Ahoy!
Now you can learn to sail and experience the thrill of the open water in just 3 days
even if you've never been on the water before.
Sailing might look complicated, but it’s easier than you think — especially when you’re learning hands-on. Our 3-day Skill Share lessons put you on a Hobie 16 with experienced sailors who love to teach. You’ll start with the basics, learn by doing, and feel the excitement of catching the wind for the first time. By the end of the weekend, you’ll have the confidence and knowledge to sail on your own — no prior experience required.
Why We're Different
Skill Share
At Sailably, we believe the best way to learn is from those who’ve already spent years on the water. That’s why our lessons are built around skill sharing — a simple, community-driven way to pass on real sailing experience from seasoned sailors to beginners.
Instead of formal classrooms or expensive certifications, we bring people together who love to sail and want to share what they know. You’ll learn the small things that only come from time at the helm — how to read the wind, feel the boat, and make confident decisions under sail.
Learn From Our Experience
Your Sailing Foundation Starts Here
Every great sailor starts with the basics. Our training is focused on the simple, practical skills that get you confidently sailing in just a few days.
Know Your Boat
Learn the parts of the Hobie 16 — hulls, trampoline, rudders, sails, and rigging — and how everything works together. Once you understand your boat, you’ll move with purpose and confidence every time you step aboard.
Points of Sail
We’ll show you how the wind powers your boat and how to adjust your sails for every direction you travel. You’ll practice sailing upwind, downwind, and across the breeze until reading the wind feels second nature. You'll learn all the lingo and be a salty dog in no time.
One With The Boat
Balance is everything. You’ll learn how to position your weight, move across the trampoline, and feel the boat’s response as it skims over the water. The goal is simple — become part of the boat so every turn, gust, and wave feels natural.
Safety & Recovery
Safety comes first. You’ll learn how to launch and land safely, handle changing conditions, and recover your boat after a capsize. These lessons build real confidence and prepare you for solo sailing.
(P.S. Yes you will get WET - and that's all part of the good, safe fun!)
A Community of Sailors, Teaching Together
Adm Perry
Capt Randy (Ret)
Harry "Sunny Jim"
FAQS
Do I need any prior sailing experience?
No experience is needed! Our lessons are designed for complete beginners. You’ll learn everything from the parts of the boat to handling wind and waves — all at your own pace.
Is there a cost to participate?
Lessons are completely free. Learn2Sail is a community Skill Share program supported by donations and partnerships. If you’d like to give back, you can donate gear, time, or boats to help others learn too.
Where do the lessons take place?
We hold monthly group lessons at various locations along the Gulf Coast — including Dunedin, Sarasota, Anna Maria Island, and Bradenton. Each spot offers easy beach access and great sailing conditions.
What kind of boats will we use?
We primarily use Hobie 16 catamarans — fast, fun, and perfect for learning. They’re stable enough for beginners yet exciting enough to keep things interesting.
What should I bring?
Bring a hat, sunscreen, water shoes, and a positive attitude. We’ll provide the boats, life jackets, and all the instruction you need.
Can I bring a friend or family member?
Absolutely! Sailing is more fun when shared. You can team up on the same boat or learn side-by-side with others. Just let us know when you register who all is in your party so we can accommodate everyone.
What happens if the weather is bad?
Safety always comes first. If wind or weather conditions aren’t ideal, we’ll reschedule or switch to a shore-based skills session to cover rigging, safety, and theory until conditions improve.
How long are the lessons?
Our group lessons usually run over a weekend — two full days of on-the-water and onshore learning. By Sunday, most participants are ready to sail independently.
Can I donate a boat or equipment?
Yes! We gratefully accept any boat in working condition. Donated boats are used for training and community lessons. Larger boats are used for our off-shore training and club getaways.
DEBRIEF
Crew Notes
I can't express how truly remarkable my experience with Learn2Sail was. I'm not too comfortable around the water so I was a bit apprehensive about getting on a small boat. I didn't need to worry at all! The lessons were paced just right and the capsize drill was actually what gave me the confidence to solo sail on Sunday.
Sally J.
The instructors were amazing and really loved what they do. Weather was perfect and the sailing area (Dunedin) was idyllic. I felt like I had walked into a Jimmy Buffet song. All that to say that I had the time of my life and I am a confident sailor thanks to you all.
Rodger P.
Get In Touch
