High Line Charters 

Just listed 
 
State licensed
 Eisenhower Drive Amber Jack Slip #2, Key West, FL 33040, United States
 
State licensed
Just listed 
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Eisenhower Drive Amber Jack Slip #2
Key West, FL, United States

Get ready to make unforgettable memories in Key West with High Line Charters! Join Captain Phil Leonard, a seasoned local with years of fishing experience, and chase some of the most exciting fish these waters have to offer.

Depending on the season, you might reel in Blackfin Tuna, King Mackerel (Kingfish), Sailfish, Mahi Mahi, Wahoo, Grouper, Snapper, and more. Whether you’re looking to troll, bottom fish, or even try your hand at kite fishing, Capt. Phil has you covered.

Bringing the family? Kids are more than welcome on board! Just check ahead for child-sized life vests or bring your own. And don’t forget the snacks—keeping everyone happy and fueled up is key to a great day on the water!

You'll be fishing aboard a 39’ Key West sportfishing boat, built for both comfort and performance. It’s equipped with outriggers, downriggers, and all the must-haves for a successful trip. There’s even a toilet on board for added convenience.

No need to worry about gear—rods, reels, tackle, and lures are all provided. If live bait is needed, just ask ahead of time so you know if you’ll be catching it yourself. A First Mate will be on hand to assist, and a 10–20% tip is always appreciated for their hard work.

Your fishing license is included, so all you have to do is show up and be ready for an epic day on the water! Some fish may need to be released due to regulations, but Capt. Robert will keep you informed.

To make the most of your trip, bring sunscreen (non-spray), sunglasses, and plenty of bottled water. Drinks are provided on board, and while alcohol is allowed in moderation, please avoid glass bottles and hard liquor.

Now, hop aboard High Line Charters and let’s go fishing!

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Trip availability and prices

Trip Date:
Days:
Group Size:
Trip Date:
Days:
Group Size:
Trip Date:
Days:
Group Size:
Almost there...
4 Hour Trip – Sunset Inshore
FREE Cancellation 3 days notice
4 Hour Trip, starts at 4:00 PM
Price for up to 6 people
US $800 
4 Hour Trip – Reef (AM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $900 
4 Hour Trip – Reef (PM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 2:00 PM
Price for up to 6 people
US $900 
4 Hour Trip – Snapper Night
FREE Cancellation 3 days notice
4 Hour Trip, starts at 7:00 PM
Price for up to 6 people
US $900 
6 Hour Trip – Shark (AM)
FREE Cancellation 3 days notice
6 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $1,250 
6 Hour Trip – Reef & Wreck (PM)
FREE Cancellation 3 days notice
6 Hour Trip, starts at 2:00 PM
Price for up to 6 people
US $1,250 
6 Hour Trip – Reef (AM)
FREE Cancellation 3 days notice
6 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $1,300 
6 Hour Trip – Troll/Deep Drop (PM)
FREE Cancellation 3 days notice
6 Hour Trip, starts at 2:00 PM
Price for up to 6 people
US $1,300 
6 Hour Trip – Cubera/Mutton Night
FREE Cancellation 3 days notice
6 Hour Trip, starts at 7:00 PM
Price for up to 6 people
US $1,300 
8 Hour Trip – Reef & Wreck (AM)
FREE Cancellation 3 days notice
8 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $1,600 
8 Hour Trip – Reef & Wreck (PM)
FREE Cancellation 3 days notice
8 Hour Trip, starts at 1:00 PM
Price for up to 6 people
US $1,600 
10 Hour Trip – Swordfish/Trolling
FREE Cancellation 3 days notice
10 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $2,200 
There are 26 people looking at this charter.

FAQs about High Line Charters

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Sportfishing boats
Capacity
6 persons
Boat length
39 ft
Year built
1980
Restored in
2022
Boat manufacturer
Key West
Boat type
Sportfishing

Engine model
Yanmar
Powered by
2 x 1HP
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What’s biting in Key West right now

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Recent fishing reports


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