Name: HighLine Charters
Address: Key West, FL
Price range: $850 - $1550

About Your Guide

Phil Leonard

Independent Guide

Veteran

Talkative

Laid-back

Instructional

Beginner Oriented

Quality

Adventurous

Hi, I’m Captain Phil! I’ve been fishing the waters around Key West for a long time, and I love helping people have an amazing time on the ocean. I take families, friends, and first-time anglers out to catch fish, enjoy the sunshine, and make great memories. My boat is safe, clean, and has plenty of space to relax. You’ll also meet Jake, my awesome first mate—he’s super helpful and great with kids and beginners. We’ll help you with everything—from baiting your hook to reeling in your catch. I know where the fish like to hide and will do my best to put you on them. Whether you're here for fun or hoping to land a big one, we’ll make sure it’s a trip to remember!

About Your Guide

Phil Leonard

Independent Guide

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Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?

The biggest fish I’ve caught was a giant grouper that weighed over 200 pounds. It took everything I had!!! I’ll never forget that one.

If you were cooking for all your friends what would you cook?

FISH!!!

What’s your favorite band?

Metallica, Earth, Wind & Fire

What’s your favorite movie?

Jaws

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?

The biggest fish I’ve caught was a giant grouper that weighed over 200 pounds. It took everything I had!!! I’ll never forget that one.

If you were cooking for all your friends what would you cook?

FISH!!!

What’s your favorite band?

Metallica, Earth, Wind & Fire

What’s your favorite movie?

Jaws

What’s your favorite sports team?

Yankees!!!

What’s your drink of choice?

Whiskey & water

What was your last halloween costume?

Ace Ventura

What do you want for Christmas this year?

Crocs

How did you get started guiding?

I’ve been fishing most of my life and always loved being on the water. Friends and family started asking me to take them out. Before long, guiding charters just felt like the right path—and I’ve been doing it ever since.

What makes you different from other guides?

I treat every trip like it’s the most important one of the season. It’s not just about catching fish—it’s about making sure you have fun and feel taken care of. With me and Jake, you’re not just a customer, you’re part of the crew.

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