Southpaw Fishing Charters 

4.9/5 (247 reviews)
 
Federally permitted
 Oceans EdgeMarina 5950 Peninsular Ave, Key West, FL 33040, United States

Southpaw Fishing Charters 

 
Federally permitted
4.9/5 (247 reviews)
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Oceans EdgeMarina 5950 Peninsular Ave
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.

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Rating

4.9
247 reviews
5
230
4
10
3
4
2
0
1
0
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (324)

Knows his stuff
Great time despite weather
Attention to Detail
Attention to Detail
Attention to Detail
Awesome trip!!
+318

What anglers say

98%
Great experience
91%
Family friendly
97%
Friendly captain
100%
Good boat
96%
Recommended
95%
Caught fish

All reviews (247)

Filter
Showing 15 of 247 reviews
Quinton Bailey
Quinton Bailey
5.0
Verified
Unforgettable Experience
3/4 Day Trip on November 13, 20252 adults
Captain Brad and James were organized, tactical and hardworking - made for a successful and unforgettable trip. Choppy water but they made us feel very safe. Put us on 3 sailfish and caught plenty of eaters too. Could have brought us back to shore but fished to the last minute hunting down the 3rd sailfish. Sushi at the docks (incredible), filleted our fish, offered pictures, gave restaurant recommendations, gave us the leader of the first sailfish we ever caught - lots of attention to detail that made it excellent. James is incredibly hardworking and patient with all our questions…. Will be coming back!
Review media 0
Review media 1
Review media 1
Reported catch:
Sailfish
Dolphin (Mahi Mahi)
0
Brandon Taylor
Brandon Taylor
5.0
Verified
New
Great time despite weather
Half Day Trip (AM) on January 19, 20266 adults
Captain Brad and firstmate James were great. The wind was howling but we still went out. Had a blast. First time for most. Some pretty big waves but the action was still great, boat handled well. Would absolutely recommend and go with again. Boat was great
Review media 0
0
Michael Beres
Michael Beres
5.0
Verified
Attention to Detail
Full Day Trip on January 4, 20264 adults
Capt. Brad runs a top notch charter. His ship was extremely clean. He goes to great lengths to help you catch what you are looking for. In our case it was sailfish. We had a very successful trip. Also cannot say enough about first mate James. He was on top of line placment and didnt mind answering our children’s questions. I would highly recommend taking your children on Southpaw. We look forward to doing this again!
Review media 0
Review media 0
Review media 1
Reported catch:
Sailfish
Response from Captain
January 6, 2026
Thanks Michael for your review. we enjoyed having your family aboard.
0
Kimberly Jones
Kimberly Jones
5.0
Verified
Friendly crew, excellent boat, beautiful views!
Half Day Trip (AM) on June 17, 20252 adults
The captain and first mate were super friendly and very good at their jobs. The seas were a bit rocky for my liking so we came back a tad earlier than scheduled, but Captain Brad and James were very gracious about it. They put us right on the mahi and we reeled in about 8…5 of which were big enough to keep. The captain offered to clean them for us which we took him up on that. Watching him throw the fish carcasses into the water and see all the tarpon in a frenzy to eat them was entertaining in and of itself. Great experience all around!!!
Reported catch:
Dolphin (Mahi Mahi)
0
WILLIAM BATES
WILLIAM BATES
5.0
Verified
New
Knows his stuff
Dawn to Dusk on February 7, 20265 adults
Captain Brad and First Mate James know their fishing. They put us on tuna, snapper, mackerel, bonito, and more. Had an amazing day on the water when others got skunked. Best charter I’ve ever been on, and I’ll be back.
Review media 0
Reported catch:
King Mackerel (Kingfish)
Yellowtail Snapper
Blackfin Tuna
0

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
February 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
Half Day Trip (AM)
FREE Cancellation 7 days notice
4 Hour Trip
starts at 7:30 AM
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US $950
Entire boat: up to 6 people
Half Day Trip (PM)
FREE Cancellation 7 days notice
4 Hour Trip
starts at 1:00 PM
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US $950
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 7 days notice
6 Hour Trip
starts at 7:30 AM
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US $1,400
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 7 days notice
8 Hour Trip
starts at 7:30 AM
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US $1,600
Entire boat: up to 6 people
Dawn to Dusk
FREE Cancellation 7 days notice
11 Hour Trip
starts at 6:00 AM
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US $2,000
Entire boat: up to 6 people
There are 4 people looking at this charter.

Rating

4.9
247 reviews
5
230
4
10
3
4
2
0
1
0
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (324)

Knows his stuff
Great time despite weather
Attention to Detail
Attention to Detail
Attention to Detail
Awesome trip!!
+318

What anglers say

98%
Great experience
91%
Family friendly
97%
Friendly captain
100%
Good boat
96%
Recommended
95%
Caught fish

All reviews (247)

Filter
Showing 15 of 247 reviews
Quinton Bailey
Quinton Bailey
5.0
Verified
Unforgettable Experience
3/4 Day Trip on November 13, 20252 adults
Captain Brad and James were organized, tactical and hardworking - made for a successful and unforgettable trip. Choppy water but they made us feel very safe. Put us on 3 sailfish and caught plenty of eaters too. Could have brought us back to shore but fished to the last minute hunting down the 3rd sailfish. Sushi at the docks (incredible), filleted our fish, offered pictures, gave restaurant recommendations, gave us the leader of the first sailfish we ever caught - lots of attention to detail that made it excellent. James is incredibly hardworking and patient with all our questions…. Will be coming back!
Review media 0
Review media 1
Review media 1
Reported catch:
Sailfish
Dolphin (Mahi Mahi)
0
Brandon Taylor
Brandon Taylor
5.0
Verified
New
Great time despite weather
Half Day Trip (AM) on January 19, 20266 adults
Captain Brad and firstmate James were great. The wind was howling but we still went out. Had a blast. First time for most. Some pretty big waves but the action was still great, boat handled well. Would absolutely recommend and go with again. Boat was great
Review media 0
0
Michael Beres
Michael Beres
5.0
Verified
Attention to Detail
Full Day Trip on January 4, 20264 adults
Capt. Brad runs a top notch charter. His ship was extremely clean. He goes to great lengths to help you catch what you are looking for. In our case it was sailfish. We had a very successful trip. Also cannot say enough about first mate James. He was on top of line placment and didnt mind answering our children’s questions. I would highly recommend taking your children on Southpaw. We look forward to doing this again!
Review media 0
Review media 0
Review media 1
Reported catch:
Sailfish
Response from Captain
January 6, 2026
Thanks Michael for your review. we enjoyed having your family aboard.
0
Kimberly Jones
Kimberly Jones
5.0
Verified
Friendly crew, excellent boat, beautiful views!
Half Day Trip (AM) on June 17, 20252 adults
The captain and first mate were super friendly and very good at their jobs. The seas were a bit rocky for my liking so we came back a tad earlier than scheduled, but Captain Brad and James were very gracious about it. They put us right on the mahi and we reeled in about 8…5 of which were big enough to keep. The captain offered to clean them for us which we took him up on that. Watching him throw the fish carcasses into the water and see all the tarpon in a frenzy to eat them was entertaining in and of itself. Great experience all around!!!
Reported catch:
Dolphin (Mahi Mahi)
0
WILLIAM BATES
WILLIAM BATES
5.0
Verified
New
Knows his stuff
Dawn to Dusk on February 7, 20265 adults
Captain Brad and First Mate James know their fishing. They put us on tuna, snapper, mackerel, bonito, and more. Had an amazing day on the water when others got skunked. Best charter I’ve ever been on, and I’ll be back.
Review media 0
Reported catch:
King Mackerel (Kingfish)
Yellowtail Snapper
Blackfin Tuna
0

FAQs about Southpaw Fishing Charters

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Sportfishing boats
Capacity
6 persons
Boat length
43 ft
Year built
2002
Boat manufacturer
Torres
Boat type
Convertible

Engine model
Lugger
Powered by
1 x 700HP
Max cruising speed
19 knots
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