7 Trips Available

from

$850

Guides > Captain Emmanuel Silva

High Line Charters

Key West FL

High Line Charters
High Line Charters
Show All Images Show All Images
Guidesly Guarantee

Your Captain

guide pic

Emmanuel Silva

Loading experience...

Identity Verified

Territory

High Line Charters  Fishing Territory
Guides > Captain Emmanuel Silva

High Line Charters

locationKey West FL

Guidesly Guarantee

Your Captain

guide pic

Emmanuel Silva

Identity Verified

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.

Show more>

Upcoming Availability

October 2025
November 2025

Fishing Techniques

JiggingTrolling FishingHeavy TackleLight TackleDeep Sea / Bottom FishingKite FishingDrift Boat Fishing

What's Included

previousnext
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

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

Key West Reef Fishing Charter for Snapper & Grouper (AM)
Best Price Guarantee
Key West Reef Fishing Charter for Snapper & Grouper (AM)Top-Rated
Key West Reef Fishing Charter for Snapper & Grouper (AM)Instant Booking
Key West Reef Fishing Charter for Snapper & Grouper (AM)Fishing - Inshore
Key West Reef Fishing Charter for Snapper & Grouper (AM)

Sportfishing boats39'Key West Max 6 guests (base trip price includes 6 guests)

Key West Reef Fishing Charter for Snapper & Grouper (AM)

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!

Morning Trip

Key West Reef Fishing Charter for Snapper & Grouper (AM)Maximum 6 persons allowed
(base trip price includes 6 guests)
Key West Reef Fishing Charter for Snapper & Grouper (AM)4 Hours
Key West Reef Fishing Charter for Snapper & Grouper (AM)8:00 AM
$850

Pick Your Date

Loading...
Key West Reef Fishing Charter for Snapper & Grouper (PM)
Best Price Guarantee
Key West Reef Fishing Charter for Snapper & Grouper (PM)Top-Rated
Key West Reef Fishing Charter for Snapper & Grouper (PM)Instant Booking
Key West Reef Fishing Charter for Snapper & Grouper (PM)Fishing - Inshore
Key West Reef Fishing Charter for Snapper & Grouper (PM)

Sportfishing boats39'Key West Max 6 guests (base trip price includes 6 guests)

Key West Reef Fishing Charter for Snapper & Grouper (PM)

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!

Afternoon Trip

Key West Reef Fishing Charter for Snapper & Grouper (PM)Maximum 6 persons allowed
(base trip price includes 6 guests)
Key West Reef Fishing Charter for Snapper & Grouper (PM)4 Hours
Key West Reef Fishing Charter for Snapper & Grouper (PM)2:00 PM
$850

Pick Your Date

Loading...
Key West Reef and Wreck Fishing Charter
Key West Reef and Wreck Fishing CharterTop-Rated
Key West Reef and Wreck Fishing CharterInstant Booking
Key West Reef and Wreck Fishing CharterFishing - Inshore
Key West Reef and Wreck Fishing Charter

Sportfishing boats39'Key West Max 6 guests (base trip price includes 6 guests)

Key West Reef and Wreck Fishing Charter

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!

Afternoon Trip

Key West Reef and Wreck Fishing CharterMaximum 6 persons allowed
(base trip price includes 6 guests)
Key West Reef and Wreck Fishing Charter6 Hours
Key West Reef and Wreck Fishing Charter2:00 PM
$1,200

Pick Your Date

Loading...
Key West Reef Fishing Charter for Snapper & Grouper
Key West Reef Fishing Charter for Snapper & GrouperTop-Rated
Key West Reef Fishing Charter for Snapper & GrouperInstant Booking
Key West Reef Fishing Charter for Snapper & GrouperFishing - Inshore
Key West Reef Fishing Charter for Snapper & Grouper

Sportfishing boats39'Key West Max 6 guests (base trip price includes 6 guests)

Key West Reef Fishing Charter for Snapper & Grouper

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!

Morning Trip

Key West Reef Fishing Charter for Snapper & GrouperMaximum 6 persons allowed
(base trip price includes 6 guests)
Key West Reef Fishing Charter for Snapper & Grouper6 Hours
Key West Reef Fishing Charter for Snapper & Grouper8:00 AM
$1,250

Pick Your Date

Loading...
Key West Combo Reef & Wreck Fishing Charter
Key West Combo Reef & Wreck Fishing CharterTop-Rated
Key West Combo Reef & Wreck Fishing CharterInstant Booking
Key West Combo Reef & Wreck Fishing CharterFishing - Inshore
Key West Combo Reef & Wreck Fishing Charter

Sportfishing boats39'Key West Max 6 guests (base trip price includes 6 guests)

Key West Combo Reef & Wreck Fishing Charter

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!

Full Day Trip

Key West Combo Reef & Wreck Fishing CharterMaximum 6 persons allowed
(base trip price includes 6 guests)
Key West Combo Reef & Wreck Fishing Charter8 Hours
Key West Combo Reef & Wreck Fishing Charter1:00 PM
$1,550

Pick Your Date

Loading...
Key West Offshore Big Game Fishing Charter
Key West Offshore Big Game Fishing CharterTop-Rated
Key West Offshore Big Game Fishing CharterInstant Booking
Key West Offshore Big Game Fishing CharterFishing - Offshore
Key West Offshore Big Game Fishing Charter

Sportfishing boats39'Key West Max 6 guests (base trip price includes 6 guests)

Key West Offshore Big Game Fishing Charter

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!

Full Day Trip

Key West Offshore Big Game Fishing CharterMaximum 6 persons allowed
(base trip price includes 6 guests)
Key West Offshore Big Game Fishing Charter10 Hours
Key West Offshore Big Game Fishing Charter8:00 AM
$2,200

Pick Your Date

Loading...
Key West Guided Reef & Wreck Fishing Trip
Key West Guided Reef & Wreck Fishing TripTop-Rated
Key West Guided Reef & Wreck Fishing TripInstant Booking
Key West Guided Reef & Wreck Fishing TripFishing - Inshore
Key West Guided Reef & Wreck Fishing Trip

Sportfishing boats39'Key West Max 6 guests (base trip price includes 6 guests)

Key West Guided Reef & Wreck Fishing Trip

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!

Full Day Trip

Key West Guided Reef & Wreck Fishing TripMaximum 6 persons allowed
(base trip price includes 6 guests)
Key West Guided Reef & Wreck Fishing Trip8 Hours
Key West Guided Reef & Wreck Fishing Trip8:00 AM
$1,550

Pick Your Date

Loading...

Vehicle

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

High Line Charters  Key West Boat

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.

Boat

High Line Charters  Key West Boat image 0

Sportfishing boats

Boat Type:

Boat Guest Capacity:

6

Boat Length:

39 ft

Vehicle Details

FAQs about High Line Charters

Loading...