Your Captain
Emmanuel Silva
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Experience the thrill of offshore fishing in Key West, Florida, with High Line Charters! Join Captain Phil Leonard, a seasoned local angler with years of experience, for an unforgettable day on the water chasing some of the most exciting game fish the Keys have to offer.
Step aboard the 39’ Key West sportfishing boat, designed for comfort, performance, and big catches. Outfitted with outriggers, downriggers, and the latest equipment, this vessel ensures a smooth, productive trip. There’s even a private toilet on board, making it ideal for families and longer adventures.
Depending on the season, you could reel in Blackfin Tuna, King Mackerel (Kingfish), Sailfish, Mahi Mahi, Wahoo, Grouper, Snapper, and more. Whether you prefer trolling the blue water, bottom fishing the reefs, or kite fishing for pelagics, Capt. Phil tailors each trip to your goals and skill level—perfect for experienced anglers or families seeking a fun day at sea.
Everything you need for success is included: rods, reels, tackle, and lures. If live bait is required, Capt. Phil will let you know whether you’ll be catching it during the trip. A helpful First Mate is always on board to assist, and a 10–20% tip is appreciated for their expertise and effort.
Fishing licenses are covered, so there’s no extra paperwork—just show up ready to fish! Some species may be subject to local size or bag limits, and Capt. Phil will guide you on what can be kept or released.
Families with kids are more than welcome! Check ahead for child-sized life vests or bring your own. Pack snacks, sunscreen (non-spray), and sunglasses to keep everyone happy and comfortable. Drinks are provided, and moderate alcohol consumption is allowed—just avoid glass bottles and hard liquor.
With stunning ocean views, expert guidance, and plenty of rod-bending action, this Key West fishing trip offers something for everyone—from seasoned anglers chasing trophy fish to families looking to create lasting memories on the water.
Book your adventure with High Line Charters and Captain Phil Leonard today, and discover why Key West is one of the top fishing destinations in the world. Whether it’s your first catch or your hundredth, you’re guaranteed a day of excitement, sun, and unforgettable memories on the water.
What's Included
This guide offers trips that you are able to take home your catch.
Your Guide has some important details about your trip with them.
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Read about the licensing details that is / is not covered in the below trips.
This guide offers trips with nature and wildlife views.
When you book your fishing trip, you will need to first put down a deposit to hold the reservation.
Show More
What's Included
This guide offers trips that you are able to take home your catch.
Your Guide has some important details about your trip with them.
Show More
Read about the licensing details that is / is not covered in the below trips.
This guide offers trips with nature and wildlife views.
When you book your fishing trip, you will need to first put down a deposit to hold the reservation.
Show More
Kick off your morning with a 4-hour Key West reef fishing trip targeting Snapper, Grouper, and more. Perfect for all skill levels, this guided charter includes all bait, tackle, and gear—just bring your enthusiasm and enjoy a fun, action-packed day on the water!
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Spend your afternoon on a 4-hour Key West reef fishing trip targeting Snapper, Grouper, and more. Ideal for all skill levels, this guided charter includes all bait, tackle, and gear—just bring your excitement for an action-filled day on the water!
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Experience a 6-hour Key West reef and wreck fishing trip targeting Snapper, Grouper, Amberjack, and more. Start on the reefs, then move to deeper wrecks for bigger game. All bait, tackle, and gear are included—just bring your crew for an action-packed afternoon!
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Enjoy a 6-hour Key West reef fishing trip targeting Snapper, Grouper, Porgy, and more. Explore productive reefs with all bait, tackle, and gear provided. Perfect for anglers of all skill levels—just show up and enjoy a morning of steady bites and quality catches!
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Enjoy an 8-hour Key West reef and wreck fishing trip. Start on the reefs targeting Snapper, Grouper, then head to wrecks for Amberjack, Barracuda, and more. All bait, tackle, and gear are included—just bring your essentials for an action-packed evening on the water!
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Experience a full-day Key West offshore fishing trip targeting Swordfish, Mahi, Wahoo, Tilefish, Grouper, and more. Troll, drop, and deep-sea fish with all bait, tackle, and gear included—just bring your energy for a big-game adventure on the water!
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Enjoy a full 8-hour Key West reef and wreck fishing trip targeting Snapper, Grouper, Amberjack, and more. Start on the reefs, then head to wrecks for bigger fish. All bait, tackle, and gear are included—just bring lunch, sunscreen, and your crew for a full day of action!
Pick Your Date
Sportfishing boats
Boat Type:
Boat Guest Capacity:
6
Boat Length:
39 ft
Manufacturer Name:
Key West
Model Year:
1980
Engine Manufacturer Name:
Yanmar
# of Engines:
2
Horsepower Per Engine:
1
Maximum Cruising Speed:
26
Features: Downriggers Bait Tank Outriggers Flybridge Fish Finder GPS Radar
This 39’ Key West sportfishing boat, fully restored in 2022, offers a smooth and powerful ride with twin Yanmar engines. Built for comfort and performance, it accommodates up to 6 guests—perfect for offshore fishing adventures in style and reliability.
Sportfishing boats
Boat Type:
Boat Guest Capacity:
6
Boat Length:
39 ft
Vehicle Details