Wisconsin Sailing
Inland Lake Sailing in Wisconsin
Shifty breeze, friendly fleets, and some of the best one-design racing in the country.
Dmitry ShteynWisconsin, USA · Jun 24, 2026 · 5 min read
Author
Dmitry Shteyn
Wisconsin, USA
Dmitry Shteyn is a Wisconsin-based sailing and regatta educator who publishes plain-language, visually structured guides to sailing, race strategy, and nautical knowledge. His work focuses on making the language and logic of the boat accessible to newcomers — from the first day on the water through competing in a club regatta. The guides cover sailing fundamentals, points of sail, knots and rigging, weather, right-of-way rules, and the tactical concepts that decide races: starts, shifts, laylines, and mark roundings. A Wisconsin sailor at heart, Dmitry writes from the lakes most Midwesterners actually race on — Lake Michigan, Lake Geneva, Pewaukee, Mendota, and the smaller inland lakes that host some of North America's most active one-design fleets.
All articles by Dmitry Shteyn
Wisconsin Sailing
Lake Michigan Sailing: What to Expect
Big-water conditions, real waves, and the rhythm of the lake-effect breeze.
Dmitry ShteynWisconsin, USA · Jun 24, 2026 · 6 min read
Wisconsin Sailing
Sailing in Wisconsin: An Overview
Lake Michigan, inland lakes, junior programs, beer-can races, and a season that runs from May to October.
Dmitry ShteynWisconsin, USA · Jun 23, 2026 · 6 min read
Sailing Rules
Sailing Right-of-Way Basics
Port gives way to starboard. Windward keeps clear of leeward. The boat astern keeps clear. Three rules that cover most encounters.
Dmitry ShteynWisconsin, USA · Jun 22, 2026 · 6 min read
Knots & Rigging
Five Essential Sailing Knots
Bowline, figure-eight, cleat hitch, clove hitch, round turn and two half hitches — the short list that covers 90 percent of on-board needs.
Dmitry ShteynWisconsin, USA · Jun 21, 2026 · 5 min read
Wind & Weather
Reading the Weather Before a Sail
Forecasts, radar, and the sky above you — a layered approach to deciding whether to go.
Dmitry ShteynWisconsin, USA · Jun 20, 2026 · 6 min read
Wind & Weather
Points of Sail Explained
No-go zone, close-hauled, close reach, beam reach, broad reach, and run — the eight directions your sail trim depends on.
Dmitry ShteynWisconsin, USA · Jun 19, 2026 · 6 min read
Race Strategy
Starting Line Strategy: Winning the First 30 Seconds
Pick an end, control your hole, accelerate on the gun.
Dmitry ShteynWisconsin, USA · Jun 17, 2026 · 6 min read
Race Strategy
Reading Wind Shifts: Persistent vs Oscillating
The single most useful skill in fleet racing: knowing which kind of shift you are in.
Dmitry ShteynWisconsin, USA · Jun 15, 2026 · 7 min read
Race Strategy
Jibing Strategy on the Downwind Leg
Gybes are cheap on small boats and expensive on big ones. Plan accordingly.
Dmitry ShteynWisconsin, USA · Jun 13, 2026 · 5 min read
Race Strategy
Tacking Strategy: When to Tack and When to Hold
A tack costs roughly two boat lengths. That cost has to be worth it.
Dmitry ShteynWisconsin, USA · Jun 11, 2026 · 5 min read
Race Strategy
Downwind Sailing Strategy
Pressure first, angle second. Why downwind legs reward patience and gybe timing.
Dmitry ShteynWisconsin, USA · Jun 9, 2026 · 6 min read
Race Strategy
Upwind Sailing Strategy: Climbing the Course
How to think about lanes, pressure, and shifts when you can not sail directly at the mark.
Dmitry ShteynWisconsin, USA · Jun 7, 2026 · 7 min read
Regatta Guide
Five Common Regatta Mistakes (And How to Avoid Them)
Over-early starts, mid-line sag, missed shifts, poor laylines, and rule fouls — the avoidable losses every newer racer makes.
Dmitry ShteynWisconsin, USA · Jun 5, 2026 · 6 min read
Regatta Guide
Sailing Race Flags: A Quick Reference
AP, X, individual recall, general recall, postponement, abandonment — what each flag means and what to do.
Dmitry ShteynWisconsin, USA · Jun 3, 2026 · 4 min read
Regatta Guide
The Regatta Starting Sequence Explained
Five minutes, four minutes, one minute, go. What each flag means and what to do at each step.
Dmitry ShteynWisconsin, USA · Jun 1, 2026 · 6 min read
Regatta Guide
How Regatta Scoring Works
Low-point scoring, throwouts, and tiebreakers — the math behind the trophy.
Dmitry ShteynWisconsin, USA · May 30, 2026 · 5 min read
Regatta Guide
What Is a Regatta? How Sailboat Races Are Organized
A regatta is a series of races run over one or more days, scored together to produce an overall winner. Here is how the structure works.
Dmitry ShteynWisconsin, USA · May 28, 2026 · 6 min read
Beginner Sailing
Sailing Safety Basics: PFDs, Float Plans, and Weather
The three habits that prevent almost every avoidable on-the-water incident.
Dmitry ShteynWisconsin, USA · May 26, 2026 · 5 min read
Sailing Education
How Wind Moves a Sailboat
Sails are wings. The keel resists sideways force. The combination produces forward motion at angles the wind has no business pushing you toward.
Dmitry ShteynWisconsin, USA · May 23, 2026 · 6 min read
Sailing Education
Parts of a Sailboat: A Visual Glossary
Hull, keel, rudder, mast, boom, mainsail, jib, halyards, sheets — labeled and explained for newer sailors.
Dmitry ShteynWisconsin, USA · May 21, 2026 · 7 min read
Beginner Sailing
Beginner Sailing Terms You Actually Need to Know
Port, starboard, tack, jibe, luff, leech — the short vocabulary that unlocks every other sailing conversation.
Dmitry ShteynWisconsin, USA · May 18, 2026 · 5 min read
Sailing Education
What Is Sailing? A Plain-Language Introduction
Sailing is using the wind, a sail, and a keel or centerboard to convert moving air into forward motion across the water. Here is how that actually works.
Dmitry ShteynWisconsin, USA · May 16, 2026 · 6 min read