Sailing Lessons

We are all about service and are open to customize your sail with any special request. Just let us know what you have in mind and we will do our utmost to accommodate your interest.

Summer Specials

"A great way to spend an afternoon or evening"


My wife and I went on two charters with Capt. Jack . What a wonderful guide. He knows the area well. On the first sail we went to an island where we swam, snorkeled, and ate. The second sail was a sunset cruise. The sunset was beautiful. Capt. Jack told many entertaining stories about his sailing adventures. He has sailed solo for over 6 months. This was a very valuable experience and time well spent for us.

Sebastian222,- Orlando Florida         

Personalized Service

"Nice boat, great views, schedule some wind"


Capt. Jack did a great job with what he had to work with. He was cordial and offered us beverages. The boat was clean and a good size for 4 guests. We ended up seeing over a dozen dolphins. The day we went was sunny, but the wind was against us. In the inter-coastal it was difficult to tack and stay in deeper water, so we motored a fair bit. Once we got out the Clearwater pass it was clear sailing. In summery , good price, pleasant captain, nice boat. I would go back.

Erik M- Detroit, Michigan 

About Jack Sailing- Yacht Charters

Captain Jack enjoys sharing his passion for sailing and has been boating for over 50 years. His beginning starts from boating on the great lakes when he was a child. Over 20 years ago he moved to Florida and his hobby of sailing became full time. He is actively a member of several Yacht Clubs, U.S.C.G, former captain of Encore sailing, Conch Charters, Sailing Florida and has sailed the Caribbean extensively. From  boat deliveries, weddings at sea, romantic moonlight sails, celebrations ,ashes at sea, he still enjoys it all.    U.S. Coast Guard Licensed.    

"Great Half day with Family"

My husband and I took our adult kids out for several hours. Captain Jack  took us through the waterway past Dunedin and out into the Gulf around Clearwater . Beautiful sailing, beautiful view and great time to be with our kids and their partners. I highly recommend this company. I felt the captain was a expert sailor and was courteous and warm. Best part is the boat only takes 6 passengers so you do not need to share space with overly drunk and loud others-its private

Becky S -Pottstown, Pennsylvania 

Book your Sail for this summer today, and save 25%. We're offering early booking discounts for July and August. Simply mention code SUMMERTIME when you call one of our Sail concierges.

Jacks Sailing Charters


Jack Sailing offers sailing lessons for both the beginner and advanced sailor. We can offer mono-hull and multi-hull training. So give us a call and we can custom accommodate your desire to start sailing today.