Tails2sails light tackle charter fishing

Capt. Charles Donney Stock Island, FL Incorporated Licensed Insured

We provide a fun fishing experience for novice and experienced fishermen and their families.  From offshore, reef and inshore trips available. All charters are custom tailored to what you want to fish for; also, beach and snorkeling trips available.

Tails2Sails Charters out of Key West, Florida offers your group the light tackle sport fishing trip of a lifetime! Captain Chuck Donney is the owner and operator of this premier Key West fishing charter, and looks forward to guiding your group of six to a successful day of screaming reels!

Half day, 3/4 day, and full day trips are offered on the lovely 31’ Yellowfin Center Console. We get to the fishing grounds quickly with twin 250hp Suzuiki 4-stroke engines. The Yellowfin is known as being one of the best built fishing boats on the market offering dry, stable rides. We’re able to reach shallow waters as deep as 18” to catch bait, and also the deep waters of the ocean to catch the monster trophies. This clean and fast vessel really is the best boat for your fishing trip!

And the Captain at the helm is known for getting his customers on the fish! He’s been fishing these waters for years and years and knows where to go to find the fish. After spending hours diving the reefs of Key West, he has a good understanding of fish habits. Along with this experience, and fishing commercially for several years, Captain Chuck has unsurpassed knowledge of how and why, when and where the fish bite. Regardless of your fishing skill, he is passionate about hooking you up with the “big one”!

Each trip is unique, and Tails2Sails Charters is happy to accommodate your perfect Key West fishing trip. Provided in the cost of the trip is your rod, reels, lures, bait and fishing license. All rods are custom made, from ultra-light to heavy stand-ups. All spinning reels are Van Steal. Stand ups are Penn and Shimano. You’ll want to bring any food or drinks, sunscreen/sunprotection (such as hats or visors), and of course your camera.

Tails2Sails also provides sandbar and beach trips to go swimming after fishing. Snorkeling equipment is provided for those who would like to discover the beauty of Florida Reefs. Captain Chuck is happy to take you any time during the trip!

For a memorable Key West fishing trip, book with Captain Chuck and Tails2Sails Charters! See you on the water!

833-I-GO-FISH (446-3474)

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  Launch Location

5130 U.S. 1, Stock Island

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Trips start at $650

3 Trips

1-6 guests

See available trips

2003 31' Center Console

250 HP engine(s)

  • GPS
  • Fishfinder
  • Children Welcome
  • Clients Keep Catch
  • No Illegal Substances



Select an Available Trip



Includes 6 guests

Trip time: 8:00am to 12:00pm (4 hours)

3 Day Cancellation Policy

Half Day Charter
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Includes 6 guests

Trip time: 8:00am to 2:00pm (6 hours)

3 Day Cancellation Policy

Custom charters .

Close details



Includes 6 guests

Trip time: 8:00am to 4:00pm (8 hours)

3 Day Cancellation Policy

Full Day Charter
Close details

Fish Species

Black Grouper
King Mackerel
Mahi Mahi
Mangrove Snapper
Mutton Snapper
Red Grouper

Additional Details

Safety Features

  • Life Jackets
  • Fire Extinguishers
  • First-Aid Equipment
  • CPR-Trained Crew
  • Flares
  • VHF Radio


  • GPS
  • Fishfinder

Boat Features

  • Cooler
  • Multimedia System

Boat Gear

  • Casting Platform
  • Downriggers
  • Livewell
  • Spearfishing Equipment
  • Snorkeling Equipment

Fishing Techniques

  • Bottom Fishing
  • Bow Fishing
  • Deep Sea Fishing
  • Drift Fishing
  • Jigging
  • Kite Fishing
  • Light Tackle
  • Spearfishing
  • Spinning
  • Trolling

Fishing Policies

  • Children Welcome
  • Clients Keep Catch
  • No Illegal Substances

Price Includes

  • Catch Cleaning & Filleting
  • Fishing License
  • Fly Fishing Equipment
  • Fresh or Live Bait
  • Lures
  • Rods, Reels & Terminal Tackle
  • We also do sandbar and beach trips
  • dolphin watching
  • and snorkeling charters

Minimum Age

  • All ages welcome

Fishing Location

  • Backcountry
  • Inshore
  • Nearshore
  • Offshore
  • Reef
  • Wreck

About the Vessel


Capt. Charles Donney

Boat Type

Center Console

Boat Length


Year Built


Engine Manufacturer

Suzuki 250

Number of Engines


Engine Horsepower

250 HP