Welcome to the newest and best sailing school in tampa bay

Captain Doran is rated the #2 ASA Instructor in the world-wide system of 2400+ instructors. He has been “Instructor of the Year” the past four years. He has been ASA and USCG Master certified since 2002.

Captain Doran comes from a cruising and racing background having sailed his own boat from California to Florida (through the Panama Canal). He has won multiple national sailing championships on monohulls and multihulls. After a successful corporate career Captain Doran launched a regional sailing magazine – Southwinds – as publisher and editor for 10 years while also covering sailing for the St. Petersburg Times, Sail, Sailing World, and other sailing media. 

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Captain Doran
Captain Doran
CEO Founder

Tampa Bay Sailing School will be offering a series of American Sailing Association certifications – 101, 103, 104, 105,106, and 114. Teaching is conducted on an O’day 30 with diesel inboard, wheel steering, autopilot, and full instrumentation including GPS at the helm. 

Come join us…it is a life-changing experience…with the top instructor based on student ratings. 

American Sailing
American Sailing Association
American Sailing Certified
Results Oriented

What Students Are Saying

Tampa Bay Sailing School

I just finished ASA 101 with Capt. Doran and it was excellent! Learned a ton, got some great hands-on sailing practice, and Doran was super friendly and engaging. Would highly recommend.

Alex Brikett
Tampa Bay Sailing School

We thoroughly enjoyed our sailing lesson with Captain Doran on the Boomerang. We got to practice many drills, maneuvers, and techniques even in light wind. It was a wonderful and fulfilling experience.

Tampa Bay Sailing School

Capt. Doran is a pro, easy to get to know, and most of all a fantastic instructor. We had two great days on the water, and I am looking forward to 103 and beyond. These guys are top notch!

James Long

How I Fell in Love with Sailing

ASA Instructor, Doran Cushing, on falling in love with sailing:

We had no boats growing up. My Dad “thrilled” me by taking us to the beach for surf casting….throw some bait in the surf, sit back…drink a Falstaff or two. That was my “nautical” background. 

Fast forward to the 80’s. I’m working at Disney in Burbank, California but owned a house in Redondo Beach…5 freeways from work. So I decided to move to the San Fernando Valley and find a roommate. 

Enter Jim. He owned a little beach cat but knew NOTHING about sailing. So he decided that us guys would charter a 37’ Erickson…with our lady friends… and sail 42 miles out in the Pacific Ocean to Santa Barbara Island.

Catalina was 22 miles or so but no…three novice sailors HAD to go to a pimple in the ocean.

Phase One. I have no idea how Jim got the boat. 

Phase Two. With full main and genny, we’re off and blasting through the seas close-hauled. 

Phase Three. With people turning green and the rail underwater we lose the jib halyard 20 miles out of Marina del Oz. Shackle was overloaded and the sail goes into the ocean. Bob goes forward to retrieve the sail. Jim is at the helm and he suddenly loses steerage.

Phase Four. With all the rocking and rolling we were doing in the rough seas the oars for the inflatable dinghy which was stored in the cockpit lazaret…Well, the oars got into the steering quadrant and knocked the cables off. 

So we find the emergency tiller. How Jim knew of such a thing I do not know to this day. We motor sail to Santa Barbara Island spend a glorious three days hiking and watching the sea lions and brown pelicans in their own rookeries. 

We hoist Jim to the top of the mast to retrieve the halyard. Our bosun’s chair was actually a beach towel rolled up. Not quite OSHA approved. He retrieved the halyard. We were able to put the steering cables back onto the quadrant. 

Phase Five. We sailed back to the marina with following seas and brisk winds. I wouldn’t let anyone touch the helm as we served to down waves. I was addicted!

Phase Six. I took some very very basic lessons from Marina Sailing. They’d talk with you for a couple of hours and say good luck don’t hit anything. The next time they said you can go outside the breakwater but don’t go too far. And then I began chartering to Catalina and Santa Cruz and Anacapa and all of the beautiful Channel Islands. 

Phase Seven. Addicted as I was I did a flotilla in the British Virgin Islands. Then went back the next year and chartered my own boat. I took courses at Orange Coast College and I sailed multiple times monthly. 

Phase Eight. I purchased and outfitted a  Niagara 35 for Bluewater cuisine. I spent 2 1/2 glorious years gunkholing through Central and South America before running out of money.

Phase Nine. I launched a Sailing magazine- Southwinds – covering sailboat racing and cruising throughout the South. After 10 years in a labor of love I sold the magazine, got my ASA credentials and Coast Guard license, and here I am today. I spend more days on the water than I do off the water. Sailing changed my life forever in the most positive way possible.

“Born in Chicago.  Raised as an Air Force brat. Visited college in the sixties. Graduated in the 90’s. Corporate career in logistics. Discovered sailing in the 80’s. Bailed out and cruised from 1987 – 1991. Launched a sailing magazine in 1993 called “Southwinds.” Sailing correspondent for St. Petersburg Times. Sailed, raced (three national championships in Corsair trimarans).  Sold the magazine and became a USCG Master and ASA instructor in 2002.  Delivery skipper for broker and owners covering the Caribbean and Eastern Seaboard. Moved to Austin in 2017 as lead instructor for Outbound Sailing on Lake Travis (Austin). Enabling sailors. Now based in St. Petersburg, FL with my two rescue doggies. Sailing is my life.