Southpaw Fishing Charters

(24) In demand!
Oceans EdgeMarina 5950 Peninsu…
Key West FL, United States

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 hours trip, starts at 6:00 AM
    Seasonal trip available 1 Nov - 15 Aug
    US$ 1500
    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
      FREE Cancellation 7 days notice
    8 hours trip, starts at 7:30 AM
    Seasonal trip available 1 Nov - 15 Aug
    US$ 1200
    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
    In demand!
      FREE Cancellation 7 days notice
    6 hours trip, starts at 7:30 AM
    Seasonal trip available 1 Nov - 15 Aug
    US$ 1000
    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 Cancellation 7 days notice
    4 hours trip, starts at 7:30 AM
    Seasonal trip available 1 Nov - 15 Aug
    US$ 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 Cancellation 7 days notice
    4 hours trip, starts at 1:00 PM
    Seasonal trip available 1 Nov - 15 Aug
    US$ 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 3 people looking at this charter.

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

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 Cancellation
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

About the Captain

Brad Simonds
Key West, Florida, United States
Member since May 2014
24
2
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.
Response time: 3 hours
Response rate: 96%

Key West Fishing Calendar

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Customer Reviews

Rating Summary
Photos by reviewers (30)
4.82
out of 5 stars from 24 reviews
Boat
Crew
Experience
Awesome experience! Capt. Brad put us on the fish!
June fishing trip
Half day with Southpaw
+27
Angler Rating
21
1
2
0
0
Anglers Claimed
Good experience
95%
Friendly captain
100%
Recommend this charter
92%
Appropriate for children
100%
Satisfied with the boat
100%
Catch intended fish
95%
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5 of 24 reviews
Alan Ford
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 Ford recommends Southpaw Fishing Charters
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Steve Aubin
Erving, Massachusetts
 5.00
Experience:
Boat
Crew
Overall

3/4 day trip with Captain Brad Simonds

VERIFIED   April 3, 2018
4/3/18 - Treated myself to a birthday gift with a 3/4 day trip with Brad - outstanding day. I am a New Englander used to striper...
Steve Aubin recommends Southpaw Fishing Charters
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David Clark
Key West, Florida
 5.00
Experience:
Boat
Crew
Overall

Three days with captain Brad and Matt

VERIFIED   March 8, 2018
A group of us fished 3 days on the Southpaw with captain Brad Simonds and his mate Matt. We are all experienced fisherman but...
David Clark recommends Southpaw Fishing Charters
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Brad Lord
Lady Lake, FL
 5.00
Experience:
Boat
Crew
Overall

3/4 day trip

VERIFIED   August 9, 2018
My wife and son joined me for a great day of key west fishing. Was a bit late in the season, but capt Brad worked hard to get...
Brad Lord recommends Southpaw Fishing Charters
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Ricky Knappenberger
DeRidder, Louisiana
 5.00
Experience:
Boat
Crew
Overall

Had a great time catching fish!!

VERIFIED   May 25, 2018
Captain Brad & his deck hand Matt where great trying to keep us on fish. The weather was bad rough seas and rain. Over...
Ricky Knappenberger recommends Southpaw Fishing Charters
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  Brad Simonds Captain replied