High Line Charters
+14Get 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!
Charter Operator
High Line Charters
Most popular features:
Trip availability and prices
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...
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
FAQs about High Line Charters
What are the trip rates for High Line Charters?
High Line Charters offers the following trips to customers:
- US $800 per group - 4 Hour Trip – Sunset Inshore (4 hours)
- US $900 per group - 4 Hour Trip – Reef (AM) (4 hours)
- US $900 per group - 4 Hour Trip – Reef (PM) (4 hours)
- US $900 per group - 4 Hour Trip – Snapper Night (4 hours)
- US $1,250 per group - 6 Hour Trip – Reef & Wreck (PM) (6 hours)
- US $1,250 per group - 6 Hour Trip – Shark (AM) (6 hours)
- US $1,300 per group - 6 Hour Trip – Cubera/Mutton Night (6 hours)
- US $1,300 per group - 6 Hour Trip – Reef (AM) (6 hours)
- US $1,300 per group - 6 Hour Trip – Troll/Deep Drop (PM) (6 hours)
- US $1,600 per group - 8 Hour Trip – Reef & Wreck (AM) (8 hours)
- US $1,600 per group - 8 Hour Trip – Reef & Wreck (PM) (8 hours)
- US $2,200 per group - 10 Hour Trip – Swordfish/Trolling (10 hours)
Which amenities are available onboard with High Line Charters?
When you book a trip with High Line Charters, you can expect the following amenities onboard:
- Toilet
- GPS All Equipment is brand new top & top of the line
- Fishfinder
- Flybridge
- Multimedia System JL Audio Speakers & All Brand new audio
- Outriggers
- Ice Box for fish & Extra Coolers for Food/Drinks
- Radar
What's included in the trip price with High Line Charters?
Trips booked with High Line Charters include:
- Rods, reels & tackle
- Live Bait
- Lures
- Catch cleaning & filleting
- Drinks (Water Provided additional drinks on request)
- First Mate
- Fishing License
What types of fishing does High Line Charters offer?
High Line Charters offers the following types of fishing:
- Inshore Fishing
- Offshore Fishing
- Reef Fishing
- Wreck Fishing
What fishing techniques does High Line Charters offer?
High Line Charters offers the following fishing techniques:
- Light Tackle
- Heavy Tackle
- Bottom Fishing
- Trolling
- Spinning
- Jigging
- Drift Fishing
- Kite Fishing
- Deep Sea Fishing
Which fish species can I catch with High Line Charters?
Top targeted fish species with High Line Charters include:
- Dolphin (Mahi Mahi)
- Grouper (Black)
- Grouper (Red)
- King Mackerel (Kingfish)
- Sailfish
- Snapper (Mangrove)
- Snapper (Mutton)
- Snapper (Yellowtail)
- Tuna (Blackfin)
- Wahoo
Your operator
Key West, Florida, United States
Our love for fishing started when we were all just kids, but it truly came alive out on the clear blue waters of Key West, Florida. The ocean here is full of life, adventure, and excitement, and I’ve spent years learning its every current, reef, and hidden hotspot. Whether it’s chasing schools of Mahi-Mahi near floating seaweed or battling the powerful wahoo as it streaks through the water like a torpedo, there’s nothing like fishing in the Florida Keys. I still remember the first time I hooked into a sailfish—its silver body leaping high above the waves, the reel screaming as it ran. Those moments make your heart pound and leave you with stories you’ll tell forever. From Blackfin Tuna that fight like champions to the thrill of landing a prized wahoo, every day out here brings a new challenge and a new reward. Now, running our own fishing charter company in Key West lets me share that excitement with others. These waters have become our second home, and we know them like the back of our hands. We love taking people out to chase their dream fish, whether it’s their first time on a boat or they’re seasoned anglers looking for the next big catch. Watching someone reel in their first Mahi or feeling the rush of a tuna on the line never gets old. Out here, it’s more than just fishing—it’s about the thrill of the hunt, the beauty of the ocean, and the memories you take back to shore. Our goal is to give every person who steps on the High Line the chance to experience the magic of Key West fishing and leave with a story they’ll always remember.
The fish you can target
What is the boat like?
What kind of fishing will you do?
Inshore Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing
Which fishing techniques you can try
Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Spinning
Jigging
Drift Fishing
Kite Fishing
Deep Sea Fishing
Which amenities are available onboard
Toilet
GPS
All Equipment is brand new top & top of the line
Fishfinder
Flybridge
Multimedia System
JL Audio Speakers & All Brand new audio
Outriggers
Ice Box
for fish & Extra Coolers for Food/Drinks
Radar
What’s included in the trip price
Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Drinks
Water Provided additional drinks on request
First Mate
Fishing License
How cancellations work
Free cancellation up to 3 days prior to trip
You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
What the listing policies are
Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
You Keep Catch
Catch and Release Allowed
How you can pay
Book with 15% deposit, pay rest to captain
When the captain confirms your trip, FishingBooker charges your credit card a 15% deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Visa
Mastercard
American Express
PayPal
Bank Transfer
When paying the remaining balance with a credit card, an additional 2.5% charge will apply.
What’s biting in Key West right now
Dolphin (Mahi Mahi)
Grouper (Black)
Grouper (Red)
King Mackerel (Kingfish)
Sailfish
Snapper (Mangrove)
Snapper (Mutton)
Snapper (Yellowtail)
Tuna (Blackfin)
Wahoo