Charter fishing in Key West with award winning Capt. Brad Simonds aboard his 43′ custom built charter fishing vessel, SOUTHPAW. Key West fishing charters for up to 6 anglers. Highly skilled fishing crew is kid friendly and courteous. Capt. Brad Simonds has over 30 years of experience in Florida Keys waters. A multiple time winner of both local and international fishing tournaments as well as an Orvis endorsed guide.With our world travel planner, Key West attractions like Southpaw Fishing can be center stage of your vacation plans, and you can find out about other attractions like it, unlike it, near it, and miles away.
Deep Sea Fishing, Bottom Fishing, Wreck Fishing, Kite Fishing, Live Bait Fishing, Light Tackle Fishing
Our vessel is clean and well maintained with the biggest fishing cockpit in the fleet. Don’t settle for less, fish the best- SOUTHPAW.
Southpaw Fishing reviews
We had a BLAST on Southpaw with Captain Brad and Mick the mate. The description couldn’t be any more accurate. We had three adults and 4 kids (7-11). This trip was superb!!! The kids all got to... more »
Thanks Captain Brad and Mick! You guys really know your stuff. We had a fun day on the water. After catching plenty of yellow tail for the cooler, we added a late day sailfish! Dinner and a show! more »
Plan your trip to Key West
Get a personalized planA complete day by day itinerary
based on your preferences
Customize itRefine your plan. We'll find the
best routes and schedules
Manage itEverything in one place.
Everyone on the same page.
See all ›
Hidden gems in Key West
Side trips from Key West
See all ›
See all ›
Nearby attractions in Key West
Plans in Key West by other users
23 days in Florida & Louisiana BY A USER FROM ISRAEL September, teens, kids, popular sights Preferences: September, teens, kids Attraction style: Popular sights Pace: Medium 8 days in Florida BY A USER FROM UNITED STATES December, popular sights Preferences: December Attraction style: Popular sights Pace: Medium 4 days in Florida BY A USER FROM UNITED STATES November, popular sights Preferences: November Attraction style: Popular sights Pace: Medium 3 days in Florida Keys BY A USER FROM UNITED STATES November, teens, kids, popular sights Preferences: November, teens, kids Attraction style: Popular sights Pace: Medium 5 days in United States BY A USER FROM UNITED STATES April, romantic, popular & hidden gems Preferences: April, romantic Attraction style: Popular & hidden gems Pace: Medium 60 days in United States BY A USER FROM AUSTRALIA November, popular sights Preferences: November Attraction style: Popular sights Pace: Medium