Southpaw Fishing Charters

4.9/5 (262 reviews)

Federally permitted

Oceans EdgeMarina 5950 Peninsular Ave, Key West, FL 33040, United States–

Meet the Captain

Southpaw Fishing Charters

Federally permitted

4.9/5 (262 reviews)

Meet the Captain

Oceans EdgeMarina 5950 Peninsular Ave

Key West, FL, United States

Trips & prices Targeted species Boat info What's biting What's included Contact captain

Trips & prices What's included Targeted species Boat info Reviews Contact captain

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.

Popular features

Fishing license

Live bait

You keep catch

Catch cleaning & filleting

Drinks

Popular features

Fishing license

Live bait

You keep catch

Catch cleaning & filleting

Drinks

Rating

4.9

262 reviews

243

5.0

Boat & equipment

4.9

Captain & crew

4.9

Fishing Experience

Anglers' gallery (341)

Two anglers standing on the deck of a sportfishing boat, preparing for a day of deep-sea fishing in open waters.

Two anglers proudly displaying a large Mahi Mahi while fishing in open waters.

A smiling angler gives a thumbs up next to a display of freshly caught fish, including several species, at a dockside cleaning station.

Two anglers proudly displaying their catch of large tuna while fishing offshore, showcasing a beautiful day on the water.

A colorful platter of sushi ingredients, featuring rice, fish, and various toppings, served in a casual dining setting.

Two anglers proudly displaying a large Snapper while fishing offshore, showcasing a successful day on the water.

+335

What anglers say

97%

Great experience

91%

Family friendly

97%

Friendly captain

100%

Good boat

96%

Recommended

95%

Caught fish

All reviews (262)

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Featured

Showing 1 – 5 of 262 reviews

Andrew Krug

Virginia, US

•

Member since 2025

5.0

Verified

All Around Amazing Experience

3/4 Day Trip on March 31, 2026 • 2 adults • 4 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:

Theodore Kocak

Repeat angler

Tennessee, US

•

Member since 2023

•

7 trips

5.0

Verified

New

Southpaw Captain Brad Simonds

Half Day Trip on May 7, 2026 • 2 adults

I have fished with Captain Brad when in Key West over the past 20yrs, In my opinion he is best Captain I have ever fished with and we always catch a great variety of fish. We fished May 6th and 7th and have 40lbs of fillets to bring home. Caught a sailfish this trip, snappers, mahi mahi are just some this trip.

An angler filleting a freshly caught fish on a cleaning station at the dock, with boats visible in the background.

Four Mahi Mahi laid out on a cleaning table at the dock, showcasing a successful fishing trip.

Reported catch:

Quinton Bailey

Manitoba, Canada

•

Member since 2025

5.0

Verified

Unforgettable Experience

3/4 Day Trip on November 13, 2025 • 2 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!

A fisherman holding a plate of freshly prepared fish fillets with dipping sauce at the dock, showcasing the catch of the day.

An angler is reeling in a Sailfish while fishing in deep blue waters, showcasing the excitement of sport fishing.

A variety of fish including Mahi Mahi and Spanish Mackerel displayed on a cleaning table at the dock, showcasing a successful fishing trip.

Reported catch:

Michael Beres

Georgia, US

•

Member since 2025

5.0

Verified

Attention to Detail

Full Day Trip on January 4, 2026 • 4 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!

An angler actively reeling in a large fish while fishing in deep blue waters, showcasing the excitement of sport fishing.

The image captures the mast of a fishing boat adorned with white flags against a clear blue sky, surrounded by palm trees, showcasing a tropical fishing environment.

A family proudly displays a large Sailfish on a fishing charter, showcasing a successful day on the water.

Reported catch:

Response from Captain

January 6, 2026

Thanks Michael for your review. we enjoyed having your family aboard.

Michael Davis

Colorado, US

•

Member since 2026

5.0

Verified

New

A lot of fun.

3/4 Day Trip on April 26, 2026 • 2 adults

We came down to fish for two days. Purposely booked two different charters. South paw was definitely the better of the two. Seems like the captain definitely tried harder and definitely impressed with his efforts. Overall a very good day.

Two anglers enjoying a sunset on a fishing boat, with fishing rods ready for action.

Three anglers relaxing inside the cabin of a spacious fishing boat, enjoying the ocean view.

A variety of freshly caught fish fillets displayed on a cleaning table at the dock, showcasing the day's catch.

Reported catch:

Trip availability and prices

Trip Date:

Days:

Group Size:

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May 2026

Su	Mo	Tu	We	Th	Fr	Sa

Number of days

Group Size

2 adults • 0 children

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Half Day Trip

FREE Cancellation 7 days notice

4 hour trip multiple starting times (7:30 AM, 1:00 PM)

US $1,000