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Captain Chuck Donney - "Tails 2 Sails"

Captain Chuck has been fishing the waters of Key West and the Marquesas since he was in high school here in Key West. As a youngster, he spent three years in the Philippines diving and spear fishing - practically living on the coral reef. In Key West he learned where to go and how to catch the fish before high tech navigation. Chuck lives to fish, so much so that, he decided to make it his occupation.

Captain Chuck spent countless hours diving on the reefs in the Far East and off Key West , observing how fish behave and learning which bait works best which fish in which conditions. That experience along with fishing commercially for past ten seasons has really given him a deep understanding of how and why, when and where the fish bite . Captain Chuck's true passion is to be out on the water, putting people on fish and seeing how excited they get when hooked up with their "big one"! Chuck has guided hundreds of anglers, from novice to expert, to trophy catches. Captain Chucks goal is your complete satisfaction. Regardless of your fishing skill level, Captain Chuck is completely dedicated to making your charter fishing trip with Tails2Sails the experience of a lifetime.

Captain Chuck runs the beautiful Tails 2 Sails, a state-of-the-art 31' Yellowfin center console, light tackle fishing machine. Yellowfin has long been known for being the absolute best built boat on the market. She has a 9'6" beam for a dry, stable ride and draws only 18", making her perfect for catching bait in shallow water. She is outfitted with the latest state-of-the-art electronics, Fully enclosed vacuum head, a custom built coffin fish box, Twin high volume live wells (25 & 65gal.) and powered with twin 250hp Suzuki 4-stroke engines. She's the perfect blend of comfort and speed. The Tails 2 Sails will get you there fast, dry and safe....welcome aboard!

    Boat Information
  • Twin 250hp Suzuki 4-stroke engines
  • 235 Gallon fuel tank (range over 500 miles)
  • High Performance K-PLANES
  • Oversized T-top for plenty of shade!
  • 530qt. macerated in deck Fish Box
  • 410qt. Coffin fish Box
  • Large custom built console cooler
  • Garmin 3210c GPS/ Chartplotter w/ XM Nexrad
  • Furuno 565 Digital color depth recorder
  • Garmin GMR 18 4kw X-band Digital Radar
  • Icom 502 VHF & Icom 504 VHF
  • Raytheon 220 VHF
  • JVC AM/FM/CD Stereo


Capt. Chuck Donney
My team mates and I had the pleasure of fishing with Capt. Chuck during our fishing club's annual Key West tournament May 19. Capt. Chuck communicated well prior to the tournament. He developed the strategy for the day based on the tournament point schedule and was prepared the morning of the tournament with appropriate bait, tackle, knowledge of fish location, tides and current, and our team won!! He was also an excellent coach, not only for getting our multitude of different fished hooked up, but in getting them to the boat. Many thanks for a fun and successful day. Everyone on the team agreed that we would welcome the opportunity to fish with Capt. Chuck again.

Larry C
Lighthouse Point


Best Charter Fishing in 25 Years for the Corrado Brothers !!
My brothers, Vincent, Charles, and Myself have been fishing for over 25 years. We have fished Costa Rica, the Upper Keys, Destin Florida, and all up and down the west coast. 

We fished April 2nd, 4th, and 6th with Capt. Chuck Donney on his "Tails 2 Sails" for 3 of the best days of fishing anyone could ask for. Chuck's 31 Yellowfin CC equipped with the best tackle, along with his professional and "great" people person skills resulted in us catching over 16 species of fish, which of 9 were kept for our "fresh catch" with 104 fish safely released. The highlight of the trip was Me watching my brothers Vincent and Charles catching their first Tarpon. We will be contacting Capt. Al Ristori who writes a weekly salt water fishing report in the New Jersey Star Ledger, the largest statewide paper in New Jersey, and have him mention Key West Pro Guides in his column. One thing that the Corrados will promise, WE WILL RETURN !! next year!! Capt. Paul, Capt. Roc, and or course our "Man of the Year" Capt. Chuck Donney..... Thank You!!

"Tightlines", Rob Corrado.. Scotch Plains, New Jersey.


Tails 2 Sails Delivers!
We caught 11 Mutton Snapper each 12-15lbs each and 4 Porgy around 10lbs ea!
We had on, but lost (we were using lightweight tackle), a sail fish, and what we suspect where 2 sharks and a Goliath Grouper. Capt chuck really understands the finesse aspects of fishing that make him IMHO, a great guide. It is fishing (not catching) and I have fished enough charters to know this was an exceptional day, however without Chuck's skill & knowledge we wouldn't have caught a fraction of what we did. All day long we heard other boats on the radio struggling to put fish in the boat while our action was non stop and we caught HUGE fish. We had fun and I will only book with Chuck going forward.

Toronto, Canada

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