Tails 2 Sails Charters Fishing

Head out with Tails 2 Sails Charters Fishing and explore one of the most famous fishing destinations in the world! Captain Charles Donney is a light tackle fishing expert and Key West, Florida is his personal playground. This local pro knows all the spots, tips, and tricks to get you on high quality eating fish, as well as game fish trophies.

Hop aboard a 31’ Yellowfin sportfishing center console. She can comfortably accommodate up to 6 guests, with 3–4 anglers able to fish at the same time. She’s equipped with GPS and Fishfinder to help you find your targets, and a live well and ice box to keep your bait and catch fresh.

Whether you choose to stay inshore or you decide to venture into deep waters, you’ll be targeting some of Southern Florida’s most famous fish. Closer to the dock you’ll hook into Mutton and Mangrove Snapper, Tarpon, and Little Tunny.

Offshore, it’s all about Red Snapper, majestic Sailfish, quick Wahoo, delicious Mahi Mahi, and Skipjack Tuna. Your captain provides all the gear you need for a great catch including custom rods, Fin Ors, and Penn reels. Live bait, lures, and catch cleaning are also included.

Bring along any drinks and snacks you’d like to enjoy – just leave the hard liquor at home. All that’s left to do is lather on some sunscreen and head out!

Experience this iconic fishery with a local pro aboard Tails 2 Sails Charters Fishing!



Select date to see available trips and rates:

  • Private trip
    Full Day Trip
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 8:00 AM
    $1,000
    price breakdown
    $1,000
    To really make the most out of your Key West fishing experience, head out on this 8-hour adventure! If you're hoping to hook majestic Sailfish or reel in delicious Red Snapper and Mahi Mahi – this is the trip to choose. Capt. Charles customizes each trip to your needs and brings along all the gear, live bait, and lures you need. Bring enough drinks and snacks to keep you going and you're all set!
  • Private trip
    3/4 Day Trip
    FREE Cancellation 3 days notice
    6 Hour Trip, starts at 8:00 AM
    $850
    price breakdown
    $850
    Give yourself some extra time on the water and explore Key West on this 6-hour trip! Whether you want to stay inshore and target big Tarpon or head into the reefs for some bottom fishing, Capt. Charles sets up the trip to your wishes. He'll bring along all the gear, live bait, and lures you need. Feel free to bring along a cooler with drinks and snacks – just leave the hard liquor at home.
  • Private trip
    Half Day Trip (AM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    $700
    price breakdown
    $700
    Head out for 4 hours of fishing in Key West, Florida! Capt. Charles will customize your trip based on what you're targeting and set up the boat for maximum efficiency. You decide what you want to target and he'll construct a plan to make it happen! Gear, lures, live bait, and water bottles are included. Feel free to bring along any other soft drinks and snacks you'd like.
  • Private trip
    Half Day Trip (PM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 1:00 PM
    $700
    price breakdown
    $700
    Prefer to get out in the afternoon instead? Not a problem! This 4-hour trip is yours to customize. Get in touch with Capt. Charles beforehand, tell him what you want to target. He'll set up the boat accordingly and create a plan of action. All you'll want to bring are any soft drinks and snacks you'd like you to enjoy. He'll take care of the gear, lures, and live bait.
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About the Captain

Charles Donney
Stock Island, Florida, United States
2 Customer Reviews
Response time within an hour
Member since February 2020
Hi, I'm Charles Donney. Owner, captain, and boat washer of Tails 2 Sails Charters located in Key West, FL. I offer fishing charters on my 31' Yellowfin sportfishing center console. I specialize in light tackle fishing for many of the most popular game fish in South Florida. Everything from the high quality eating fish, such as Snapper and Grouper, to Tarpon inshore and Mahi Mahi and Sailfish offshore. I'm a big fan of taking kids fishing, these are some of the best memories you can make! As far as me, I've finished high school here in the early '90s and traveling for a while before making Key West my home. I've been chartering for almost 20 years on a variety of different boats before heading out on my own. I've been running Tails 2 Sails now for 10 years now have completed thousands of charters. Every day is different and lots of fun! You never know what you're going to catch or see on the water in the Keys. Its what keeps me going – that and the gas money!

About this listing

Targeted Species

Amberjack Amberjack
Cobia Cobia
Dolphin (Mahi Mahi) Dolphin (Mahi Mahi)
King Mackerel (Kingfish) King Mackerel (Kingfish)

Little Tunny (False Albacore) Little Tunny (False Albacore)
Sailfish Sailfish
Snapper (Mangrove) Snapper (Mangrove)
Snapper (Mutton) Snapper (Mutton)

Snapper (Red) Snapper (Red)
Tarpon Tarpon
Tuna (Skipjack) Tuna (Skipjack)
Wahoo Wahoo

Boat Specs

Yellowfin (Center console) originally built in 2002. Powered by 2 250HP Suzuki 250 engines.

Length
31 ft
Capacity
6 persons

Types of Fishing

Inshore Fishing
Nearshore Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing

Fishing Techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Spinning
Jigging
Drift Fishing
Kite Fishing
Deep Sea Fishing

Amenities

GPS
Fishfinder
Live Bait Well
Ice Box
GPS
Fishfinder
Live Bait Well
Ice Box

Trip Includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Drinks
Fishing License

Cancellation Policy

Free cancellation up to 3 days prior to trip

Customers can cancel or modify their booking up to 3 days before the trip date free of charge. If the trip is canceled or modified later, or in the event of a no-show, 100% of the deposit will be charged.

Listing Policies

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
You Keep Catch
Catch and Release Allowed

Payment

Book with 20% deposit
When the captain confirms your trip, FishingBooker charges your credit card a 20% 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:
Cash
Visa
Mastercard
American Express

Stock Island Fishing Calendar

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Customer Reviews

Rating Summary
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out of 5 stars from 2 reviews
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Angler Rating
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0%
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James d.

The captain canceled

VERIFIED   December 12, 2020
The charter operator canceled on trip date. This is an automated posting
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Mike S. C.
Lake In The Hills, IL
Poor Poor Poor Poor Poor  1.00
Experience:
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Fishing with Charles

VERIFIED   3/4 Day Trip on December 11, 2020
The captain was not there when we showed up
Mike S. C. does not recommend Tails 2 Sails Charters Fishing
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  Charles Donney Captain replied