Randy Deering

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Maritime Services

As you can see, I love the water! I love looking at it and particularly, being on it. What I really love is helping people to become sailors and to enjoy their boats.

American Sailing Association Instructor

Randy Deering has been teaching people to sail professionally for nearly 15 years. In that time, he has given instruction to more than 200 people, from 13 to 80 years old. He is certified to teach through ASA Level 104.

ASA 101

Basic Keelboat Sailing: the language of sailing; parts of the boat; points of sail; navigation rules; safety; maneuvering and docking under power; basic knots; lateral aids

ASA 103

Basic Cruising: boat handling under power and sail; anchoring; reefing; person overboard drill; compass course; weather and seamanship

ASA 104

Charter Boat Sailing: boat systems; provisioning; course plotting and chart work; knots and hitches; refueling and pump out

Each of these courses take an average of two days including classroom as well as on-the-water teaching and evaluation ending with a written exam. I focus on imparting confidence as well as competence and always have a good time doin it.


Randy has captained a great many day charters for private and corporate functions on and around Tampa Bay. He has also done numerous corporate leadership building flotillas. (see Leadership Consulting)

Boat Deliveries

Including the following:

  • Irwin 52 Ketch from Tampa Bay to Pensacola, FL
  • Gulfstar 47 Ketch from Dominican Republic to Bradenton, FL
  • CT 41 Ketch from Tampa Bay to Houston, TX
  • Pacific Seacraft 32 from Ft. Lauderdale to St. Petersburg, FL
  • Numerous deliveries along FL Suncoast

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