High Line Charters
High Line Charters
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!
Customer reviews
Rating summary
Photos & videos by reviewers (4)
+1Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
May 31, 2025
6 Hour Trip – Shark (AM)
High Line Charters, An experience worth reliving.
Big props to Captain Phil and his first made Jake, they took great care of myself and five friends like we were family. They showed us some of the best fishing areas that Key West has to offer. a day of great fishing, story telling and memories that we will cherish throughout our lives. His boat was very stable on the ocean with plenty of cover for the hot sun and cool breezes on the upper deck, the captain provided ice cold water and we were able to bring some adult beverages aboard to celebrate our catch and the experience. I do recommend a long sleeve fishing shirt or rash guard with a hat because the key west sun will get the best of you if you’re not prepared. Also swing by the local Public deli and pick your self up a sandwich for the trip, I met two locals there and they took fantastic care of us making sure our sandwiches were packed for fishing. These are the little things that make for a perfect day of fishing. My biggest thanks again goes to Captain Phil and Jake. Already looking forward to my next adventure High Line Charters.
Big props to Captain Phil and his first made Jake, they took great care of myself and five friends like we were family. They showed...
Captain replied
Coconut Creek, Florida
Aug 29, 2025
4 Hour Trip – Reef (PM)
4 Hour PM reef trip
Our trip with Captain Phil and First Mate Russ was absolutely incredible! From the moment we stepped on the boat, they made us feel welcome and confident that we were in great hands. The boat was very clean and well-equipped, and both Phil and Russ clearly know these waters like the back of their hands. They put us right on the fish. Russ was funny and super helpful. Definitely recommend
Our trip with Captain Phil and First Mate Russ was absolutely incredible! From the moment we stepped on the boat, they made us...
Captain replied
Jun 1, 2025
4 Hour Trip – Reef (AM)
Great Captain Phil and Amazing First Mate Josh
They couldn’t be more accommodating to our desires, and worked with us to make a superb experience. Josh in particular was EVERYWHERE from baiting hooks to finding spots to teaching novices what to do to landing our catch
They couldn’t be more accommodating to our desires, and worked with us to make a superb experience. Josh in particular was EVERYWHERE...
Captain replied
Jun 9, 2025
4 Hour Trip – Reef (AM)
Great experience
Captain and Mate were very nice and accommodating. Made sure we had fun and everyone caught atleast one fish. Would definitely book with them again!
Captain and Mate were very nice and accommodating. Made sure we had fun and everyone caught atleast one fish. Would definitely...
Trip availability and prices
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Customer reviews
Rating summary
Photos & videos by reviewers (4)
+1Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
Experience:
Boat
Crew
Overall
High Line Charters, An experience worth reliving.
6 Hour Trip – Shark (AM) on May 31, 2025
Big props to Captain Phil and his first made Jake, they took great care of myself and five friends like we were family. They showed us some of the best fishing areas that Key West has to offer. a day of great fishing, story telling and memories that we will cherish throughout our lives. His boat was very stable on the ocean with plenty of cover for the hot sun and cool breezes on the upper deck, the captain provided ice cold water and we were able to bring some adult beverages aboard to celebrate our catch and the experience. I do recommend a long sleeve fishing shirt or rash guard with a hat because the key west sun will get the best of you if you’re not prepared. Also swing by the local Public deli and pick your self up a sandwich for the trip, I met two locals there and they took fantastic care of us making sure our sandwiches were packed for fishing. These are the little things that make for a perfect day of fishing. My biggest thanks again goes to Captain Phil and Jake. Already looking forward to my next adventure High Line Charters.
Big props to Captain Phil and his first made Jake, they took great care of myself and five friends like we were family. They showed us some of the best fishing areas that Key West has to offer. a day of great fishing, story telling and memories that we will cherish throughout our lives. His boat was very stable on the ocean with plenty of cover for the hot sun and cool breezes on the upper deck, the captain provided ice cold water and we were able to bring some adult beverages aboard to celebrate...
Coconut Creek, Florida
Experience:
Boat
Crew
Overall
4 Hour PM reef trip
4 Hour Trip – Reef (PM) on August 29, 2025
Our trip with Captain Phil and First Mate Russ was absolutely incredible! From the moment we stepped on the boat, they made us feel welcome and confident that we were in great hands. The boat was very clean and well-equipped, and both Phil and Russ clearly know these waters like the back of their hands. They put us right on the fish. Russ was funny and super helpful. Definitely recommend
Our trip with Captain Phil and First Mate Russ was absolutely incredible! From the moment we stepped on the boat, they made us feel welcome and confident that we were in great hands. The boat was very clean and well-equipped, and both Phil and Russ clearly know these waters like the back of their hands. They put us right on the fish. Russ was funny and super helpful. Definitely recommend
Experience:
Boat
Crew
Overall
Great Captain Phil and Amazing First Mate Josh
4 Hour Trip – Reef (AM) on June 1, 2025
They couldn’t be more accommodating to our desires, and worked with us to make a superb experience. Josh in particular was EVERYWHERE from baiting hooks to finding spots to teaching novices what to do to landing our catch
They couldn’t be more accommodating to our desires, and worked with us to make a superb experience. Josh in particular was EVERYWHERE from baiting hooks to finding spots to teaching novices what to do to landing our catch
Experience:
Boat
Crew
Overall
Great experience
4 Hour Trip – Reef (AM) on June 9, 2025
Captain and Mate were very nice and accommodating. Made sure we had fun and everyone caught atleast one fish. Would definitely book with them again!
Captain and Mate were very nice and accommodating. Made sure we had fun and everyone caught atleast one fish. Would definitely book with them again!
FAQs about High Line Charters
The fish you can target
What is the boat like?
