Learn to Sail
with Captain Dale
Private Instruction · Newport Beach, California
Private Instruction · Newport Beach, California
Your gateway to confident, capable sailing — from Newport Harbor to the open Pacific.
Whether you're dreaming of your first bareboat charter, planning a family cruising adventure, or looking to sharpen your coastal navigation skills, Captain Dale Winson brings the experience and teaching approach to get you there safely and confidently.
Dale's teaching draws from over 50,000 miles of real-world sailing — including 10,000 miles exploring the South Pacific, cruising Mexico's Sea of Cortez with his family, and competitive racing aboard championship-winning vessels. When you learn from Dale, you're learning from someone who has navigated challenging conditions, managed diverse vessels, and made countless real decisions far from shore.
With over 400 days captaining charter vessels from 35 to 73 feet, Dale understands exactly what sailors need to know. He builds skills progressively, safely, and enjoyably — whether you're seeking ASA certification or developing expertise for your own adventures.
Dale's teaching draws from decades of offshore sailing — including 10,000 miles in the South Pacific, the Sea of Cortez, coastal Mexico, and offshore racing. This isn't textbook knowledge. It's the hard-won judgment that only comes from real passages in real conditions.
Few instructors combine Dale's competitive racing background — including winning the Transpac race and crewing aboard 80-foot maxi yachts — with his deep family cruising experience. You'll develop both precision technique and practical judgment, in equal measure.
With over 400 days captaining charter vessels from 35 to 73 feet, Dale knows exactly what sailors actually need to know — and what they don't. He builds skills progressively and safely, whether you're after ASA certification or freedom on your own vessel.
Your first time on the water under sail. We cover the essentials — points of sail, basic boat handling, safety, and the language of sailing — in a relaxed, pressure-free environment aboard PatriciaAnn. You'll leave with genuine confidence and a real feel for the boat.
Build the skills to take a vessel out on your own. Navigation, weather awareness, anchoring, docking under sail, night operations, and VHF communication — structured around real Newport coastal conditions with an instructor who has done it thousands of times.
For sailors who have the coastal fundamentals and want to extend their range — to Catalina, the Channel Islands, Mexico, or the Pacific. Passage planning, offshore weather, watchkeeping, and the realities of bluewater sailing from someone who has crossed oceans with his family.
Not every sailor fits a program. Spinnaker handling, single-handed techniques, heavy weather preparation, boat systems, seamanship for a specific passage — if you have a goal, Dale will design a session around it. Couples and small groups welcome.
"So you want to live aboard and sail around the world — what now?"
Dale has sailed thousands of miles with his family, exploring remote anchorages and navigating challenging passages from Mexico to the South Pacific. He can guide you through everything aspiring cruisers need to know — not from a textbook, but from experience living it.
Whether you're planning a coastal cruise or a circumnavigation, Dale helps transform your dream into a practical, achievable reality.
Start the ConversationLearn from a captain who has sailed the world — and can help you do the same.