High Line Charters

4.7/5 (7 reviews)

State licensed

Eisenhower Drive Amber Jack Slip #2, Key West, FL 33040, United States–

High Line Charters

State licensed

4.7/5 (7 reviews)

Eisenhower Drive Amber Jack Slip #2

Key West, FL, United States

Trips & prices Targeted species Boat info What's biting What's included Contact captain

Trips & prices What's included Targeted species Boat info Reviews Contact captain

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!

Popular features

Fishing license

Live bait

You keep catch

Catch cleaning & filleting

Drinks

Popular features

Fishing license

Live bait

You keep catch

Catch cleaning & filleting

Drinks

Rating

4.7

7 reviews

4.0

Boat & equipment

5.0

Captain & crew

5.0

Fishing Experience

Anglers' gallery (5)

All reviews (7)

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Showing 1 – 5 of 7 reviews

Emmanuel Silva

Member since 2025

5.0

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

Reported catch:

Response from Captain

September 11, 2025

Thank you so much for the fantastic 5-star review! We’re thrilled to hear you had such a great afternoon on the reef with us. It’s always our goal to keep the rods bending and to make every trip both productive and fun. We’re glad you enjoyed the fishing, and the time spent on the water.

Russ and I appreciate you choosing us for your Key West adventure, and we’d be honored to have you back aboard anytime you’re ready for another trip. Tight lines until then!

— Captain Phil & First Mate Russ

Steven Sinders

Indiana, US

•

Member since 2026

4.3

Verified

Mackerel Time

8 Hour Trip – Reef & Wreck (AM) on February 22, 2026 • 6 adults

Had a great time, loved the Captain and Russell "first mate". Caught plenty of fish and they recommended Kaya restaurant to cook our fresh catch. That was some of the best fish I have ever eaten. Well done!!

Joon Suk Oh

Virginia, US

•

Member since 2025

4.7

Verified

Fishing with Robert

4 Hour Trip – Reef (AM) on January 3, 2026 • 3 adults

Mark Kupsc

Massachusetts, US

•

Member since 2025

5.0

Verified

Fishing with Robert

4 Hour Trip – Reef (PM) on November 25, 2025 • 2 adults • 1 child

Neville Logan

Arizona, US

•

Member since 2025

5.0

Verified

High Line Charters, An experience worth reliving.

6 Hour Trip – Shark (AM) on May 31, 2025 • 2 adults

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.

Response from Captain

June 2, 2025

Hey man, really appreciate you taking the time to leave such an awesome review! Jake and I had a great time with you and your crew—felt like we were all just old friends out for a day on the water. Glad the boat kept you cool and comfortable

Trip availability and prices

Trip Date:

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June 2026

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Group Size

2 adults • 0 children

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4 Hour Trip – Reef (AM)

FREE Cancellation 3 days notice

4 hour trip starts at 8:00 AM

US $850