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Guides > Captain Emmanuel Silva

High Line Charters

Key West FL

Inshore Fishing
Offshore Fishing
High Line Charters
High Line Charters
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Your Captain

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Emmanuel Silva

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Territory

High Line Charters  Fishing Territory

High Line Charters

locationKey West FL


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Emmanuel Silva

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Activities

Inshore Fishing
Offshore Fishing

Emmanuel Silva, Captain at High Line Charters

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.

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Upcoming Availability

February 2026
March 2026

Fishing Techniques

JiggingTrolling FishingHeavy TackleLight TackleDeep Sea / Bottom FishingKite FishingDrift Boat Fishing

What's Included

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Keep your Catch

Keep your Catch

This guide offers trips that you are able to take home your catch.

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

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License

License

Read about the licensing details that is / is not covered in the below trips.

Nature / Wildlife Views

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

Show More

What's Included

Keep your Catch

Keep your Catch

This guide offers trips that you are able to take home your catch.

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

Show More

License

License

Read about the licensing details that is / is not covered in the below trips.

Nature / Wildlife Views

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

Show More

Trips Available with High Line Charters

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