Heads or Tails Fishing 

5.0/5 (1 review)
 
State licensed
 Intracoastal Circle, Jacksonville, FL 32233, United States

Heads or Tails Fishing 

Up to 3 miles
Jacksonville, FL, United States
16 ft
3
5.0/5 (1 review)

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Join Heads or Tails Fishing for an unforgettable inshore adventure in Jacksonville, Florida!

Guided by Captain Harry Ware, an experienced fly fishing guide with nearly a decade of professional experience in the Rocky Mountain West, you'll explore the scenic marshes, creeks, and flats of Northeast Florida targeting Redfish, Trout, and more.

Capt. Harry specializes in fly fishing and casting instruction, offering expert guidance for anglers of all skill levels. Whether you're chasing tailing Reds on the fly or learning to make your first perfect cast, each trip is designed to be educational, fun, and rewarding.

Prefer spinning gear? Light tackle and live bait options are always available for those who want a more traditional approach or to mix it up throughout the day. With a focus on teaching, conservation, and a great time on the water, Heads or Tails Fishing delivers a first-class experience for every guest.

Book your trip today and discover Jacksonville's incredible inshore fishery.

Join Heads or Tails Fishing for an unforgettable inshore adventure in Jacksonville, Florida!

Guided by Captain Harry Ware, an experienced fly fishing guide with nearly a decade of professional experience in the Rocky Mountain West, you'll explore the scenic marshes, creeks, and flats of Northeast Florida targeting Redfish, Trout, and more.

Capt. Harry specializes in fly fishing and casting instruction, offering expert guidance for anglers of all skill levels. Whether you're chasing tailing Reds on the fly or learning to make your first perfect cast, each trip is designed to be educational, fun, and rewarding.

Prefer spinning gear? Light tackle and live bait options are always available for those who want a more traditional approach or to mix it up throughout the day. With a focus on teaching, conservation, and a great time on the water, Heads or Tails Fishing delivers a first-class experience for every guest.

Book your trip today and discover Jacksonville's incredible inshore fishery.

Harry Ware
Captain
Harry Ware
9 years of experience
ID & credentials verified

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
August 2026
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Number of days
1
Group Size
2 adults • 0 children
Change
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Half Day Trip
FREE Cancellation 3 days notice
4 hour trip starts at 8:00 AM
Redfish
Flounder
Speckled Trout
US $500
Entire boat: up to 3 people
Full Day Trip
FREE Cancellation 3 days notice
8 hour trip starts at 7:00 AM
Redfish
Flounder
Sheepshead
Speckled Trout
US $900
Entire boat: up to 3 people

Customer reviews

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Rating

5.0
1 review
5.0
Boat & equipment
5.0
Captain & crew
5.0
Fishing Experience

All reviews (1)

Frequently mentioned
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Showing 11 of 1 review
Roger Schmidt
Roger Schmidt
us
Illinois, US
Member since 2025
5.0
Verified
Went out of his way to help me catch redfish
Half Day Trip on May 20, 20261 adult

At the beginning, the Fish warrant biting but it changed and we were able to catch three nice fish well worth the trip. I do it again and captain was very nice. I really liked him.

FAQs about Heads or Tails Fishing

Heads or Tails Fishing offers the following trips to customers:
  • US $500 per group - Half Day Trip (4 hours)
  • US $900 per group - Full Day Trip (8 hours)
When you book a trip with Heads or Tails Fishing, you can expect the following amenities onboard:
  • GPS
  • Live bait well
  • Wireless trolling motor
  • Ice box
Trips booked with Heads or Tails Fishing include:
  • Rods, reels & tackle
  • Lures
  • Catch cleaning & filleting (Yes)
  • Drinks (Water will be provided)
  • Fishing license (Your license is included with the trip. )
  • Fly fishing equipment
Heads or Tails Fishing offers the following types of fishing:
  • Inshore fishing
  • Nearshore fishing
  • Flats fishing
Heads or Tails Fishing offers the following fishing techniques:
  • Light tackle
  • Spinning
  • Fly fishing
Top targeted fish species with Heads or Tails Fishing include:
  • Flounder
  • Redfish
  • Sheepshead
  • Speckled Trout

Your captain

Harry Ware
Harry Ware
Harry Ware

Jacksonville, Florida, United States

1 Fishing Report
ID & license verified
1 Customer review
Typical response within 1 hour
Member since October 2025

Capt. Harry Ware is your guide to an unforgettable fishing adventure in the waters of Jacksonville, Florida. Explore these waters teeming with Sheepshead, Speckled Trout and Flounder under Harry's expert guidance. The only way to learn is to join them on the water.

1 Fishing Report
ID & license verified
1 Customer review
Typical response within 1 hour
Member since October 2025

Capt. Harry Ware is your guide to an unforgettable fishing adventure in the waters of Jacksonville, Florida. Explore these waters teeming with Sheepshead, Speckled Trout and Flounder under Harry's expert guidance. The only way to learn is to join them on the water.

The fish you can target

Flounder
Flounder
Redfish
Redfish
Sheepshead
Sheepshead
Speckled Trout
Speckled Trout
Flounder
Flounder
Redfish
Redfish
Sheepshead
Sheepshead
Speckled Trout
Speckled Trout

Real catches by this captain

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What is the boat like?

Boat image
Boat category
Skiffs and flats boats
Capacity
3 persons
Boat length
16 ft
Year built
2001
Restored in
2019
Boat manufacturer
Hell’s Bay
Boat type
Flats boat
Engine model
Suzuki
Powered by
1 x 60HP
Max cruising speed
33 knots

What kind of fishing will you do?

Inshore Fishing
Nearshore Fishing
Flats Fishing

Which fishing techniques you can try

Light Tackle
Spinning
Fly Fishing

Which amenities are available onboard

GPS
Live bait well
Wireless trolling motor
Ice box
What's included in the trip price
Rods, reels & tackle
Lures
Catch cleaning & filleting
Yes
Drinks
Water will be provided
Fishing license
Your license is included with the trip.
Fly fishing equipment

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.

More details

What the listing policies are

Pickup agreed upon reservation

Transfer to/from departure site may be available and included in price depending on your location and distance from the dock.

You keep catch
Catch and release allowed

How you can pay

Book with 30% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 30% 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

 Bank transfer

What’s biting in Jacksonville right now

RedfishRedfish
Speckled TroutSpeckled Trout

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