Business Details
Your Premier Key West Fishing Charter Experience
Southpaw Fishing Key West Key West has established itself as a premier destination for anglers seeking exceptional fishing charters in the Florida Keys. With over 40 years of experience navigating the waters of Key West, our award-winning captain, Brad Simonds, brings unparalleled expertise to every excursion. As an Orvis-endorsed guide and multiple winner of local and international fishing tournaments, Captain Brad combines deep local knowledge with a passion for delivering unforgettable fishing experiences. Our custom-built 43-foot charter vessel, SOUTHPAW, features the largest fishing cockpit in the fleet, state-of-the-art fish-finding electronics, and a working tuna tower for optimal sight fishing. We specialize in a variety of techniques including deep sea fishing, bottom fishing, kite fishing, and light tackle fishing, catering to both seasoned anglers and families introducing children to the sport.The boat's design prioritizes comfort and efficiency, with extra-large live well capacity and a meticulously maintained layout that maximizes fishing opportunities. Our dedicated crew ensures every client receives personalized attention while benefiting from our extensive tackle selection and premium live bait. Having served generations of anglers, including 30-year repeat clients, we maintain an unwavering commitment to quality that has made us a trusted name in Key West fishing. Our reputation for excellence is reflected in testimonials praising our professionalism, preparation, and ability to consistently deliver exceptional fishing results. Whether targeting sailfish, dolphin, or blackfin tuna, we provide the equipment, expertise, and local knowledge needed to transform fishing dreams into reality.
Services
Deep Sea Fishing
Bottom Fishing
Sailfishing
Dolphin Fishing
Take A Kid Fishing
Wreck Fishing
Kite Fishing
Light Tackle Fishing
Highlights and features
- 40 years of Florida Keys fishing expertise from award-winning captain
- Custom-built 43' charter boat with largest fishing cockpit in Key West
- Multiple international tournament-winning captain and crew
- Specialized techniques for sailfish, dolphin, and blackfin tuna
- Orvis-endorsed guide with professional-grade tackle selection
Associations and certifications
- Orvis
What people say
Experienced crew
Great service
Prime fishing grounds
Family-friendly environment
Exceptional catch rates
Services
Deep Sea Fishing
Our deep sea fishing charters target pelagic species in open waters using advanced trolling techniques. With our high-speed vessel and professional-grade tackle, we access prime fishing grounds quickly while providing expert guidance on targeting sailfish, marlin, and wahoo. Clients benefit from our captain's decades of tournament experience and intimate knowledge of migratory patterns.
Sailfishing
Specialized sailfishing excursions utilize live bait and kite fishing techniques to target these prized game fish. Our tuna tower and advanced electronics help locate concentrations, while our crew's tournament-winning expertise ensures optimal presentation. Recent reports show increased sailfish activity during winter months with multiple daily bites becoming routine.
Dolphin Fishing
We focus on productive dolphin fishing during summer months when these colorful fish congregate in abundance. Our custom live wells maintain premium baitfish, while our strategic approach to floating debris fields maximizes catch rates. Clients consistently report better-than-average dolphin catches compared to other Key West charters.
Light Tackle Fishing
Our light tackle specialists provide exciting challenges for anglers seeking skill-based fishing experiences. The SOUTHPAW's design accommodates specialized gear for species like snapper and grouper, with our crew offering real-time instruction on proper techniques. This approach appeals to clients wanting more engagement with the fishing process.
Take A Kid Fishing
Kid-friendly charters focus on educational experiences while maintaining fishing success. Our crew adapts techniques to children's abilities, provides safety instruction, and maintains appropriate tackle for younger anglers. Testimonials highlight our ability to make first-time fishing trips memorable while keeping experienced young anglers challenged.
People
Brad Simonds
Captain
Captain Brad Simonds brings 40 years of Florida Keys fishing expertise to Southpaw Fishing Key West Key West. A multiple international tournament winner and Orvis-endorsed guide, he specializes in sailfish, dolphin, and deep sea techniques while maintaining a reputation for exceptional client service.
Questions
What types of fishing charters do you offer?
We specialize in deep sea fishing, sailfishing, dolphin fishing, bottom fishing, and light tackle techniques. Our charters accommodate up to 6 anglers for half-day, three-quarter-day, or full-day excursions.
What makes your charter boat unique?
The 43' SOUTHPAW features the largest fishing cockpit in Key West, a working tuna tower, advanced fish-finding electronics, and premium live bait systems that set us apart from competitors.
Can beginners participate in your fishing charters?
Absolutely! Our crew provides expert guidance for all skill levels, including specialized 'Take A Kid Fishing' charters that balance education with successful fishing outcomes.
What fishing techniques do you specialize in?
We employ light tackle, live bait trolling, kite fishing, reef/wreck fishing, and blue water fly fishing techniques tailored to target species and seasonal patterns.
How do you handle equipment and tackle?
We provide professionally maintained tackle for all targeted species, including specialized gear for sailfish, dolphin, and light tackle applications. Clients may bring personal equipment if preferred.
What are your booking policies?
We recommend booking 4-6 weeks in advance for peak seasons. A deposit is required to secure reservations, with full payment due before departure. Specific policies are available on our website.
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