Key West Backcountry Fishing

NEW 1 - 8 People 4 - 8 Hours From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin

About Your Trip

Water Type

Inshore, Nearshore, Flats

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather.

ShadowCaster is a locally rooted service specializing in shallow-water fishing throughout the Backcountry and flats of Key West. For more than two decades, our captains have committed themselves to studying the tides, wind patterns, seasonal migrations, and unique environments that make this fishery one of the most dynamic in the world.

We offer hands-on, light-tackle trips designed for anglers of all experience levels. Every outing is shaped by the conditions of the day and supported...

About Your Trip

ShadowCaster is a locally rooted service specializing in shallow-water fishing throughout the Backcountry and flats of Key West. For more than two decades, our captains have committed themselves to studying the tides, wind patterns, seasonal migrations, and unique environments that make this fishery one of the most dynamic in the world.

We offer hands-on, light-tackle trips designed for anglers of all experience levels. Every outing is shaped by the conditions of the day and supported
by a deep understanding of how fish move through these waters.

This isn’t just fishing—it’s a front-row seat to wild, unspoiled Florida Keys beauty. The area you’ll explore includes the Great White Heron and Key West National Wildlife Refuges, where the waters still look like they did hundreds of years ago.

Your main targets? The legendary "Big Three" of flats fishing:

🎯 Tarpon – explosive power and acrobatics

🎯 Permit – elusive, strong, and built for the chase

🎯 Bonefish – fast, ghost-like fighters that demand finesse

You’ll also encounter sharks, barracuda, snapper, and jacks along the way—there’s always something ready to put your skills to the test.

Captain John and his crew specialize in both light tackle and fly fishing, and they’re pros at customizing the trip to match your experience level. Whether you're chasing a personal best or just looking for fun in the sun, the team delivers expert instruction, local insight, and good vibes all day long.

You’ll fish aboard a sleek 22’ Pathfinder—a top-tier flats boat built for comfort, stealth, and performance. Outfitted with:

- T-Top sunshade for relief from the heat
- MinnKota trolling motor for quiet, shallow-water approaches
- Garmin electronics, Power Pole anchor, and a Fusion Bluetooth stereo
- 65qt cooler to keep your drinks cold and your catch fresh

All rods, reels, bait, tackle, and licenses are included, and your catch will be cleaned at the end of the trip. Just bring sunscreen, sunglasses, snacks, and a sense of adventure.

From glassy sandbars to mangrove-lined creeks, every cast out here is a shot at something unforgettable. Book now and experience Key West flats fishing with one of the best teams in the Keys!
Amenities

Water Type

Inshore, Nearshore, Flats

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Live Bait

Live bait is included for this trip.

Location

This guide can be flexible with the departure location.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Physicality

This trip requires an average level of physical activity.

Boat Restroom

No, this boat does not have a bathroom on board.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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Pricing Matrix

4 hours 6 hours 8 hours
1 Person
$750.00
$1,000.00
$1,300.00
2 People
$750.00
$1,000.00
$1,300.00
3 People
$750.00
$1,000.00
$1,300.00
4 People
$750.00
$1,000.00
$1,300.00
5 People (two boats)
$1,500.00
$2,000.00
$2,600.00
6 People (two boats)
$1,500.00
$2,000.00
$2,600.00
7 People (two boats)
$1,500.00
$2,000.00
$2,600.00
8 People (two boats)
$1,500.00
$2,000.00
$2,600.00
Pay 15% of the price as a deposit today, with the balance due on the day of the trip.

About Your Guide

Profile photo of Captain Experiences guide John

John S.

Outfitter
Talkative
Instructional
Beginner Oriented
Comfortable
Quality
Laid-back
ShadowCaster is a locally rooted guiding company specializing in shallow-water fishing throughout the Backcountry and flats of Key West. For more than two decades, our captains have committed themselves to studying the tides, wind patterns, seasonal migrations, and unique environments that make this fishery one of the most dynamic in the world.

We offer hands-on, light-tackle trips designed for anglers of all experience levels. Every outing is shaped by the conditions of the day and...

About Your Guide

Profile photo of Captain Experiences guide John

John S.

Outfitter
ShadowCaster is a locally rooted guiding company specializing in shallow-water fishing throughout the Backcountry and flats of Key West. For more than two decades, our captains have committed themselves to studying the tides, wind patterns, seasonal migrations, and unique environments that make this fishery one of the most dynamic in the world.

We offer hands-on, light-tackle trips designed for anglers of all experience levels. Every outing is shaped by the conditions of the day and supported by a deep understanding
of how fish move through these waters.

Captain Travis is a South Florida native with a sharp instinct for fish and a serious work ethic. He’s been on the water since childhood and is currently studying marine engineering—bringing both brain and brawn to the boat. Travis is all about maximizing your time and dialing in every detail to get you hooked up.
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Start Location & Lodging Options

Your guide can be flexible with your start location.
You can work with your guide after booking to set a more specific start location in the area.

About Your Boat

Boat photo for Key West Backcountry Fishing
Boat Type
Center Console
Boat Manufacturer
Pathfinder
Boat Length
22'
Boat Restroom
No

About Your Boat

Boat Type
Center Console
Boat Manufacturer
Pathfinder
Boat Length
22'
Boat Restroom
No
Additional Amenities
T-Top, Sunshade, Fusion Bluetooth Stereo, MinnKota Trolling Motor, Garmin Electronics, Power Pole, 65qt cooler
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Trip Details & Amenities

Water Type

Inshore, Nearshore, Flats

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Live Bait

Live bait is included for this trip.

Location

This guide can be flexible with the departure location.

Weather

You won't lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Physicality

This trip requires an average level of physical activity.

Boat Restroom

No, this boat does not have a bathroom on board.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Target Species

Color-coded seasonality below is based on .
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

Techniques

Everything Else to Know

Everything is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip.
You're all set! You don't need to buy a license for this trip.
This trip is managed by an outfitter. John will be your point of contact and you will go out with one of their guides.
We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).
Cancel for free up to 14 days before the trip and receive credit back to your account. Cancelling within 14 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.
In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

Recent Reviews of Captain Experiences

Ralph

Verified Review

Super fun. Everyone enjoyed. Nice family time.

Ralph

Verified Review

Super fun. Everyone enjoyed. Nice family time.
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Zachery

Verified Review

Good time!

Zachery

Verified Review

Good time!
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Thomas

Verified Review

Great time, great guide. Can’t wait for the next trip.

Thomas

Verified Review

Great time, great guide. Can’t wait for the next trip.
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Bill

Verified Review

Great day with a guide I highly recommend. Five stars

Bill

Verified Review

Great day with a guide I highly recommend. Five stars
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Todd

Verified Review

Unbelievable pleasureful experience, best guided trip we have EVER had.

Todd

Verified Review

Unbelievable pleasureful experience, best guided trip we have EVER had.
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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.
We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.
Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!
In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.
Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.
After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.
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