Bonefishing Key West

(5) In demand!
231 Margaret Street
Key West FL, United States

Bonefishing Key West offers professionally guided shallow water sight fishing on the beautiful flats off Key West, Florida. You cannot find a bigger expert or a more patient teacher than Captain Lenny Leonard if you are a beginner. He has been fishing these waters since he was a child and will teach you anything you need to know with a smile on his face, as he wants you to experience the joy of flats fishing.

Key West, Florida consists of miles upon miles of protected marine sanctuaries and flats waiting to be fished. These flats are home to fish species such as Tarpon, Bonefish, Permit, Barracuda and Blacktip Sharks. These are the species you will target on your fishing adventure.

You will fish aboard a 2014 Maverick Mirage HPX carbon fiber flats boat. This skiff is designed for flats fishing. It is very comfortable to fish from, and the technical hull is stealthy quiet which helps when stalking Bonefish in 10 inches of water. The skiff is dry and comfortable riding and plenty fast at 40 plus mph. The boat is equipped with all the safety equipment you may need, as well as an icebox for the food and drinks you bring on the trip.

Bonefishing Key West has a strict catch and release policy, and their Captain Lenny is a firm believer in the preservation of the Key West fisheries. He is also a member of Reef Relief, Florida Fish and Wildlife, Oceana, Key West Chamber of Commerce, and We practice Catch & Release.

Select date to see available trips and rates:

  • Private trip
    8 Hour Flats Trip
      FREE Cancellation 30 days notice
    8 hours trip, starts at 8:00 AM
    US$ 650
    up to 2 persons
    Targeted species are Permit, Bonefish, Barracuda and Blacktip Sharks. All tackle included. Fly tackle or spin tackle. We have a cooler with ice & bottled water. You will need to bring additional food & drink, hat, polarized sunglasses & sunscreen.
  • Private trip
    6 Hour Flats Trip
    In demand!
      FREE Cancellation 30 days notice
    6 hours trip, starts at 8:00 AM
    US$ 550
    up to 2 persons
    You will target Bonefish, Barracuda, Permit, and Blacktip Shark. All tackle is included: fly tackle or spin tackle. We have a cooler with ice & bottled water. You will need to bring additional food & drink, hat, polarized sunglasses & sunscreen.
  • Private trip
    Half day charter
      FREE Cancellation 30 days notice
    4 hours trip, starts at 8:00 AM
    US$ 450
    up to 2 persons
    Sight fishing the flats. If you have limited time or just wanna a little fishing adventure on your holiday.

About this listing

Targeted Species

Barracuda (Great)
Shark (Blacktip)


Boat Specs

Maverick HPX (Flats boat) originally built in 2014. Powered by a 90HP Yamaha engine, with a maximum cruising speed of 34 knots.

17 ft
2 persons

Types of Fishing

Flats Fishing
Backcountry Fishing

Fishing Techniques

Fly Fishing


Life Jackets
Ice Box
Life Jackets
Ice Box

Trip Includes

Rods, reels & tackle
Live Bait
Fishing License Included
Fly Fishing Equipment


FREE Cancellation
You can cancel or change your booking free of charge up to 30 days before the trip date.
Pickup not included
Transfer to/from departure site is not included in trip rates.
Catch and Release Allowed


Book with 15% deposit
When the captain confirms your trip, FishingBooker charges your credit card a 15% deposit to guarantee your reservation.
Pay remaining balance to captain
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:
American Express

When paying the remaining balance with a credit card, there is a 3.5% fee.

About the Captain

Lenny Leonard
Key West, Florida, United States
Member since December 2016
Captain Lenny has been fishing the Key West flats since he was a child and knows the best and most productive spots better than anyone else. He is a favorite among customers for his knowledge, his patience, excellent company, but above all his professionalism. He will work tirelessly to put you on fish and teach you all about fishing.
Response time: 14 hours
Response rate: 78%

Key West Fishing Calendar

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Customer Reviews

5 out of 5 stars from 5 reviews

5 stars
4 stars
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1 star

Captain Lenny took my son and I out on a fantastic fishing trip.  He really worked hard to put us on the fish and make sure that we had a great day.  My son is 13 and Captain Lenny was patient and helped him in every way possible to make it a great experience. Highly recommend.

Fished January 27, 2017
  • Boat
  • Crew
  • Overall

As an avid fly fisherman, Lenny and I have been tarpon fishing together a couple times a year for about 5 years. Lenny lives in Key West and fishes these waters all year long, which is key to knowing the fishery. Lenny can always find fish. When we first fished together I was a novice to saltwater and Lenny was exceptionally patient as I learned the sport. Lenny helps me to be a better angler and fly fisherman each trip. He is not only an excellent guide, but also a great guy to spend time on the water with. Lenny is very passionate about fishing, guiding, and always goes the extra mile. He gets just as excited to see and hook fish as I do. I cannot recommend Lenny enough.

Fished January 25, 2017
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  • Crew
  • Overall

I have fished with Captain Lenny Leonard many times over many years. I keep coming back because of his great attitude (attitude makes the difference) and also because he is great with kids. Lenny works hard from morning til night - sometimes we’ve stayed out even as the sun dips below the horizon. He is very well versed with flats fishing, channel fishing and even reef fishing, and I can’t ever recall coming back in at the end of the day thinking that he didn’t give 110%. give Lenny a try and you’ll be glad you did. -Charlie Polsky

Fished December 26, 2016
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  • Crew
  • Overall