7 days notice
    4 hours trip, starts at 7:30 AM
    Seasonal trip available 1 Nov - 15 Aug
    $800
    up to 6 persons
    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 Cancelation 7 days notice
    4 hours trip, starts at 1:00 PM
    Seasonal trip available 1 Nov - 15 Aug
    $800
    up to 6 persons
    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 21 people looking at this charter.

About the Captain

Brad Simonds
Key West, Florida, United States
Angler's Choice
2 reports
ID & License verified
48 Customer Reviews
Response time 2 hours
Member since May 2014
Capt. Brad has over 38 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
Barracuda (Great)
Dolphin (Mahi Mahi)
Grouper (Black)

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

Snapper (Red)
Snapper (Yellowtail)
Tuna (Skipjack)
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
Life Jackets
Fishfinder
Flybridge
Live Bait Well
Outriggers
Ice Box
Toilet
Fighting Chair
GPS
Life Jackets
Fishfinder
Flybridge

Trip Includes

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

Policies

FREE Cancelation
You can cancel or reschedule your booking up to 7 days before the trip. If the captain cannot run the trip due to unsafe weather conditions, your booking can be moved to another date or canceled free of charge.
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

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Customer Reviews

Rating Summary
Photos by reviewers (57)
4.83
out of 5 stars from 48 reviews
Boat
Crew
Experience
Awesome trip with Captain Brad!!
Awesome trip with Captain Brad!!
Awesome trip with Captain Brad!!
+54
Angler Rating
43
2
3
0
0
Anglers Claimed
Good experience
95%
Friendly captain
95%
Recommend this charter
92%
Appropriate for children
98%
Satisfied with the boat
100%
Catch intended fish
93%
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Showing:
5 of 48 reviews
Eric C.
Miami, Florida
 5.00
Experience:
Boat
Crew
Overall

Awesome trip with Captain Brad!!

VERIFIED   NEW  June 19, 2019
Amazing trip with Southpaw Charters. Captain Brad was honest upfront with conditions and his knowledge of the area is top notch....
Eric C. recommends Southpaw Fishing Charters
Mark as helpful
You found this helpful
  Brad Simonds Captain replied

Bart C. T.
Miami, Florida
 5.00
Experience:
Boat
Crew
Overall

Full day with the best

VERIFIED   May 16, 2019
Had a great trip with Capt Brad and his mate Mick. They both worked tirelessly for the whole day until our box was full of...
Bart C. T. recommends Southpaw Fishing Charters
Mark as helpful
You found this helpful
  Brad Simonds Captain replied

Keith P.
Key West, FL
 5.00
Experience:
Boat
Crew
Overall

Great day with Captain Brad on Southpaw Charter

VERIFIED   November 16, 2018
We had a November cold front move through just ahead of our scheduled 3/4 day trip and it was predicted to be blowing pretty...
Keith P. recommends Southpaw Fishing Charters
Mark as helpful
1 person finds this review helpful
You and 1 other person found this helpful
  Brad Simonds Captain replied

Brian H.
Newark, NJ
 5.00
Experience:
Boat
Crew
Overall

6 hr mahi mahi trip

VERIFIED   NEW  May 29, 2019
The boat is spotless with a fully functional head. Captain and mate are true professionals. Tough day on rough seas resulted...
Brian H. recommends Southpaw Fishing Charters
Mark as helpful
You found this helpful
  Brad Simonds Captain replied

Alan F.
Sarasota, FL
 5.00
Experience:
Boat
Crew
Overall

Great day

VERIFIED   July 6, 2018
What a GREAT day fishing!!!  Such a good time and i cant say enough about the Capt. and his mate.  We were put on...
Alan F. recommends Southpaw Fishing Charters
Mark as helpful
1 person finds this review helpful
You and 1 other person found this helpful
  Brad Simonds Captain replied

Weather Protection
Weather Protection
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