Learn to Sail

Sailing Lessons on Sunfish sailboats,
Or on a very stable WindRider 17 Trimaran with a quiet electic motor for uncertain breezes
Or on your own sailboat or powerboat.
By appointment only.

Private Sailing Lessons for all skill levels. Sailing Instruction is customized for each person to ensure a pleasant and safe sailing experience. Captain and Coach Jay Winters can usually teach a new student to sail a Sunfish in three to four hours. For the experienced sailor, coached/guided sails are also offered. Jay is fully vaccinated.

Coach Jay only gives one sailing lesson a day. He will look at the weather forcast and try to scehedule with the best wind and tide conditions for your session, Then he will make a special trip from his home in Bradenton to Bimini Bay just to work with you. Please arrive for your appointments on time or be sure to call ASAP if a delay or an emergency occurs.

The First Hour of instruction is often taught with the student in shallow water, while the coach goes over basic parts of a sailboat, rigging, basic sailing theory, turning (tacking and jibing), points of sail, avoiding a capsize, capsize recovery, getting out of a stall and more.

After a very short break, The Second Hour will be spent with the coach and the student sailing on the same boat, while the student is in control of both the tiller and the sail. The Third Hour will often be spent with the student sailing on his/her own, as the instructor coaches the student(s) from a central location or follows on another Sunfish or on a kayak. If desired, you can sail an additional 40 minutes during the same day for $40 extra.

It is recommended that you schedule an additional session on another day to head out the channel into the beautiful Tampa Bay as we cover additional techniques such as advanced Sail Trim, man/woman or object Overboard Drills, planning for Emergencies, Aids to Navigation, Right of Way Rules, Returning to port upwind vs downwind... and most of all, an opportunity to feel the enjoyment and magic of sailing. During the second session we often sail to the Anna Maria Pier and pull up on shore for a brief snack. Then we are back on the near shore open waters of Tampa Bay before we return to Bimini Bay. During the second session, we can sail in one boat together or in two separate boats.

See video below of a 9-year-old new Bimini Bay Sailor.

I recommend you purchase the inexpensive PDF or Kindle Sailboat manual shown below. It emphasizes Sunfish. The more you know before you start, the more pleasant the experience and the sooner you will be able to sail solo.

Cost for Sailboat Lessons:

  • $240 for a standard 3-hour Sunfish lesson.
  • $290 for 2 students at the same time on 1 boat.
    (This works well even for adults.)
  • $340 for 2 to 3 students on 2 different boats the 3rd hour.
  •   $40 extra for 40 extra minutes on 1 boat.
  •   $80 extra for 40 extra minutes on 2 boats.

Cash, check with ID, or Card (see Rates page)
Click for ATMs on Anna Maria Island.

Cost for 1-hour Lesson on Knots:
$40 for one to three students.
Deck cleat, Bowline, Figure 8, Hitch, Slip Knot...

Prepare, Learn or Review: Purchase Small Sailboats Made Fun and Easy with Memory Tips, by Captain and Coach Floyd Jay Winters, for only $9.95. This Sunfish and small sailboat eBook is a 170-page PDF file for your PC or iPad. It is also available in Kindle, Audio and Print formats. It is filled with over 200 well labeled photos and illustrations, easy-to-understand terms, and safety tips. It even includes a Sea of Water Riddles that are splashed throughout the book to make the reading even more entertaining for friends or family.

What to bring with you:
Hat, Sunscreen, Water Shoes, Water/Gatorade, a Snack

Be safe - wear Water Shoes!
You can buy Water Shoes at:
Sun and Surf 5418 Marina Dr, Holmes Beach
Island Trader 5336 Gulf Dr, Holmes Beach
Walmart, West Marine...

Coach Jay will be with you the entire time.
But below are Pointers to Stay Safe:

  • Always let someone know your sail plans
  • Beginners - start by sailing upwind
  • Stay relatively close to shore
  • Only go out if sure you can get back
  • Check Wind & Tide at bottom of page
  • Head to shore if dark clouds start to build
  • Do not go out to the Gulf of Mexico
  • To avoid a capsize:
    A. Hike or lean to the High side
    B. Ease the Mainsheet slightly
    C. Move Tiller a tad toward the sail to head slightly upwind