Southpaw Fishing Charters 

4.9/5 (277 reviews)
 
State licensed
 Oceans EdgeMarina 5950 Peninsular Ave, Key West, FL 33040, United States

Southpaw Fishing Charters 

State licensed
Key West, FL, United States
43 ft
6
4.9/5 (277 reviews)

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.

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.

Brad Simonds
Captain
Brad Simonds
42 years of experience
ID & credentials verified

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
July 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
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Almost there...
Half Day Trip
In high demand Last booked: 1 day ago
FREE Cancellation 7 days notice
4 hour trip multiple starting times (7:30 AM, 1:00 PM)
Amberjack
Dolphin (Mahi Mahi)
King Mackerel (Kingfish)
Sailfish
+5
US $1,000
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 7 days notice
6 hour trip starts at 7:30 AM
Dolphin (Mahi Mahi)
Sailfish
Tuna (Skipjack)
Grouper (Black)
+1
US $1,500
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 7 days notice
8 hour trip starts at 7:30 AM
Barracuda (Great)
Dolphin (Mahi Mahi)
Sailfish
Wahoo
US $1,800
Entire boat: up to 6 people
Dawn to Dusk
FREE Cancellation 7 days notice
11 hour trip starts at 6:00 AM
Amberjack
Dolphin (Mahi Mahi)
King Mackerel (Kingfish)
Sailfish
+6
US $2,500
Entire boat: up to 6 people
There are 7 people looking at this charter.

Customer reviews

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Rating

4.9
277 reviews
5.0
Boat & equipment
4.9
Captain & crew
4.9
Fishing Experience

Anglers' gallery (361)

What anglers say

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

All reviews (277)

Frequently mentioned
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Showing 15 of 277 reviews
Andrew Krug
Andrew Krug
us
Virginia, US
Member since 2025
5.0
Verified
All Around Amazing Experience
3/4 Day Trip on March 31, 20262 adults4 children

Everything from the Captain, first mate, the boat, the fishing equipment, and all things in-between was fantastic. James, the first mate, was informative and very kind to a number of our first timers. The Captain knew exactly where to go to catch our bait fish and sailfish. About ten minutes in fishing we hooked a sailfish. After about 30ish minutes we landed it. Captain Brad called the day before to confirm everything, provide info about the conditions, and made sure we knew how to find his boat at the marina. We honestly couldn't have asked for a better experience. Highly recommend.

Reported catch:
Sailfish
Sten Gustafson
Sten Gustafson
us
Texas, US
Member since 2026
5.0
Verified
New
Capt. Travis is awesome! Non-stop action
3/4 Day Trip on July 3, 20264 adults

Capt. Travis is one of the best fishing guides I've ever used (and I've used a lot). Great attitude and demeanor. He asked us what we were looking to catch, and he delivered tremendous fishing action for every kind of fish we were looking for (snapper, grouper, sharks) immediately the moment we pulled up to each spot. My son and nephews had a blast, and were wondering about whether we could come back soon. Highly recommend!

Deborah Cominski
Deborah Cominski
Repeat angler
us
North Carolina, US
Member since 2022
5 trips
5.0
Verified
New
Outstanding
3/4 Day Trip on July 6, 20262 adults

Everyone was complaining that they weren’t catching any fish. Captain Brad and first mate, James did not disappoint. James kept 7 plus lines going effortlessly and we caught seven different kinds of fish from red snapper to Mahi Mahi. Took it to a restaurant and ate it same day and shared it with the restaurant staff. Nothing like it. Melt in your mouth fish! Thanks Captain Brad and James!!

Reported catch:
Dolphin (Mahi Mahi)
Mutton Snapper
Quinton Bailey
Quinton Bailey
ca
Manitoba, Canada
Member since 2025
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!

Reported catch:
Sailfish
Dolphin (Mahi Mahi)
Lawrence Melanson
Lawrence Melanson
us
New Hampshire, US
Member since 2025
5.0
Verified
Great Boat. Great Crew.
Half Day Trip on June 6, 20264 adults

Capt. James and First Mate Jameson were awesome. Boat was clean and organized. Gear was top notch. The fish cooperated. Trolled for Mahi Mahi. At one point, three on at once. Jameson was ready with spinning gear if other fish followed the first one in. Jameson was great with our special needs son. They cleaned, filleted and bagged our catch. Highly recommend Southpaw Fishing.

Reported catch:
Dolphin (Mahi Mahi)

FAQs about Southpaw Fishing Charters

Southpaw Fishing Charters offers the following trips to customers:
  • US $1,000 per group - Half Day Trip (4 hours)
  • US $1,000 per group - Half Day Trip - 1:00 PM (4 hours)
  • US $1,500 per group - 3/4 Day Trip (6 hours)
  • US $1,800 per group - Full Day Trip (8 hours)
  • US $2,500 per group - Dawn to Dusk (11 hours)
When you book a trip with Southpaw Fishing Charters, you can expect the following amenities onboard:
  • Toilet Full sized bathroom with electric marine 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 (In the winter and spring our fishing is almost exclusively live bait fishing. There is no additional charge for live bait. Some days clients are expected to help catch bait.)
  • Lures
  • Catch cleaning & filleting (We clean and bag your fish free of charge)
  • Drinks (Soft drinks & water)
  • First mate (15% tip is expected)
  • Fishing license (The boat covers fishing licenses for all clients. There is no charge for your 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

Your captain

Brad Simonds
Brad Simonds
Brad Simonds

Key West, Florida, United States

10 Fishing Reports
ID & license verified
277 Customer reviews
Typical response within 2 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.

10 Fishing Reports
ID & license verified
277 Customer reviews
Typical response within 2 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.

The fish you can target

Amberjack
Amberjack
Great Barracuda
Great Barracuda
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Black Grouper
Black Grouper
King Mackerel (Kingfish)
King Mackerel (Kingfish)
Sailfish
Sailfish
Mangrove Snapper
Mangrove Snapper
Mutton Snapper
Mutton Snapper
Red Snapper
Red Snapper
Yellowtail Snapper
Yellowtail Snapper
Skipjack Tuna
Skipjack Tuna
Wahoo
Wahoo
Amberjack
Amberjack
Great Barracuda
Great Barracuda
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Black Grouper
Black Grouper
King Mackerel (Kingfish)
King Mackerel (Kingfish)

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

What kind of fishing will you do?

Offshore Fishing
Up to 20 miles
Reef Fishing
Wreck Fishing

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Spinning
Jigging
Fly Fishing
Drift Fishing
Kite Fishing
Deep Sea Fishing

Which amenities are available onboard

Toilet
Full sized bathroom with electric marine toilet
Fighting chair
GPS
Fishfinder
Flybridge
Live bait well
Outriggers
Ice box

What’s included in the trip price

Rods, reels & tackle
Penn, Shimano, Daiwa
Live bait
In the winter and spring our fishing is almost exclusively live bait fishing. There is no additional charge for live bait. Some days clients are expected to help catch bait.
Lures
Catch cleaning & filleting
We clean and bag your fish free of charge
Drinks
Soft drinks & water
First mate
15% tip is expected
Fishing license
The boat covers fishing licenses for all clients. There is no charge for your license.
Fly fishing equipment

How cancellations work

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.

More details

What the listing policies are

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

How you can pay

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

What’s biting in Key West right now

AmberjackAmberjack
Barracuda (Great)Barracuda (Great)
Dolphin (Mahi Mahi)Dolphin (Mahi Mahi)
Grouper (Black)Grouper (Black)
King Mackerel (Kingfish)King Mackerel (Kingfish)
SailfishSailfish
Snapper (Mangrove)Snapper (Mangrove)
Snapper (Mutton)Snapper (Mutton)
Snapper (Yellowtail)Snapper (Yellowtail)
Tuna (Skipjack)Tuna (Skipjack)
WahooWahoo

Compare similar fishing charters

Current
Southpaw Fishing Charters
Southpaw Fishing Charters
State licensed
4.9
(277)
43 ft
Group size 1 - 6
1 - 6
Fish 1
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+10
4 hour trip • 6 persons
US $1,000