Learn to Sail

Sailing Lessons on Sunfish Sailboats
Or on a very stable WindRider 17 Trimaran
Or on your own sailboat or powerboat.

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. Lessons and coached/guided sails can also be offered on the very stable WindRider 17 Trimaran. (Jay is fully vaccinated.)

Jay will make a special trip 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.

An additional 40 minutes during the same day ($40) or an additional session on another day may be scheduled to head out the channel into the beautiful Tampa Bay and cover additional techniques such as advanced Sail Trim, man/woman or object Overboard Drills, planning for Emergencies, Aids to Navigation, Right of Way Rules, Anchoring Tips, Returning to port,... and most of all, an opportunity to feel the enjoyment and magic of sailing.

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.
  •   $20 for a tandem kayak while kids/spouse get lessons.

  • $330 for a WindRider 17 Triamaran lesson or coached 3-hour sail (up to 3 people).

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. The sailing made fun eBook is a 170-page PDF file, (also available in Audio, Kindle and Print formats) 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, a small 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 to the High side
    B. Ease the Mainsheet slightly
    C. Head slightly upwind